CN109942561A - 4- (2- thienyl) pyrimidine derivatives and its preparation method and application - Google Patents
4- (2- thienyl) pyrimidine derivatives and its preparation method and application Download PDFInfo
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Abstract
The present invention provides a kind of 4- (2- thienyl) pyrimidine derivatives and its preparation method and application, general structure are as follows:R in general formula1For fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group, R2For hydrogen atom, chlorine atom, bromine atom, methyl.Thiphene ring is introduced into the molecular structure of pyrimidine by compound provided by the present application, has synthesized some 4- (2- thienyl) pyrimidine derivatives.Such compound structure is simple, has preferable toxic effect to storage pest, also there is preferable inhibitory activity to plant pathogenetic bacteria, will lay a good foundation for the initiative of novel pesticide.
Description
Technical field
The present invention relates to technical field of pesticide more particularly to a kind of 4- (2- thienyl) pyrimidine derivatives and preparation method thereof
And application.
Background technique
Pyrimidine is a kind of very important heterocyclic compound, is widely used in the fields such as medicine, pesticide, household chemicals.Greatly
Quantity research shows that such compound has preferable bioactivity, such as desinsection, sterilization, mite killing, weeding, plant growth regulating, resists
Virus, anticancer, anti-oxidant, anti-inflammatory etc..Since pyrimidines have efficiently, to people and animals' low toxicity, mode of action uniqueness, nocuousness
Biology is not likely to produce the advantages that drug resistance, and therefore, design, synthesis and the bioactivity research of molecular structure are heterocyclic compounds
Constantly there are structure novel, simple, the good compound appearance of bioactivity in a very active field in research.
Thiophene is a member important in heterocyclic compound, plays very important effect.The research of thiophene derivant is being cured
Also there is very main effect in medicine and chemistry of pesticide.Thiophene derivant has various bioactivity, for example, suppression
Bacterium, antiviral and antitumor, anti-inflammatory, desinsection and weeding etc..Meanwhile the compound containing thiphene ring usually all have efficiently, low toxicity,
To non-target organism safety, easy degradation, harmful organism do not allow the features such as being also easy to produce resistance, and constantly have structure in the environment
Compound that is novel, haveing excellent performance comes out.So during the research and development of pesticide, the compound containing thiphene ring will be by
To more extensive concern, become hot spot and the forward position of New pesticides discovery.
Up to the present, it yet there are no 4- (2- thienyl) pyrimidine derivatives to use as agricultural insecticide and fungicide
Report.
Summary of the invention
The purpose of the present invention is to provide a kind of new compounds and the chemical combination for being used as agricultural insecticide, fungicide
The preparation method of object.
A kind of 4- (2- thienyl) pyrimidine derivatives, general structure are as follows:
R in logical formula (I)1For fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group, R2It is former for hydrogen atom, chlorine
Son, bromine atom, methyl.
A kind of preparation method of 4- (2- thienyl) pyrimidine derivatives: substituted acetophenone is dissolved in dehydrated alcohol, then
10%NaOH solution is added thereto, under ice bath stirring, by the mixed liquor or thiophene of 5- bromothiophene -2- formaldehyde and dehydrated alcohol
The mixed liquor of pheno -2- formaldehyde and dehydrated alcohol is slowly instilled in above-mentioned mixed solution with constant pressure funnel, anti-at 0-5 DEG C
It answers, and whether is completed with thin layer silica gel plate inspection (TLC) reaction.After the reaction was completed, 4A molecular sieve is added into reaction mixture,
And the mixed solution of ethenylamidine hydrochloride and dehydrated alcohol is slowly instilled into mixture with constant pressure funnel, it is anti-at 40-50 DEG C
It answers, whether is completed with TLC detection reaction.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, with 10% hydrochloric acid solution
Adjust pH has Precipitation, filters, wash to neutrality, then is recrystallized with dehydrated alcohol to get the target compound is arrived.
Further, method as described above, the substituted acetophenone are 4- chloro-acetophenone, 4- bromoacetophenone, 4- methoxy
One of benzoylformaldoxime, 4- methyl acetophenone.
Further, method as described above, the 4A molecular sieve are 80-100 mesh.
A kind of application of 4- (2- thienyl) pyrimidine derivatives as agricultural insecticide or fungicide.
Further, application as described above, the pest that the insecticide is killed are sitophilus zea-mais, Gu Du and red flour beetle
It is one or more.
Further, application as described above, it is bacillary that the fungicide is able to suppress corn bacterial brown spot, rape
One of black spot, citrus bacterial canker disease, blakleg of potato, onion bulb rot disease, melon bacterial fruit blotch are a variety of.
The utility model has the advantages that
Thiphene ring is introduced into the molecular structure of pyrimidine by the present invention, has synthesized some 4- (2- thienyl) pyrimidine derivatives,
Such compound structure is simple, superior activity, will lay a good foundation for the initiative of novel pesticide.
The synthesis process of the compound of logical formula (I) is simple, and the method for using " treating different things alike ", i.e., be not by traditional method
Intermediate is separated to the reaction for carrying out next step again, but directly carries out the reaction of next step, which reduces operations
Step improves reaction efficiency, is beneficial to energy conservation consumption reduction.The compound of logical formula (I) to storage pest and plant pathogenetic bacteria all
There is preferable control efficiency, is had not been reported in the desinsection and fungicide being currently known.
Detailed description of the invention
Fig. 1 is the hydrogen spectrogram for the compound that embodiment 1 is prepared；
Fig. 2 is the carbon spectrogram for the compound that embodiment 1 is prepared；
Fig. 3 is the high resolution mass spectrum figure for the compound that embodiment 1 is prepared；
Fig. 4 is the hydrogen spectrogram for the compound that embodiment 2 is prepared；
Fig. 5 is the carbon spectrogram for the compound that embodiment 2 is prepared；
Fig. 6 is the high resolution mass spectrum figure for the compound that embodiment 2 is prepared；
Fig. 7 is the hydrogen spectrogram for the compound that embodiment 3 is prepared；
Fig. 8 is the carbon spectrogram for the compound that embodiment 3 is prepared；
Fig. 9 is the high resolution mass spectrum figure for the compound that embodiment 3 is prepared；
Figure 10 is the hydrogen spectrogram for the compound that embodiment 4 is prepared；
Figure 11 is the carbon spectrogram for the compound that embodiment 4 is prepared；
Figure 12 is the high resolution mass spectrum figure for the compound that embodiment 4 is prepared；
Figure 13 is the hydrogen spectrogram for the compound that embodiment 5 is prepared；
Figure 14 is the carbon spectrogram for the compound that embodiment 5 is prepared；
Figure 15 is the high resolution mass spectrum figure for the compound that embodiment 5 is prepared.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, the technical solution below in the present invention carries out clear
Chu is fully described by, it is clear that described embodiments are some of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
The present invention provides a kind of compound with desinsection and bacteriostatic activity, general structure is as follows:
R in logical formula (I)1For fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group, R2It is former for hydrogen atom, chlorine
Son, bromine atom, methyl.
General formula is the key reaction equation in the preparation of compounds of (I) are as follows:
R in formula1、R2Meaning be same as above.
The synthesis process of the compound of logical formula (I) is simple, and the method for using " treating different things alike ", i.e., be not by traditional method
Intermediate is separated to the reaction for carrying out next step again, but directly carries out the reaction of next step, which reduces operations
Step improves reaction efficiency, is beneficial to energy conservation consumption reduction.The compound of logical formula (I) to storage pest and plant pathogenetic bacteria all
There is preferable control efficiency, is had not been reported in the desinsection and fungicide being currently known.
Embodiment 1:
CompoundPreparation
0.02mol 4- chloro-acetophenone is dissolved in 20mL dehydrated alcohol, then addition 15mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol thiophene -2-formaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, 2 grams of 4A molecular sieves (80-100 mesh) are added into reaction mixture, and are slowly instilled into mixture with constant pressure funnel
Whether the mixed solution of 0.02mol ethenylamidine hydrochloride and 20mL dehydrated alcohol reacts at 40-50 DEG C, complete with TLC detection reaction
At.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, adjust pH to neutrality with 10% hydrochloric acid solution, there is precipitating to analyse
Out, it filters, washing, then is recrystallized with dehydrated alcohol to get white needle-like crystals product, yield 83% is arrived.The wave spectrum of product
Data 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.
Hydrogen spectrogram, carbon spectrogram, the high resolution mass spectrum figure of product are as shown in Figs. 1-3.
Embodiment 2:
CompoundPreparation
0.02mol 4- methyl acetophenone is dissolved in 20mL dehydrated alcohol, then addition 15mL10%NaOH is molten thereto
Liquid.Under ice bath stirring, slowly with constant pressure funnel by the mixed liquor of 0.02mol thiophene -2-formaldehyde and 20mL dehydrated alcohol
It instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction is completed
Afterwards, 2 grams of 4A molecular sieves (80-100 mesh) are added into reaction mixture, and are slowly instilled into mixture with constant pressure funnel
Whether the mixed solution of 0.02mol ethenylamidine hydrochloride and 20mL dehydrated alcohol reacts at 40-50 DEG C, complete with TLC detection reaction
At.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, adjust pH to neutrality with 10% hydrochloric acid solution, there is precipitating to analyse
Out, it filters, washing, then is recrystallized with dehydrated alcohol to get White crystalline product, yield 90% is arrived.The spectral data of product
It is 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.
Hydrogen spectrogram, carbon spectrogram, the high resolution mass spectrum figure of product are as Figure 4-Figure 6.
Embodiment 3:
CompoundPreparation
0.02mol 4- bromoacetophenone is dissolved in 20mL dehydrated alcohol, then addition 15mL 10%NaOH is molten thereto
Liquid.Under ice bath stirring, by the mixed liquor constant pressure funnel of 0.02mol 5- bromothiophene -2- formaldehyde and 20mL dehydrated alcohol
It slowly instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction
After the completion, 2 grams of 4A molecular sieves (80-100 mesh) are added into reaction mixture, and with constant pressure funnel slowly into mixture
The mixed solution for instilling 0.02mol ethenylamidine hydrochloride and 20mL dehydrated alcohol, reacts at 40-50 DEG C, whether detects reaction with TLC
It completes.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, adjust pH to neutrality with 10% hydrochloric acid solution, there is precipitating to analyse
Out, it filters, washing, then is recrystallized with dehydrated alcohol to get white needle-like crystals product, yield 87% is arrived.The wave spectrum of product
Data 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.
Hydrogen spectrogram, carbon spectrogram, the high resolution mass spectrum figure of product are as Figure 7-9.
Embodiment 4:
CompoundPreparation
0.02mol 4- methyl acetophenone is dissolved in 20mL dehydrated alcohol, then addition 15mL10%NaOH is molten thereto
Liquid.Under ice bath stirring, by the mixed liquor constant pressure funnel of 0.02mol 5- bromothiophene -2- formaldehyde and 20mL dehydrated alcohol
It slowly instills in above-mentioned mixed solution, is reacted at 0-5 DEG C, and check whether reaction is completed with thin layer silica gel plate (TLC).Reaction
After the completion, 2 grams of 4A molecular sieves (80-100 mesh) are added into reaction mixture, and with constant pressure funnel slowly into mixture
The mixed solution for instilling 0.02mol ethenylamidine hydrochloride and 20mL dehydrated alcohol, reacts at 40-50 DEG C, whether detects reaction with TLC
It completes.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, adjust pH to neutrality with 10% hydrochloric acid solution, there is precipitating to analyse
Out, it filters, washing, then is recrystallized with dehydrated alcohol to get pale yellow powder shape product, yield 85% is arrived.The wave spectrum of product
Data 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 spectrogram of product, carbon spectrogram, high resolution mass spectrum figure are as shown in figs. 10-12.
Embodiment 5:
CompoundPreparation
0.02mol 4- methoxyacetophenone is dissolved in 20mL dehydrated alcohol, then 15mL10%NaOH is added thereto
Solution.Under ice bath stirring, the mixed liquor of 0.02mol 5- bromothiophene -2- formaldehyde and 20mL dehydrated alcohol is leaked with constant pressure addition
Bucket slowly instills in above-mentioned mixed solution, reacts at 0-5 DEG C, and checks whether reaction is completed with thin layer silica gel plate (TLC).Instead
After the completion of answering, 2 grams of 4A molecular sieves (80-100 mesh) are added into reaction mixture, and with constant pressure funnel slowly to mixture
The middle mixed solution for instilling 0.02mol ethenylamidine hydrochloride and 20mL dehydrated alcohol, reacts at 40-50 DEG C, is with TLC detection reaction
No completion.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, adjust pH to neutrality with 10% hydrochloric acid solution, there is precipitating
It is precipitated, filters, washing, then recrystallized with dehydrated alcohol to get light yellow crystal product, yield 84% is arrived.The wave spectrum of product
Data 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 spectrogram of product, carbon spectrogram, high resolution mass spectrum figure are as illustrated in figs. 13-15.
Embodiment 6: the measurement of the compounds of this invention insecticidal activity
(1) test pest
Corundum Sitophilusspp. imago, Gu Du adult and red flour beetle adult, they are the indoor sensitive strain for many generations raised throughout the year.
(2) measuring method
Medicine method is mixed using feed: untested compound and wheatfeed are uniformly mixed by certain dosage.100 grams are weighed to mix
Medicine feed puts into test pest 30 into each bottle in 500mL wide-mouth bottle, wraps up bottleneck with calico, then place it in
Temperature is 28~30 DEG C, continues to raise in the insectary that relative humidity is 70~80%, while the feed not mix medicine is blank
Control.Death condition is recorded after 14 days, each experiment is repeated 3 times, and calculates corrected mortality with following equation:
(3) experimental result
The desinsection of the compounds of this invention the results are shown in Table 1.
Cytotoxicity of 1 the compounds of this invention of table to storage pest
a: duplicate average value three times.
There is preferable cytotoxicity to these pests from the compounds of this invention known to upper table 1.
Embodiment 7: the measurement of the compounds of this invention bacteriostatic activity
(1) test plant pathogenetic bacteria
Corn bacterial brown spot, rape bacterial black rot, citrus bacterial canker disease, blakleg of potato, onion bulb are rotten
Rotten disease, melon bacterial fruit blotch.
(2) measuring method
(a) activation of strain: beef extract-peptone culture medium slant, 37 DEG C of mistakes will be inoculated in for the bacterium bacterial strain of examination
Night culture.
(b) preparation of bacteria suspension: in the conical flask equipped with 100mL beef extract-peptone fluid nutrient medium, it is inoculated with a ring
The strains tested activated, in 37 DEG C of culture 18h, after obtaining initial bacteria suspension, then it is dilute using gradient with sterile saline
Interpretation of the law is made into debita spissitudo (106~107CFU/mL bacteria suspension) is spare.
(c) measurement of minimum inhibitory concentration (MIC): test compound is dissolved in dimethyl sulfoxide, then is spat with containing 0.1%
The sterile saline of temperature -80, the solution of various concentration is diluted to using doubling dilution, is uniformly mixed.After taking dilution
Sample solution 1mL, be added in sterilized 19mL culture medium, be uniformly mixed, plate is made.After culture medium solidification, use
It is 10 that above-mentioned concentration, which is added, in rubbing method6The 200 μ L of bacteria suspension of CFU/mL observes bacterial growth feelings in 37 DEG C of 16~18h of culture
Condition, using the concentration that integral asepsis is grown as the MIC value of test sample solution, meanwhile, with corresponding molten without test compound
Liquid is blank control.
(3) experimental result
The bacteriostatic activity of the compounds of this invention is shown in Table 2.
Inhibitory activity of 2 the compounds of this invention of table to plant pathogenetic bacteria
There is preferable inhibitory effect to these plant pathogenetic bacterias from the compounds of this invention known to upper table 2.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although
Present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: it still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features；
And these are modified or replaceed, technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution spirit and
Range.
Claims (7)
1. a kind of 4- (2- thienyl) pyrimidine derivatives, which is characterized in that its general structure is as follows:
R in logical formula (I)1For fluorine atom, chlorine atom, bromine atom, iodine atom, methyl, methoxyl group, R2For hydrogen atom, chlorine atom, bromine
Atom, methyl.
2. a kind of preparation method of 4- (2- thienyl) pyrimidine derivatives, it is characterised in that: be dissolved in substituted acetophenone anhydrous
In ethyl alcohol, then 10%NaOH solution is added thereto, under ice bath stirring, by the mixed of 5- bromothiophene -2- formaldehyde and dehydrated alcohol
The mixed liquor for closing liquid or thiophene -2-formaldehyde and dehydrated alcohol is slowly instilled in above-mentioned mixed solution with constant pressure funnel,
It reacts at 0-5 DEG C, and whether is completed with thin layer silica gel plate inspection reaction.After the reaction was completed, 4A points are added into reaction mixture
Son sieves, and slowly instills the mixed solution of ethenylamidine hydrochloride and dehydrated alcohol into mixture with constant pressure funnel, at 40-50 DEG C
Whether lower reaction is completed with TLC detection reaction.After the reaction was completed, it filters, a large amount of ice water is added into filtrate, with 10% hydrochloric acid
Solution adjusts pH to be had Precipitation, filters, wash to neutrality, then is recrystallized with dehydrated alcohol to get the target chemical combination is arrived
Object.
3. according to the method described in claim 2, it is characterized in that, the substituted acetophenone is 4- chloro-acetophenone, 4- bromobenzene second
One of ketone, 4- methoxyacetophenone, 4- methyl acetophenone.
4. according to the method described in claim 2, it is characterized in that, the 4A molecular sieve is 80-100 mesh.
5. a kind of application of 4- (2- thienyl) pyrimidine derivatives as agricultural insecticide or fungicide.
6. application according to claim 5, the pest that the insecticide is killed is in sitophilus zea-mais, Gu Du and red flour beetle
It is one or more.
7. application according to claim 5, it is bacillary black that the fungicide is able to suppress corn bacterial brown spot, rape
One of pinta, citrus bacterial canker disease, blakleg of potato, onion bulb rot disease, melon bacterial fruit blotch are a variety of.
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| CN111004208A (en) * | 2019-12-25 | 2020-04-14 | 西华大学 | 2-cyano-3-thiophene substituted valeramide derivative and application thereof |
| CN111004208B (en) * | 2019-12-25 | 2020-11-24 | 西华大学 | 2-cyano-3-thiophene substituted valeramide derivative and application thereof |
| CN113024528A (en) * | 2021-03-11 | 2021-06-25 | 西华大学 | 2- (2-thiophenecarboxamido) benzopyran compound and application thereof in pesticides |
| CN113024528B (en) * | 2021-03-11 | 2024-01-09 | 西华大学 | 2- (2-thiophenecarboxamido) benzopyran compounds and their use in pesticides |
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