CN109503562B - 2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof - Google Patents
2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof Download PDFInfo
- Publication number
- CN109503562B CN109503562B CN201811604657.3A CN201811604657A CN109503562B CN 109503562 B CN109503562 B CN 109503562B CN 201811604657 A CN201811604657 A CN 201811604657A CN 109503562 B CN109503562 B CN 109503562B
- Authority
- CN
- China
- Prior art keywords
- atom
- reaction
- thienyl
- pyrimidyl
- mixed solution
- 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.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a 2- [4- (2-thienyl)]The structural general formula of the pyrimidyl urea derivative is as follows:in the general formula R1Is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, methoxy group, R2Hydrogen atom, chlorine atom, bromine atom, methyl. The present application providesCompounds 2- [4- (2-thienyl) are synthesized by introducing thiophene ring and amide into the molecular structure of pyrimidine]A pyrimidyl urea derivative. The compound has simple structure, has better poisoning effect on the storage pests, has better inhibitory activity on plant pathogenic bacteria, and lays a good foundation for the creation of new pesticides.
Description
Technical Field
The invention relates to the technical field of pesticides, and particularly relates to a 2- [4- (2-thienyl) ] pyrimidyl urea derivative and a preparation method and application thereof.
Background
The amide compounds have wide biological activity, including sterilization, antioxidation, plant growth regulation and the like. Therefore, extensive and intensive research on the compounds has been conducted over the past decades, and many novel and highly effective compounds have been discovered, and there have been continuously reported varieties which are novel in structure, unique in mode of action, excellent in performance, highly effective against harmful organisms, safe against non-target organisms, easily degradable in the environment, and safe in the human health and ecological environment as degradation products.
The pyrimidine is a very important heterocyclic compound and is widely applied to the fields of medicines, pesticides, daily chemicals and the like. A large number of researches show that the compounds have good biological activity, such as insecticidal activity, bactericidal activity, acaricidal activity, weeding activity, plant growth regulation activity, antiviral activity, anticancer activity, antioxidant activity, anti-inflammatory activity and the like. Because the pyrimidine compounds have the advantages of high efficiency, low toxicity to human and livestock, unique action mode, difficult generation of drug resistance of pests and the like, the molecular structure design, synthesis and biological activity research are very active fields in the heterocyclic compound research, and the compounds with novel and simple structure and good biological activity are continuously generated.
Thiophene is an important member of heterocyclic compounds and plays a very important role. The study of thiophene derivatives also has a very major role in medicine and agrochemical chemistry. Thiophene derivatives have a wide variety of biological activities, for example, antibacterial, antiviral, antitumor, anti-inflammatory, insecticidal, herbicidal, and the like. Meanwhile, the thiophene ring-containing compounds generally have the characteristics of high efficiency, low toxicity, safety to non-target organisms, easiness in degradation in the environment, difficulty in generation of resistance by pests and the like, and compounds with novel structures and excellent performance are continuously published. Therefore, in the process of research and development of pesticides, compounds containing thiophene rings are more widely concerned and become hot spots and frontiers for creating new pesticides.
To date, the use of 2- [4- (2-thienyl) ] pyrimidyl urea derivatives as agricultural insecticides and fungicides has not been reported.
Disclosure of Invention
The invention aims to provide a novel compound used as an agricultural insecticide and a bactericide and a preparation method of the compound.
A2- [4- (2-thienyl) ] pyrimidyl urea derivative has a structural general formula as follows:
r in the general formula (I)1Is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, methoxy group, R2Hydrogen atom, chlorine atom, bromine atom, methyl.
A preparation method of 2- [4- (2-thienyl) ] pyrimidyl urea derivatives comprises the following steps: dissolving substituted acetophenone in anhydrous ethanol, adding 10% NaOH solution, stirring in ice bath, slowly dropping the mixed solution of thiophene-2-formaldehyde and anhydrous ethanol or 5-bromothiophene-2-formaldehyde and anhydrous ethanol into the mixed solution with a constant pressure dropping funnel, reacting at 0-5 deg.C, and checking whether the reaction is completed with thin-layer silica gel plate (TLC). After completion of the reaction, a 3X molecular sieve was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, followed by reaction at 40 to 50 ℃ and completion of the reaction was checked by TLC. And after the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain the target compound.
Further, according to the method, the substituted acetophenone is one of 4-chloroacetophenone, 4-bromoacetophenone, 4-methoxyacetophenone and 4-methylacetophenone.
Further, in the method described above, the 13X molecular sieve is 40-60 mesh.
An application of 2- [4- (2-thienyl) ] pyrimidyl urea derivative as agricultural insecticide or bactericide.
Further, as the above-mentioned application, the pesticide can kill one or more of corn elephant, corn bagel and corn beetle.
Further, the bactericide can inhibit one or more of bacterial brown spot of corn, bacterial black spot of rape, citrus canker, potato black shank, onion bulb rot and melon bacterial fruit blotch.
Has the advantages that:
the invention introduces thiophene ring and amide into the molecular structure of pyrimidine to synthesize some 2- [4- (2-thienyl) ] pyrimidyl urea derivatives. The derivative has simple structure and excellent activity, and can lay a good foundation for creating new pesticides.
The compound of the general formula (I) has simple synthesis process, and adopts a one-pot method, namely, the intermediate is not separated out according to the traditional method and then subjected to the next reaction, but the next reaction is directly performed, so that the operation steps are reduced, the reaction efficiency is improved, and the energy conservation and consumption reduction are facilitated. The compound of the general formula (I) has better control effect on storage pests and plant pathogenic bacteria, and is not reported in the currently known pesticides and bactericides.
Drawings
FIG. 1 is a hydrogen spectrum of the compound prepared in example 1;
FIG. 2 is a carbon spectrum of the compound prepared in example 1;
FIG. 3 is a high resolution mass spectrum of the compound prepared in example 1;
FIG. 4 is a hydrogen spectrum of the compound prepared in example 2;
FIG. 5 is a carbon spectrum of the compound prepared in example 2;
FIG. 6 is a high resolution mass spectrum of the compound prepared in example 2;
FIG. 7 is a hydrogen spectrum of the compound prepared in example 3;
FIG. 8 is a carbon spectrum of the compound prepared in example 3;
FIG. 9 is a high resolution mass spectrum of the compound prepared in example 3;
FIG. 10 is a hydrogen spectrum of the compound prepared in example 4;
FIG. 11 is a carbon spectrum of the compound prepared in example 4;
FIG. 12 is a high resolution mass spectrum of the compound prepared in example 4;
FIG. 13 is a hydrogen spectrum of the compound prepared in example 5;
FIG. 14 is a carbon spectrum of the compound prepared in example 5;
FIG. 15 is a high resolution mass spectrum of the compound prepared in example 5.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention are described below clearly and completely, and it is obvious that the described embodiments are some, not all embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a compound with insecticidal and bacteriostatic activity, which has the following structural general formula:
r in the general formula (I)1Is fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, methoxy group, R2Hydrogen atom, chlorine atom, bromine atom, methyl.
The main reaction equation in the preparation of the compound of formula (I) is:
in the formula R1、R2The same as above.
The compound of the general formula (I) has simple synthesis process, and adopts a one-pot method, namely, the intermediate is not separated out according to the traditional method and then subjected to the next reaction, but the next reaction is directly performed, so that the operation steps are reduced, the reaction efficiency is improved, and the energy conservation and consumption reduction are facilitated. The compound of the general formula (I) has better control effect on storage pests and plant pathogenic bacteria, and is not reported in the currently known pesticides and bactericides.
Example 1:
0.02mol of 4-chloroacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of a 10% NaOH solution was added thereto. Under stirring in an ice bath, a mixed solution of 0.02mol of thiophene-2-carbaldehyde and 20mL of absolute ethanol was slowly dropped into the above mixed solution with a constant pressure dropping funnel, reacted at 0 to 5 ℃, and checked for completion with a thin layer silica gel plate (TLC). After completion of the reaction, 2 g of a 13X molecular sieve (40-60 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, reacted at 40-50 ℃ and checked for completion by TLC. After the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain a dark green powdery solid product, wherein the yield is 87%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):9.64(1H,s),8.49(1H,s),8.33(2H,dd,J1=8.8Hz,J2=8.8Hz),8.29(1H,dd,J1=0.8Hz,J2=0.8Hz),8.15(1H,s),7.88(1H,dd,J1=0.8Hz,J2=0.8Hz),7.43(2H,t,J=8.8Hz),7.31(2H,dd,J1=4.0Hz,J2=4.0Hz);13C NMR(100MHz,DMSO-d6)δ(ppm):164.15,160.01,158.82,155.17,142.07,131.69,130.23,130.14,130.02,129.50,116.47,116.26,104.44;HRMS(ESI)m/z:Calcd for C15H11N4OSCl[M+Na]+:353.0235,Found:353.0232
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in figures 1-3.
Example 2:
0.02mol of 4-methylacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of a 10% NaOH solution was added thereto. Under stirring in an ice bath, a mixed solution of 0.02mol of thiophene-2-carbaldehyde and 20mL of absolute ethanol was slowly dropped into the above mixed solution with a constant pressure dropping funnel, reacted at 0 to 5 ℃, and checked for completion with a thin layer silica gel plate (TLC). After completion of the reaction, 2 g of a 13X molecular sieve (40-60 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, reacted at 40-50 ℃ and checked for completion by TLC. After the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain a light yellow powdery solid product, wherein the yield is 86%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):9.56(1H,s),8.55(1H,s),8.28(1H,d,J=3.6Hz),8.16(2H,d,J=8.0Hz),8.11(1H,s),7.86(1H,d,J=4.8Hz),7.39(2H,d,J=8.0Hz),7.30(2H,t,J1=4.0Hz,J2=4.0Hz),2.41(3H,s);13C NMR(100MHz,DMSO-d6)δ(ppm):165.12,159.89,158.83,155.23,142.19,141.91,133.65,131.54,129.97,129.85,129.46,127.63,104.22,21.50;HRMS(ESI)m/z:Calcd for C16H14N4OS[M+Na]+:333.0781,Found:333.0759.
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in FIGS. 4-6.
Example 3:
0.02mol of 4-methoxyacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of a 10% NaOH solution was added thereto. Under stirring in an ice bath, a mixed solution of 0.02mol of thiophene-2-carbaldehyde and 20mL of absolute ethanol was slowly dropped into the above mixed solution with a constant pressure dropping funnel, reacted at 0 to 5 ℃, and checked for completion with a thin layer silica gel plate (TLC). After completion of the reaction, 2 g of a 13X molecular sieve (40-60 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, reacted at 40-50 ℃ and checked for completion by TLC. After the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain a white solid product, wherein the yield is 87%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):9.62(1H,s),8.47(1H,s),8.31(2H,dd,J1=8.8Hz,J2=8.8Hz),8.26(1H,dd,J1=0.8Hz,J2=0.8Hz),8.13(1H,s),7.85(1H,dd,J1=0.8Hz,J2=0.8Hz),7.41(2H,t,J=8.8Hz),7.29(2H,dd,J1=4.0Hz,J2=3.6Hz),3.88(3H,s);13C NMR(100MHz,DMSO-d6)δ(ppm):165.34,162.97,159.48,156.33,155.83,151.81,147.25,129.83,129.14,115.31,114.46,113.81,103.91,56.43;HRMS(ESI)m/z:Calcd for C16H14N4O2S[M+Na]+:349.0731,Found:349.0759.
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in FIGS. 7-9.
Example 4:
0.02mol of 4-methylacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of a 10% NaOH solution was added thereto. Under stirring in an ice bath, a mixed solution of 0.02mol of 5-bromothiophene-2-carbaldehyde and 20mL of absolute ethyl alcohol was slowly dropped into the mixed solution by using a constant pressure dropping funnel, the reaction was carried out at 0 to 5 ℃, and whether the reaction was completed or not was checked by using a thin layer silica gel plate (TLC). After completion of the reaction, 2 g of a 13X molecular sieve (40-60 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, reacted at 40-50 ℃ and checked for completion by TLC. After the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain a gray solid product, wherein the yield is 86%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):9.60(1H,s),8.41(1H,s),8.14-8.11(4H,m),7.44(1H,d,J=4.0Hz),7.39(2H,d,J=8.0Hz),7.22(1H,s),2.41(3H,s);13C NMR(100MHz,DMSO-d6)δ(ppm):165.23,158.99,158.76,155.09,143.86,142.05,133.53,132.90,130.50,129.99,127.62,117.51,103.82,21.50;HRMS(ESI)m/z:Calcd for C16H13N4OSBr[M+Na]+:410.9886,Found:410.9888.
the hydrogen spectrum, carbon spectrum and high resolution mass spectrum of the product are shown in FIGS. 10-12.
Example 5:
0.02mol of 4-bromoacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of a 10% NaOH solution was added thereto. Under stirring in an ice bath, a mixed solution of 0.02mol of 5-bromothiophene-2-carbaldehyde and 20mL of absolute ethyl alcohol was slowly dropped into the mixed solution by using a constant pressure dropping funnel, the reaction was carried out at 0 to 5 ℃, and whether the reaction was completed or not was checked by using a thin layer silica gel plate (TLC). After completion of the reaction, 2 g of a 13X molecular sieve (40-60 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of guanylurea sulfate and 20mL of anhydrous ethanol was slowly dropped into the mixture using a constant pressure dropping funnel, reacted at 40-50 ℃ and checked for completion by TLC. After the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain a white powdery solid product, wherein the yield is 84%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):9.67(1H,s),8.32-8.29(3H,m),8.15(1H,s),8.13(1H,d,J=4.0Hz),7.47-7.42(4H,m);13C NMR(100MHz,DMSO-d6)δ(ppm):164.70,159.47,158.41,154.80,141.77,141.49,133.23,131.11,129.55,129.43,129.04,127.21,103.80;HRMS(ESI)m/z:Calcd for C15H10N4OSBr2[M+Na]+:474.8834,Found:474.8838.
the hydrogen spectrum, carbon spectrum and high resolution mass spectrum of the product are shown in FIGS. 13-15.
Example 6: determination of insecticidal Activity of Compounds of the present invention
(1) Test pest
Adult corn weevils, adult corn clothes and adult tribolium castaneum, which are all sensitive strains bred indoors for years.
(2) Measurement method
Adopting a feed mixing method: mixing the compound to be tested and the wheat feed uniformly according to a certain dosage. Weighing 100 g of the drug-mixed feed into 500mL wide-mouth bottles, putting 30 heads of tested pests into each bottle, wrapping the bottle mouth with white cloth, placing the bottles in a pest feeding room with the temperature of 28-30 ℃ and the relative humidity of 70-80% for continuous feeding, and taking the feed without the drug as a blank control. Mortality was recorded after 14 days, each experiment was repeated 3 times, and corrected mortality was calculated using the following formula:
(3) results of the experiment
The insecticidal results of the compounds of the present invention are shown in table 1.
TABLE 1 poisoning Activity of Compounds of the invention against storage pests
a: average of three replicates.
From Table 1 above, it is clear that the compounds of the present invention have a good poisoning activity against these pests.
Example 7: determination of the bacteriostatic Activity of Compounds of the invention
(1) Test for plant pathogenic bacteria
Bacterial brown spot of corn, bacterial black spot of rape, canker of citrus, black shank of potato, bulb rot of onion, and bacterial fruit blotch of melon.
(2) Measurement method
(a) Activation of strains: the bacterial strain to be tested is inoculated on a beef extract peptone solid medium slant and cultured overnight at 37 ℃.
(b) Preparation of bacterial suspension: inoculating a loop of activated test strain in a conical flask containing 100mL beef extract peptone liquid medium, culturing at 37 deg.C for 18h to obtain initial bacterial suspension, and diluting with sterile normal saline to appropriate concentration (10)6~107CFU/mL) of the suspension.
(c) Determination of Minimum Inhibitory Concentration (MIC): dissolving the test compound in dimethyl sulfoxide, diluting with sterile normal saline containing 0.1% Tween-80 by two-fold dilution method to obtain solutions with different concentrations, and mixing. 1mL of the diluted sample solution was added to 19mL of a sterilized medium, and mixed well to prepare a plate. After the culture medium has solidified, the above-mentioned concentration of 10% is added by coating method6And culturing 200 mu L of CFU/mL bacterial suspension at 37 ℃ for 16-18 h, observing the growth condition of bacteria, taking the concentration of completely sterile growth as the MIC value of the test sample solution, and taking the corresponding solution without the test compound as a blank control.
(3) Results of the experiment
The bacteriostatic activity of the compounds of the invention is shown in table 2.
TABLE 2 inhibitory Activity of the Compounds of the present invention against plant pathogenic bacteria
From the above table 2, it can be seen that the compounds of the present invention have a good inhibitory effect on these plant pathogenic bacteria.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (4)
2. The process for the preparation of 2- [4- (2-thienyl) ] pyrimidylurea derivatives according to claim 1, wherein: dissolving substituted acetophenone in anhydrous ethanol, wherein the substituted acetophenone is one of 4-chloroacetophenone, 4-bromoacetophenone, 4-methoxyacetophenone and 4-methylacetophenone, adding 10% NaOH solution, slowly dropping a mixed solution of thiophene-2-formaldehyde and anhydrous ethanol or a mixed solution of 5-bromothiophene-2-formaldehyde and anhydrous ethanol into the mixed solution by using a constant pressure dropping funnel under the stirring of ice bath, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate. After the reaction, adding a 3X molecular sieve into the reaction mixture, slowly dropping a mixed solution of 0.02mol guanylurea sulfate and 20mL absolute ethyl alcohol into the mixture by using a constant pressure dropping funnel, reacting at 40-50 ℃, and detecting whether the reaction is finished by TLC; and after the reaction is finished, filtering, adding a large amount of ice water into the filtrate, adjusting the pH value to be neutral by using a 10% hydrochloric acid solution, separating out a precipitate, filtering, washing, and recrystallizing by using absolute ethyl alcohol to obtain the target compound.
3. The method of claim 2, wherein the 13X molecular sieve is 40-60 mesh.
4. Use of a 2- [4- (2-thienyl) ] pyrimidyl urea derivative according to claim 1 as an agricultural pesticide for killing one or more of elephant corn, clothes of corn and corn beetle.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811604657.3A CN109503562B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811604657.3A CN109503562B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109503562A CN109503562A (en) | 2019-03-22 |
CN109503562B true CN109503562B (en) | 2022-01-14 |
Family
ID=65754821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811604657.3A Active CN109503562B (en) | 2018-12-26 | 2018-12-26 | 2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109503562B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7085697B2 (en) * | 2019-11-01 | 2022-06-16 | ユニマテック株式会社 | Fluorine-containing pyrimidine compound and its production method |
CN113354573B (en) * | 2021-06-30 | 2023-03-17 | 河南阿尔法医药科技有限公司 | Method for large-scale production of alpha, alpha-terpyridine |
CN113831328B (en) * | 2021-09-30 | 2023-12-01 | 南京林业大学 | 6- (benzo 1, 3-dioxy pentacyclic) -4-phenylpyrimidine amide derivative, and preparation method and application thereof |
-
2018
- 2018-12-26 CN CN201811604657.3A patent/CN109503562B/en active Active
Non-Patent Citations (8)
Title |
---|
Chen, Wei,等.Synthesis and evaluation of novel N-(4’-arylpyrimidin-2’-yl) sulfonylurea derivatives as potential antifungal agents.《Chem. Res. Chin. Univ.》.2015,第31卷(第2期),第218-223页. * |
N-(4-’芳环取代嘧啶基-2’-基)-2-乙氧羰基苯磺酰脲衍生物的合成及抑菌活性;刘卓,等;《高等学校化学学报》;20130831;第34卷(第8期);第1868-1872页 * |
NOVEL MONOCYCLIC β-LACTUM MOLECULES: DESIGNED AND CHARACTERIZED AS POSSIBLE ANTIBACTERIAL AGENTS;Vikas A. Desai,等;《World Journal of Pharmaceutical Research》;20161231;第5卷(第4期);第1943-1950页 * |
Shah, Tejaskumar J.,等.Synthesis of some novel fluorinated 4-thiazolidinones containing amide linkages and their antimicrobial screening.《ARKIVOC》.2007,第218-228页. * |
Synthesis and evaluation of novel N-(4’-arylpyrimidin-2’-yl) sulfonylurea derivatives as potential antifungal agents;Chen, Wei,等;《Chem. Res. Chin. Univ.》;20151231;第31卷(第2期);第218-223页 * |
Synthesis of some novel fluorinated 4-thiazolidinones containing amide linkages and their antimicrobial screening;Shah, Tejaskumar J.,等;《ARKIVOC》;20071231;第218-228页 * |
Vikas A. Desai,等.NOVEL MONOCYCLIC β-LACTUM MOLECULES: DESIGNED AND CHARACTERIZED AS POSSIBLE ANTIBACTERIAL AGENTS.《World Journal of Pharmaceutical Research》.2016,第5卷(第4期),第1943-1950页. * |
刘卓,等.N-(4-’芳环取代嘧啶基-2’-基)-2-乙氧羰基苯磺酰脲衍生物的合成及抑菌活性.《高等学校化学学报》.2013,第34卷(第8期),第1868-1872页. * |
Also Published As
Publication number | Publication date |
---|---|
CN109503562A (en) | 2019-03-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106588772B (en) | Heavy turpentine longifolene derivative and preparation and application thereof | |
CN106432237B (en) | Amidine compound of the one kind containing two chiral centres synthesizes and purposes | |
CN109503562B (en) | 2- [4- (2-thienyl) ] pyrimidyl urea derivative and preparation method and application thereof | |
EA026369B1 (en) | Pest control composition including novel iminopyridine derivative | |
CN109942561B (en) | 4- (2-thienyl) pyrimidine derivative and preparation method and application thereof | |
CN103664808B (en) | A kind of aryl 3-triazole compounds containing chlorocyclopropane and preparation method thereof and application | |
CN103214461B (en) | Quinoline derivative and application thereof | |
CN103755700B (en) | A kind of pyrazol acid amide compounds and uses thereof | |
CN109824742A (en) | A kind of trehalase inhibitor and preparation method thereof | |
CN109535136B (en) | 2- [4- (2-furyl) ] pyrimidylurea compound and preparation method and application thereof | |
CN109535142B (en) | 2- (1-pyrazolyl) pyrimidine derivative and preparation method and application thereof | |
CN109400591B (en) | 4- (2-furyl) pyrimidine compound and preparation method and application thereof | |
CN109535135B (en) | 2-methylpyrimidine compound and preparation method and application thereof | |
CN112956483B (en) | Compound phytocin A for inhibiting growth of weed seeds | |
CN103304553B (en) | 2-(propylene-2-yl)-2,3-dihydro-4-benzofuranol as well as preparation method and application thereof | |
BR102013027162B1 (en) | METAL AND NARINGIN AND NARINGENIN COMPLEXES AND INSETICATED COMPOSITIONS FOR THE CONTROL OF URBAN PEST INSECTS, AGRICULTURE AND FORESTRY FIELD OF THE INVENTION | |
CN108117528B (en) | 2, 5-substituent-1, 3, 4-oxadiazole sulfone derivative, preparation method and application thereof | |
CN108794461B (en) | Fluorine-containing phenyl oxadiazole pyrazole insecticidal bactericide | |
CN105541795B (en) | Pyridyl-pyrimidine class compound and its synthetic method and application | |
CN102827025B (en) | 2-methoxy-N-(4-fluorophenyl) benzamide as well as preparation method and application of 2-methoxy-N-(4-fluorophenyl) benzamide | |
CN111892510B (en) | N- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide and use thereof | |
CN109897005B (en) | Phenyl pyrimidine analogue containing substituted phenoxy, preparation method and application thereof | |
CN103288810A (en) | Cyclopropyl derris hydrazide, and preparation method and application thereof | |
JP2020506891A (en) | Aziridine spinosyn derivatives and production method | |
CN115536586B (en) | Pyrazole amide compound as well as preparation method and application thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |