CN109942561B - 4- (2-thienyl) pyrimidine derivative and preparation method and application thereof - Google Patents
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Abstract
The invention provides a 4- (2-thienyl) pyrimidine derivative, a preparation method and application thereof, wherein the general structural formula 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 compound provided by the application introduces a thiophene ring into the molecular structure of pyrimidine, and synthesizes a plurality of 4- (2-thienyl) pyrimidine derivatives. 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 4- (2-thienyl) pyrimidine derivative and a preparation method and application thereof.
Background
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, there has been no report of the use of 4- (2-thienyl) pyrimidine derivatives as agricultural insecticides and fungicides.
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.
A4- (2-thienyl) pyrimidine derivative has the following structural 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.
A method for preparing a 4- (2-thienyl) pyrimidine derivative: dissolving substituted acetophenone in anhydrous ethanol, adding 10% NaOH solution, stirring in ice bath, slowly dropping the mixture of 5-bromothiophene-2-formaldehyde and anhydrous ethanol or the mixture of thiophene-2-formaldehyde and anhydrous ethanol into the mixed solution with a constant pressure dropping funnel, reacting at 0-5 deg.C, and checking (TLC) with a thin-layer silica gel plate to determine whether the reaction is completed. After the reaction was completed, a 4A molecular sieve was added to the reaction mixture, and a mixed solution of acetamidine hydrochloride and absolute 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, the 4A molecular sieve is 80-100 meshes.
An application of 4- (2-thienyl) pyrimidine derivatives as agricultural insecticides or bactericides.
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 into the molecular structure of pyrimidine to synthesize some 4- (2-thienyl) pyrimidine derivatives, and the compounds have simple structure and excellent activity, and can lay a good foundation for the creation of 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:
compound (I)
Preparation of
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 4A molecular sieve (80-100 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of acetamidine hydrochloride 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 needle-shaped crystal product, wherein the yield is 83%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):8.42(1H,s),8.36(2H,d,J＝8.4Hz),8.29(1H,dd,J1＝1.2Hz,J2＝1.2Hz),7.85(1H,dd,J1＝1.2Hz,J2＝0.8Hz),7.65(2H,d,J＝8.8Hz),7.29(1H,dd,J1＝3.6Hz,J2＝4.0Hz),2.68(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):168.14,162.66,160.03,142.66,136.35,135.62,131.59,129.58,129.43,129.42,129.30,108.17,26.37；HRMS(ESI)m/z:Calcd for C15H11N2SCl[M+H]+:287.0404,Found:287.0410.
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in figures 1-3.
Example 2:
compound (I)
Preparation of
0.02mol of 4-methylacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of 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 4A molecular sieve (80-100 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of acetamidine hydrochloride 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 crystal product, wherein the yield is 90%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):8.34(1H,s),8.28(1H,d,J＝3.6Hz),8.23(2H,d,J＝8.0Hz),7.83(1H,d,J＝4.8Hz),7.38(2H,d,J＝8.0Hz),7.29(1H,t,J＝4.0Hz),2.67(3H,s),2.41(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):167.96,163.83,159.68,142.87,141.42,134.00,131.26,129.91,129.22,127.55,125.41,107.68,26.40,21.47；HRMS(ESI)m/z:Calcd for C16H14N2S[M+H]+:267.0950,Found:267.0945.
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in FIGS. 4-6.
Example 3:
compound (I)
Preparation of
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 4A molecular sieve (80-100 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of acetamidine hydrochloride 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 needle-shaped crystal product, wherein the yield is 87%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):8.48(1H,s),8.42(1H,s),8.31(1H,d,J＝8.0Hz),8.15(1H,d,J＝4.0Hz),7.77(1H,d,J＝8.0Hz),7.53(1H,t,J＝8.0Hz),7.43(1H,d,J＝4.0Hz),2.66(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):168.18,162.42,159.12,144.22,138.93,131.48,130.33,130.10,126.60,122.92,117.74,108.02,26.25；HRMS(ESI)m/z:Calcd for C15H10N2SBr2[M+H]+:408.9004,Found:408.9000.
the hydrogen spectrogram, carbon spectrogram and high-resolution mass spectrogram of the product are shown in FIGS. 7-9.
Example 4:
compound (I)
Preparation of
0.02mol of 4-methylacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of 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 4A molecular sieve (80-100 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of acetamidine hydrochloride 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 product, wherein the yield is 85%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):8.35(1H,s),8.22(2H,d,J＝8.0Hz),8.13(1H,d,J＝4.0Hz),7.42(1H,d,J＝4.0Hz),7.38(2H,d,J＝8.0Hz),2.66(3H,s),2.40(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):168.02,164.06,158.73,144.52,141.62,133.84,132.70,129.95,129.91,127.58,117.36,107.26,26.32,21.48；HRMS(ESI)m/z:Calcd for C16H13N2SBr[M+H]+:345.0056,Found:345.0046.
the hydrogen spectrum, carbon spectrum and high resolution mass spectrum of the product are shown in FIGS. 10-12.
Example 5:
compound (I)
Preparation of
0.02mol of 4-methoxyacetophenone was dissolved in 20mL of anhydrous ethanol, and 15mL of 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 4A molecular sieve (80-100 mesh) was added to the reaction mixture, and a mixed solution of 0.02mol of acetamidine hydrochloride 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 crystal product, wherein the yield is 84%. Spectral data for the product are as follows:
1H NMR(400MHz,DMSO-d6)δ(ppm):8.31(1H,s),8.29(2H,d,J＝8.8Hz),8.12(1H,d,J＝4.0Hz),7.42(1H,d,J＝4.0Hz),7.11(2H,d,J＝8.4Hz),3.87(3H,s),2.65(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):167.89,163.73,162.25,158.50,144.63,132.63,129.71,129.32,128.90,117.20,114.68,106.70,55.87,26.32；HRMS(ESI)m/z:Calcd for C16H13N2OSBr[M+H]+:361.0005,Found:361.0004.
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: three times in repetitionAverage value.
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)
1. A4- (2-thienyl) pyrimidine derivative, which has the following structural 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.
2. The process for producing a 4- (2-thienyl) pyrimidine derivative 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 5-bromothiophene-2-formaldehyde and anhydrous ethanol or a mixed solution of thiophene-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 is finished, adding a 4A molecular sieve into the reaction mixture, slowly dropping a mixed solution of acetamidine hydrochloride and 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 4A molecular sieve is 80-100 mesh.
4. Use of the 4- (2-thienyl) pyrimidine derivative according to claim 1 as an agricultural insecticide for killing one or more pests selected from the group consisting of elephant corn, clothes of corn and corn beetle.
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