CN112106780A - Application of harmine analog in prevention and treatment of agricultural plant diseases - Google Patents
Application of harmine analog in prevention and treatment of agricultural plant diseases Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Abstract
The invention discloses application of a camel alkaloid analogue W-1-W-19 in preparation of a compound for preventing and treating or resisting agricultural plant diseases. The antibacterial activity test result shows that the compound of the invention has better inhibition effect on sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum, pyricularia grisea and fusarium oxysporum 6 plant pathogenic fungi, wherein part of the compound has excellent inhibition activity on botrytis cinerea and can be developed as a bactericide.
Description
Technical Field
The invention belongs to the field of medicinal chemistry, discloses a new application of a camel alkaloid analogue, and particularly relates to an application of an analogue W-1-W-19 in preventing and treating plant diseases caused by sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum, pyricularia grisea and fusarium oxysporum.
Background
At present, chemical agents are mostly adopted to control plant fungal diseases in agricultural production, but the resistance growth speed is astonishing in the long-term single use process of the medicine. Benzimidazole, triazole and methoxy acrylate antibacterial agents which are honored as three milestones in the field of agricultural antibacterial agents face severe resistance problems at present. However, the demand of agricultural production for antibacterial drugs is increasing day by day, so the development of novel pesticides with high efficiency, low toxicity and low residue is one of the important tasks of pesticide creation at present. Plant-derived pesticides have become an important field of pesticide research and development gradually due to their advantages of low toxicity, no residue, high selectivity, easy decomposition, difficult generation of drug resistance and the like. Almost 50% or more of the pesticide chemical entities that are currently commercialized are derived from the inspiration conferred on natural products by random screening, biomimetic synthesis, bio-rational design or natural products. According to the statistical data published by Agranova2018 in 9 months, the proportion of natural products and bionic medicines derived from the natural products is close to 60% in the market composition of bactericide commodity medicines in 2016. Therefore, searching and screening potential antibacterial active ingredients from natural resources, especially plant resources, and performing optimization design by taking the potential antibacterial active ingredients as a lead structure are becoming one of the main research directions for creating novel bactericides. The fungal diseases account for more than 70 percent of plant diseases, according to statistics, the fungal diseases cause the reduction of yield of main crops in the world by about 10 percent each year, the economic loss reaches hundreds of billions of dollars, and the main grain and economic crops in China, such as rice, cotton and the like, also have serious fungal diseases. Therefore, we selected representative pathogenic fungi in both crops, pyricularia grisea and fusarium oxysporum, as our disease test subjects. In addition, we also selected 4 important plant pathogenic fungi sclerotinia sclerotiorum (, rhizoctonia solani, botrytis cinerea and fusarium graminearum) as subjects.
The camelinin A is a natural quinazoline alkaloid separated from Chinese herbal medicine Artemisia camelina (Peganum nigrostrum Bunge) in 1997, and has a chemical structure similar to that of camptothecin. The camelinine has been reported to have certain inhibitory effects on topoisomerase I and topoisomerase II ((1) J.Am.chem.Soc.,2003,125, 13628-. Preliminary studies (European Journal of Medicinal Chemistry,2020,194,112253) have found that camelinine derivatives exhibit a good inhibitory effect against agricultural pathogens such as rice blast, sclerotinia rot of colza and gray mold of tomato. According to the invention, the harmine A is used as a leading model, the split strategy is applied, the benzimidazole structure with the active functional group is embedded in the D ring of the harmine A, the harmine analogs with a brand-new structure are constructed, and the partially synthesized compound has a good antibacterial effect on Botrytis cinerea and Fusarium oxysporum and can be developed as a novel bactericide.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a new application of the harmine analog for agricultural production, namely the application of the harmine analog as a biological pesticide in preventing and treating plant diseases caused by sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum, pyricularia grisea and fusarium oxysporum.
In order to achieve the purpose, the invention provides the following technical method: a medicine for inhibiting the growth of sclerotinia sclerotiorum, rhizoctonia solani, botrytis cinerea, fusarium graminearum, pyricularia grisea and fusarium oxysporum contains camel alkaloid analogue represented by any one of compounds W-1-W-19 with a therapeutically effective dose, and the structure of the compound is shown in chemical formula 1.
Chemical formula 1
The invention relates to a method for preparing camelinine analog W-1-W-19 as introduced in chemical formula 2, which comprises the following steps:
chemical formula 2
The synthesis method of the harmine analogue is shown in the embodiment, a pure product is obtained by separation of conventional methods such as silica gel column chromatography for many times, and the harmine analogue W-1-W-19 of the claims is determined by spectrum technologies such as mass spectrum and nuclear magnetic resonance. Indoor biological activity determination results show that the camelinine analogue has a strong inhibition effect on sclerotinia sclerotiorum, botrytis cinerea, pyricularia grisea and fusarium oxysporum, and can be used for preparing bactericides.
Detailed Description
The foregoing and other aspects of the present invention will become more apparent from the following detailed description, given by way of example only, for purposes of illustrating the invention. This is not to be construed as limiting the invention. The experimental procedures described in the following examples are conventional unless otherwise specified.
EXAMPLE 1 Synthesis of target Compound W-1
The synthesis method of the compound W-1 is carried out according to the following reaction formula:
first step synthesis of intermediate 1: adding 28mmol of sodium metal into 16mL of ethanol under the condition of dry ice bath, and magnetically stirring until the sodium metal is dissolved to obtain a sodium ethoxide solution. Adding 15mmol of o-phenylenediamine and 18mmol of 2, 2-diethoxy ethyl acetate into a sodium ethoxide solution, refluxing for 24h, cooling to room temperature, spin-drying, dissolving the residue in water, adjusting the pH value with glacial acetic acid until precipitation is generated, adding ethyl acetate for extraction for 3 times, drying with anhydrous sodium sulfate, carrying out vacuum spin-drying on the solvent, carrying out column chromatography purification, eluting with petroleum ether and ethyl acetate (ratio 5:1), and spin-drying to obtain a white flocculent solid, namely an intermediate 1.
Second step synthesis of intermediate 2: adding 13.5mmol of sodium hydride into 120mL of tetrahydrofuran solution for a few times, adding 9mmol of 2- (diethoxymethyl) -1H-benzimidazole, refluxing for 30min, then adding 13.5mmol of 3-bromopropyne, refluxing for 8H, monitoring the reaction by TLC, cooling to room temperature after the reaction is completed, adding 60mL of water to quench the reaction, extracting for three times by using ethyl acetate, combining organic phases, drying by using anhydrous magnesium sulfate, decompressing, spin-drying, removing the solvent, obtaining red oily liquid, namely the intermediate 2, and directly putting the red oily liquid into the next step without purification.
Step three, synthesis of an intermediate 3: intermediate 2 was dissolved in 30mL THF solution, added to 15mL 12% HCl solution, refluxed for 24h, and after the reaction was complete, neutralized with saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, spin-dried under reduced pressure, purified by column chromatography, and eluted with petroleum ether and ethyl acetate (ratio 5:1) to give intermediate 3 as a yellow solid.
And step four, synthesizing a target compound W-1: adding 1mmol of intermediate 3 and 1mmol of aniline into a 50mL round-bottom flask, adding an appropriate amount of 1, 2-dichloroethane, stirring for 5 minutes, adding an appropriate amount of powdery 4A molecular sieve, adding 5mmol of boron trifluoride diethyl etherate under the protection of nitrogen, reacting for 24 hours at 80 ℃, cooling to room temperature after the reaction is finished, performing vacuum drying on the solvent, adding hot ethyl acetate for dissolving, filtering while hot, taking an organic phase, performing spin drying, performing column chromatography purification, and eluting by using dichloromethane and methanol solution (the ratio is 500:3 to 100:1) to obtain the intermediate (the synthetic method is shown in a literature: European Journal of Medicinal Chemistry 138(2017) 932-).
Yield: 35.3 percent; a tan powdered solid;1H NMR(400MHz,DMSO-d6):8.68(s,1H),8.21(d,J＝8.4Hz,1H),8.12(d,J＝8.2Hz,1H),7.90–7.83(m,2H),7.78(d,J＝7.8Hz,1H),7.73(d,J＝7.3Hz,1H),7.39(t,J＝7.4Hz,1H),7.33(t,J＝7.8Hz,1H),5.51(s,2H).MS-ESI m/z:calcd for C17H11N3:258.1[M+H]+.
example 2 Synthesis of target Compound W-2
The synthesis was carried out in the same manner as in example 1, except that aniline was replaced by 4-fluoroaniline.
Yield: 45.8 percent; a pale yellow powdery solid;1H NMR(400MHz,DMSO-d6):8.68(s,1H),8.21(d,J＝8.4Hz,1H),8.12(d,J＝8.2Hz,1H),7.90–7.83(m,2H),7.78(d,J＝7.8Hz,1H),7.73(d,J＝7.3Hz,1H),7.39(t,J＝7.4Hz,1H),7.33(t,J＝7.8Hz,1H),5.51(s,2H).MS-ESI m/z:calcd for C17H10N3F:276.06[M+H]+.
example 3 Synthesis of target Compound W-3
The synthesis was carried out in the same manner as in example 1, except that 4-chloroaniline was used instead of aniline.
Yield: 35.2 percent; a tan powdered solid;1H NMR(400MHz,DMSO-d6):8.71(s,1H),8.31(s,1H),8.24(d,J＝9.0Hz,1H),7.94–7.84(m,3H),7.47(t,J＝7.6Hz,1H),7.42(t,J＝7.5Hz,1H),5.58(s,2H).MS-ESI m/z:calcd for C17H10ClN3:292.04[M+H]+.
example 4 Synthesis of target Compound W-4
The synthesis was carried out as in example 1, except that 4-trifluoromethylaniline was used instead of aniline.
Yield: 38.7 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.91(s,1H),8.68(s,1H),8.41(d,J＝8.8Hz,1H),8.13(d,J＝8.9Hz,1H),7.92–7.83(m,2H),7.47(t,J＝7.3Hz,1H),7.41(t,J＝7.6Hz,1H),5.61(s,2H).MS-ESI m/z:calcd for C18H10N3F3:326.05[M+H]+.
EXAMPLE 5 Synthesis of the object Compound W-5
The synthesis was carried out in the same manner as in example 1, except that 4-methoxyaniline was used instead of aniline.
Yield: 47.4%; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.55(s,1H),8.11(d,J＝8.8Hz,1H),7.81(d,J＝8.0Hz,1H),7.74(d,J＝7.8Hz,1H),7.55–7.48(m,2H),7.40–7.29(m,2H),5.48(s,2H),3.96(s,3H).MS-ESI m/z:calcd for C18H13N3O:288.08[M+H]+.
example 6 Synthesis of the object Compound W-6
The synthesis was carried out in the same manner as in example 1, except that aniline was replaced by 3-fluoroaniline.
Yield: 38.2 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.73(s,1H),8.23(t,J＝7.8Hz,1H),7.97(d,J＝10.4Hz,1H),7.85(d,J＝8.0Hz,1H),7.78(d,J＝7.8Hz,1H),7.66(t,J＝9.2Hz,1H),7.44–7.31(m,2H),5.51(d,J＝9.9Hz,2H).MS-ESI m/z:calcd for C17H10N3F:276.05[M+H]+.
example 7 Synthesis of target Compound W-7
The synthesis was the same as in example 1, except that aniline was replaced by 2-fluoroaniline.
Yield: 41.4 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.76(s,1H),8.00–7.93(m,1H),7.86(d,J＝7.9Hz,1H),7.79(d,J＝7.8Hz,1H),7.74–7.67(m,2H),7.43–7.31(m,2H),5.53(s,2H).MS-ESI m/z:calcd for C17H10N3F:276.07[M+H]+.
example 8 Synthesis of the object Compound W-8
The synthesis was carried out in the same manner as in example 1 except that 4-fluorophenylenediamine was used instead of o-phenylenediamine.
Yield: 25.8 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.69(s,1H),8.21(d,J＝8.5Hz,1H),8.12(d,J＝8.1Hz,1H),7.91–7.77(m,2H),7.76–7.61(m,2H),7.32–7.14(m,1H),5.49(d,J＝13.0Hz,2H).MS-ESI m/z:calcd for C17H10N3F:276.06[M+H]+.
example 9 Synthesis of the object Compound W-9
The synthesis was carried out in the same manner as in example 1 except that 4, 5-difluorobenzene-1, 2-diamine was used in place of o-phenylenediamine.
Yield: 28.4 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.70(s,1H),8.02–7.91(m,1H),7.90–7.80(m,2H),7.74(d,J＝7.6Hz,1H),7.50–7.43(m,2H),5.48(s,2H).MS-ESI m/z:calcd for C17H9N3F2:294.06[M+H]+.
example 10 Synthesis of target Compound W-10
The synthesis was carried out in the same manner as in example 1 except that 4-nitrophthaldiamine was used instead of o-phenylenediamine.
Yield: 17.4 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.88(s,1H),8.78(d,J＝8.6Hz,1H),8.24(t,J＝9.9Hz,1H),8.16(d,J＝7.8Hz,1H),8.03(d,J＝8.9Hz,1H),7.94–7.88(m,1H),7.81–7.72(m,2H),5.63(d,J＝8.6Hz,2H).MS-ESI m/z:calcd for C17H10N4O2:325.36[M+Na]+.
example 11 Synthesis of the object Compound W-11
The synthesis was the same as in example 1, except that 3, 5-difluoroaniline was used instead of aniline.
Yield: 34.1 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.83(s,1H),7.92–7.84(m,2H),7.81(d,J＝7.9Hz,1H),7.72(t,J＝10.0Hz,1H),7.43–7.32(m,2H),5.51(s,2H).MS-ESI m/z:calcd for C17H9N3F2:294.1[M+H]+.
EXAMPLE 12 Synthesis of the object Compound W-12
The synthesis method is the same as example 1, only 4-fluoroaniline is used to replace aniline, and 4-fluorophenylenediamine is used to replace o-phenylenediamine.
Yield: 28.9 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.66(s,1H),8.27(t,J＝7.1Hz,1H),7.94(d,J＝9.3Hz,1H),7.89–7.74(m,2H),7.66(t,J＝10.6Hz,1H),7.32–7.14(m,1H),5.49(d,J＝13.1Hz,2H).MS-ESI m/z:calcd for C17H9N3F2:294.04[M+H]+.
example 13 Synthesis of the object Compound W-13
The synthesis procedure was the same as in example 1, except that aniline was replaced with 4-fluoroaniline and o-phenylenediamine was replaced with 4, 5-difluorobenzene-1, 2-diamine.
Yield: 28.6 percent(ii) a A yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.68(s,1H),8.33–8.22(m,1H),8.02–7.87(m,2H),7.57–7.48(m,2H),5.48(s,2H).MS-ESI m/z:calcd for C17H8N3F3:334.11[M+Na]+.
example 14 Synthesis of target Compound W-14
The synthesis was carried out in the same manner as in example 1 except that 4- (trifluoromethoxy) benzene-1, 2-diamine was used instead of o-phenylenediamine.
Yield: 23.2 percent; a brown powdery solid;1H NMR(400MHz,DMSO-d6):8.72(s,1H),8.22(d,J＝8.0Hz,1H),8.13(d,J＝6.7Hz,1H),7.98–7.82(m,2H),7.82–7.69(m,2H),7.37(d,J＝33.3Hz,1H),5.53(d,J＝5.3Hz,2H).MS-ESI m/z:calcd for C18H10N3F3O:342.14[M+H]+.
example 15 Synthesis of the target Compound W-15
The synthesis was carried out in the same manner as in example 1 except that o-phenylenediamine was replaced with 2, 3-diaminofluorobenzene.
Yield: 32.7 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.69(s,1H),8.22(d,J＝8.5Hz,1H),8.13(d,J＝7.9Hz,1H),7.88(t,J＝7.7Hz,1H),7.73(t,J＝7.5Hz,1H),7.65(dd,J＝23.1,8.1Hz,1H),7.41–7.11(m,2H),5.58(d,J＝46.1Hz,2H).MS-ESI m/z:calcd for C17H10N3F:276.03[M+H]+.
EXAMPLE 16 Synthesis of the Compound of interest W-16
The synthesis was carried out in the same manner as in example 1, except that 3, 4-diaminobenzonitrile was used instead of o-phenylenediamine.
Yield: 35.9 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.74(s,1H),8.42(d,J＝13.9Hz,1H),8.23(d,J＝8.5Hz,1H),8.14(d,J＝8.2Hz,1H),8.00(t,J＝7.2Hz,1H),7.90(t,J＝7.7Hz,1H),7.80–7.73(m,2H),5.56(d,J＝7.5Hz,2H).MS-ESI m/z:calcd for C18H10N4:283.07[M+H]+.
example 17 Synthesis of the object Compound W-17
The synthesis was carried out in the same manner as in example 1 except that o-phenylenediamine was replaced by 4-methoxy-o-phenylenediamine.
Yield: 48.5 percent; a yellow powdered solid;1H NMR(400MHz,DMSO-d6):8.62(s,1H),8.21–8.14(m,1H),8.08(d,J＝8.0Hz,1H),7.84(t,J＝7.7Hz,1H),7.74–7.62(m,2H),7.32(dd,J＝13.4,2.4Hz,1H),7.04–6.90(m,1H),5.42(d,J＝8.3Hz,2H),3.86(d,J＝7.2Hz,3H).MS-ESI m/z:calcd for C18H13N3O:288.04[M+H]+.
EXAMPLE 18 Synthesis of the object Compound W-18
The synthesis was carried out in the same manner as in example 1 except that 4-chloro-1, 2-phenylenediamine was used instead of o-phenylenediamine.
Yield: 27.5 percent; a brown powdery solid;1H NMR(400MHz,DMSO-d6):8.70(s,1H),8.21(d,J＝8.5Hz,1H),8.17–8.09(m,1H),7.98–7.80(m,3H),7.72(d,J＝12.8Hz,1H),7.38(d,J＝8.8Hz,1H),5.51(d,J＝10.7Hz,2H).MS-ESI m/z:calcd for C17H10N3Cl:292.02[M+H]+.
EXAMPLE 19 Synthesis of the Compound of interest W-19
The synthesis was carried out in the same manner as in example 1 except that 4-bromoo-phenylenediamine was used instead of o-phenylenediamine.
Yield: 26.5 percent; a brown powdery solid;1H NMR(400MHz,DMSO-d6):8.70(s,1H),8.21(d,J＝8.6Hz,1H),8.13(d,J＝8.4Hz,1H),8.07(d,J＝19.4Hz,1H),7.88(t,J＝7.6Hz,1H),7.82–7.76(m,1H),7.73(t,J＝7.5Hz,1H),7.57–7.42(m,1H),5.50(d,J＝11.1Hz,2H).MS-ESI m/z:calcd for C17H10N3Br:336.11[M+H]+.
example 20 method of testing anti-phytopathogenic fungi Activity of Compounds W-1 to W-19 and the results
The antibacterial activity assay of the present invention was performed using a potato dextrose agar medium (PDA medium). The preparation method comprises the following steps: firstly, washing and peeling potatoes, weighing 200g of potatoes, cutting the potatoes into small pieces, adding water, boiling the small pieces thoroughly (the potato pieces can be torn by a glass rod after boiling for 20-30 minutes), filtering the small pieces with eight layers of gauze, heating, adding 15g of agar, continuously heating, stirring uniformly, adding 20g of glucose after the agar is dissolved, stirring uniformly, slightly cooling, supplementing water to 1000 ml, subpackaging the obtained product in conical bottles, plugging and binding, and sterilizing at 121 ℃ for 2 hours for later use. Respectively dissolving the compounds W-1 to W-19 in DMSO, adding the dissolved compounds into a culture medium, uniformly mixing to ensure that the concentrations of the compounds in the culture medium are respectively 50 mu g/mL, taking DMSO with equal concentration as a blank control, and taking the azoxystrobin which is a commercial drug as a positive control. And (3) pouring the plates, cooling, inoculating bacteria respectively, culturing in an incubator at 23 ℃, and determining the bacteriostasis rate of each compound by taking blank control hypha to overgrow the culture dish as a limit. All experiments were performed in triplicate or in triplicate. The calculation of the bacteriostasis rate is carried out according to the following calculation formula:
anti-plant diseases of compounds W-1 to W-19The results of the original bacteria activity test are shown in Table 1. Partial compounds have obvious inhibiting effect on botrytis cinerea, so that partial compounds are selected to be tested in a concentration reduction mode and EC of the partial compounds is obtained50The test results are shown in Table 2.
TABLE 1 anti-phytopathogen Activity test data for target Compounds W-1 to W-19
TABLE 2 EC against Botrytis cinerea for part of the compounds50Value of
As shown in the results of antibacterial activity determination in Table 1, the camelinine analogs W-1-W-19 prepared by the invention show different inhibitory activities to 6 plant pathogenic bacteria when the concentration is 50ppm, wherein most compounds show excellent inhibitory activity to botrytis cinerea, and in addition, part of compounds also show better inhibitory action to fusarium oxysporum. As can be seen from the data in Table 2, the EC of most compounds against Botrytis cinerea in the in vitro antifungal activity test experiment50The EC of W-7, W-8, W-10, W-12, W-15 on Botrytis cinerea with a value of less than 0.5 μ g/mL50The activity is more prominent when the value is about 0.04 mu g/mL. The camel alkaloid derivative has a simple structure, easily obtained raw materials and further research and development values, and is expected to be developed into a novel bactericide, so that the compound can be used for preparing the bactericide.
Claims (8)
1. The invention relates to application of a camel alkaloid analogue in preparation of a medicine for preventing and treating or resisting agricultural diseases, and belongs to new application of the camel alkaloid analogue.
2. The camelinine analogues W-1-W-19 according to claim 1 have the following molecular structural features:
3. the application of the camelinine analog W-1-W-19 in the preparation of the drug for preventing and treating diseases caused by sclerotinia sclerotiorum according to the claim 1.
4. The application of the camelinine analog W-1-W-19 in the preparation of drugs for preventing or treating Rhizoctonia solani according to claim 1.
5. The application of the camelinine analog W-1-W-19 in the preparation of drugs for preventing or treating botrytis cinerea according to claim 1.
6. The use of a camelinine analogue W-1-W-19 according to claim 1 in the preparation of a medicament for the control or resistance of a disease caused by Fusarium graminearum.
7. The application of the camelinine analog W-1-W-19 in the preparation of the drugs for preventing or treating the botrytis cinerea according to claim 1.
8. The application of the camelinine analog W-1-W-19 in the preparation of the drugs for preventing or treating fusarium oxysporum according to claim 1.
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