CN113045474A - Application of alkaloid arnodine and derivatives thereof in preventing and treating plant virus and bacterial diseases - Google Patents
Application of alkaloid arnodine and derivatives thereof in preventing and treating plant virus and bacterial diseases Download PDFInfo
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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Abstract
The invention relates to an application of alkaloid arnodine and derivatives thereof in treating plant virus pathogens, and the invention discovers for the first time that the arnodine and the derivatives I-1 to I-25 thereof show good plant virus pathogen resistance activity, and can well inhibit Tobacco Mosaic Virus (TMV) and cucumber fusarium wilt, peanut brown spots, apple ring spots, wheat sharp shells, corn small spots, watermelon anthracnose, rice bakanae, tomato early blight, wheat scab, rice blast, phytophthora capsici, sclerotium napellum, cucumber botrytis cinerea and 14 plant pathogens of rice sharp shells.
Description
Technical Field
The invention relates to an application of alkaloid arnodine and derivatives thereof in preventing and treating plant viruses and pathogenic bacteria, belonging to the technical field of agricultural protection.
Background
Plant viruses (viruses of plants) are viruses that infect eukaryotes such as higher plants and algae. Because of the particularity of the plant virus in the aspects of structure, physiology and biochemistry, human does not find an anti-plant virus agent with high efficiency and low toxicity, so that the generation area of the plant virus disease tends to be continuously enlarged, and the increase of the income of farmers and the improvement of the benefit are seriously influenced. Plant viruses are not only of a wide variety but also widely distributed, and virus diseases are the second largest plant diseases next to fungal diseases in agricultural production. Since the virus is absolutely parasitic in plant cells, the substances, energy and place required for the replication of the virus are completely dependent on the host, and the plants do not have the complete advanced immune metabolic system (science, 2014, 344 (6181): 299-303) like animals), so that the control of plant virus diseases is particularly difficult, and the element is called plant cancer.
At present, not only are few effective plant virus inhibitors available, but also fewer therapeutic agents are available, and the control effect of the reported agents in actual field application is mostly below 60%. Representative registered varieties of pesticides currently in use are: amino-oligosaccharin (oligosaccharide natural product with D-glucosamine linked by beta-1.4 glycosidic bond), ningnanmycin, ribavirin, and virus A (moroxydine hydrochloride, copper acetate).
The biogenic natural pesticide mainly refers to pesticide developed by secondary metabolite with agricultural biological activity generated by plants, animals, microorganisms and the like, such as 2.5% rotenone emulsifiable concentrate, 15% jinggangmycin water soluble powder and the like. Secondary metabolites were first extracted by Czapek in the 20 th century. The so-called secondary metabolites, whose origin and nature are different from the basic metabolites such as nucleic acid proteins and the like, are the final products of complex branched metabolic pathways, and most are not directly involved in maintaining the primary biochemical processes involved in the growth and development and reproduction of the producers. Discovery of new pesticides based on natural products has gradually become the main route to innovative pesticides.
Arundine (structural formula I) is a natural alkaloid with a bisindole structure, and belongs to one of bisindole methane natural products. In 1994, Khuzhaev et al first isolated arnadine from the root system of arundo donax (chem. nat. comp., 1994, 30, 635). Later, researchers also classified this natural product among the metabolites of marine bacteria (J.Nat.Prod., 2003, 66, 1520; Tetrahedron Lett., 2017, 58, 3172). Biological activity researches find that the arnodine has good anti-tumor activity (Cancer Res, 2006, 66, 4952; Cancer Lett, 2008, 269, 326), and no report about the anti-plant virus pathogen activity of the compound exists at present.
Disclosure of Invention
The invention provides an application of alkaloid arnodine and a derivative I thereof in preventing and treating plant virus and bacterial diseases. The alkaloid arnodine and the derivative I thereof have good activity of resisting plant viruses and germs.
The alkaloid arnodine and the derivatives thereof are shown as a general formula I, and are specifically I-1 to I-25.
Structural formula I
The alkaloid arnodine and derivatives I-1-I-25 thereof are prepared according to a method shown in a reaction formula I, and two equivalents of corresponding indole and one equivalent of corresponding aldehyde or ketone are condensed under the catalysis of 0.2 equivalent of iodine to obtain compounds I-1-I-25.
Reaction formula one
Compared with the prior art, the invention discovers for the first time that the arnodine alkaloid and the derivatives I-1 to I-25 thereof show good plant virus and germ resisting activity, and can well inhibit Tobacco Mosaic Virus (TMV) and cucumber fusarium wilt, peanut brown spots, apple ring rot, wheat sharp blight, corn small spots, watermelon anthracnose, rice bakanae, tomato early blight, wheat scab, rice blast, phytophthora capsici, rape sclerotium, cucumber gray mold and 14 plant germs of rice sharp blight.
Detailed Description
Example 1: synthesis of Compounds I-1 to I-25: to a solution of the corresponding indole (5mmol) and the corresponding aldehyde or ketone (2.5mmol) in acetonitrile (25mL) at 0 ℃ under stirring was added I2(0.5 mmol). Stirring at this temperature for 30min, adding 5% Na2S2O3The reaction was quenched with solution (20 mL). Reaction solutionExtracted with ethyl acetate (3X 50mL), and the organic phase was washed with saturated brine (100mL) and anhydrous Na2SO4Drying, filtering and concentrating. And performing column chromatography on the residue by using petroleum ether and ethyl acetate (5: 1, v/v) to obtain compounds I-1 to I-25.
Bis (1H-indol-3-yl) methane (I-1, arenidine) as a pink solid; the yield thereof was found to be 61%; melting point 161-163 ℃;1H NMR (400MHz，DMSO-d6)δ10.72(s，2H)，7.52(d，J＝7.9Hz，2H)，7.31(d，J＝8.1Hz，2H)，7.13(s， 2H)，7.05-6.99(m，2H)，6.94-6.88(m，2H)，4.12(s，2H)；13C NMR(100MHz，DMSO-d6)δ 136.4，127.2，122.7，120.7，118.6，118.0，114.2，111.3，20.9.C17H15N2[M+H]+247.1230，found (ESI+)247.1235.
bis (5-bromo-1H-indol-3-yl) methane (I-2), a pink solid; the yield is 53 percent; melting point 172-;1H NMR(400MHz， CDCl3)δ7.99(s，2H)，7.73(s，2H)，7.31-7.24(m，4H)，6.96(s，2H)，4.16(s，2H)；13C NMR(100 MHz，CDCl3)δ135.1，129.2，124.9，123.4，121.8，114.9，112.6，21.1.C17H13Br2N2[M+H]+ 402.9440，found(ESI+)402.9443.
bis (5-methoxy-1H-indol-3-yl) methane (I-3), a pink solid; the yield is 49%; melting point 169-170 ℃;1H NMR(400 MHz，DMSO-d6)δ10.56(s，2H)，7.21(d，J＝8.7Hz，2H)，7.08(s，2H)，7.01(s，2H)，6.69(dd，J＝ 8.7，2.4Hz，2H)，4.05(s，2H)，3.70(s，3H)；13C NMR(100MHz，DMSO-d6)δ152.7，131.5，127.5， 123.4，113.9，111.9，110.7，100.7，55.3，20.8.C19H19N2O2[M+H]+307.1441，found(ESI+) 307.1448.
bis (6-bromo-1H-indol-3-yl) methane (I-4), a pink solid; the yield thereof was found to be 61%; melting point 206-;1H NMR(400MHz， DMSO-d6)δ10.92(s，2H)，7.50(d，J＝1.3Hz，2H)，7.43(d，J＝8.4Hz，2H)，7.18(s，2H)，7.04(dd， J＝8.4，1.5Hz，2H)，4.10(s，2H)；13C NMR(100MHz，DMSO-d6)δ137.2，126.1，123.9，120.9， 120.3，114.2，113.8，113.6，20.6.C17H13Br2N2[M+H]+402.9440，found(ESI+)402.9444.
3, 3' - (propyl-2, 2-disubstituted) bis (5-bromo-1H-indole) (I-5.) brown oil; the yield is 68 percent;1H NMR(400MHz， CDCl3)δ7.95(s，2H)，7.44(s，2H)，7.14(s，4H)，7.05(d，J＝2.1Hz，2H)，1.83(s，6H)；13C NMR (100MHz，CDCl3)δ135.8，127.9，124.8，124.4，123.3，121.7，112.7，112.1，34.6，29.8.C19H17Br2N2 [M+H]+430.9753，found(ESI+)430.9757.
3, 3' - (butyl-1, 1-disubstituted) bis (5-bromo-1H-indole) (I-6). brown oil; the yield is 74 percent;1H NMR(400MHz， CDCl3)δ7.96(s，2H)，7.66(d，J＝1.7Hz，2H)，7.17-7.24(m，4H)，7.01(d，J＝2.2Hz，2H)，4.34(t， J＝7.5Hz，1H)，2.11-2.18(m，2H)，1.36-1.42(m，2H)，0.96(t，J＝7.3Hz，3H)；13C NMR(100 MHz，CDCl3)δ135.3，128.7，124.7，122.7，122.1，119.6，112.7，112.4，37.5，33.7，21.4，14.2. C20H19Br2N2[M+H]+444.9910，found(ESI+)444.9906.
3, 3' - (butyl-2, 2-disubstituted) bis (5-bromo-1H-indole) (I-7). brown oil; the yield is 71%;1H NMR(400MHz， CDCl3)δ8.04(s，2H)，7.42(s，2H)，7.29-7.15(m，6H)，2.37(q，J＝7.4Hz，2H)，1.77(s，3H)，0.76 (t，J＝7.3Hz，3H)；13C NMR(100MHz，CDCl3)δ135.7，128.0，124.4，123.5，123.4，122.4，112.6， 112.0，38.3，32.5，26.0，8.9.C20H19Br2N2[M+H]+444.9910，found(ESI+)444.9914.
3, 3' - (2-methylpropyl-1, 1-disubstituted) bis (5-bromo-1H-indole) (I-8)(ii) a The yield is 59 percent; melting point 140-;1H NMR(400MHz，CDCl3)δ7.86(s，2H)，7.71(s，2H)，7.17-7.25(m，2H)，7.11(d，J＝8.6Hz， 2H)，7.04(d，J＝1.55Hz，2H)，4.02(d，J＝8.9Hz，1H)，2.54-2.59(m，1H)，0.95(d，J＝6.5Hz， 6H)；13C NMR(100MHz，CDCl3)δ134.9，129.1，124.6，122.9，122.1，118.9，112.6，112.4，41.4， 32.5，21.9.C20H19Br2N2[M+H]+444.9910，found(ESI+)444.9907.
3, 3' - (cyclohexylmethine) bis (5-bromo-1H-indole) (I-9.) brown oil; the yield is 43 percent;1H NMR(400MHz， CDCl3)δ7.95(s，2H)，7.73(s，2H)，7.12-7.21(m，4H)，7.07(d，J＝1.41Hz，2H)，4.07(d，J＝9.23 Hz，1H)，2.13-2.22(m，1H)，1.65-1.77(m，6H)，0.96-1.19(m，4H)；13C NMR(100MHz，CDCl3)δ 134.9，129.2，124.6，122.8，122.0，118.8，112.6，112.4，42.4，40.3，32.4，26.6.C23H23Br2N2[M+H]+ 485.0223，found(ESI+)485.0227.
3, 3' - (octyl-1, 1-disubstituted) bis (5-bromo-1H-indole) (I-10). brown oil; the yield is 57%;1H NMR(400MHz， CDCl3)δ7.90(s，2H)，7.65(s，2H)，7.14-7.24(m，4H)，6.97(d，J＝2.0Hz，2H)，4.29(t，J＝7.5Hz， 1H)，2.10-2.16(m，2H)，1.22-1.33(m，10H)，0.85(t，J＝6.5Hz，3H)；13C NMR(100MHz，CDCl3) δ135.3，128.7，124.7，122.7，122.1，119.7，112.7，112.4，35.3，34.0，31.9，29.6，29.3，28.2，22.7，14.2. C24H27Br2N2[M+H]+501.0536，found(ESI+)501.0541.
3, 3' - (phenylmethylidene) bis (1H-indole) (I-11.) red solid; the yield is 86%; melting point 146-;1H NMR(400 MHz，CDCl3)δ7.81(s，2H，NH)，7.38(d，J＝7.9Hz，2H，Ar-H)，7.31-7.34(m，4H，Ar-H)， 7.20-7.28(m，3H，Ar-H)，7.17-7.14(m，2H，Ar-H)，6.97-7.01(m，2H，Ar-H)，6.60(d，J＝1.5Hz， 2H，Ar-H)，5.87(s，1H，Ar-CH)；13C NMR(100MHz，CDCl3)δ144.0，136.7，128.8，128.3，127.1， 126.2，123.6，121.9，120.0，119.7，119.3，111.1，40.2.C23H19N2[M+H]+323.1543，found(ESI+) 323.1540.
3, 3' - (phenylmethylidene) bis (5-bromo-1H-indole) (I-12.) a red solid; the yield is 88%; melting point 249-251 ℃;1H NMR (400MHz，CDCl3)δ8.01(s，2H，NH)，7.50(s，2H，Ar-H)，7.32-7.33(m，3H，Ar-H)，7.29(s，2H，Ar-H)，7.26-7.28(m，3H，Ar-H)，6.67(d，J＝1.9Hz，2H，Ar-H)，5.78(s，1H，Ar-CH)；13C NMR (100MHz，DMSO-d6)δ144.3，135.2，128.4，128.2，126.0，125.2，123.4，121.2，117.6，113.6，110.9， 38.9.C23H17Br2N2[M+H]+478.9753，found(ESI+)478.9751.
3, 3' - (phenylmethylidene) bis (5-methoxy-1H-indole) (I-13.) a red solid; the yield is 81%; melting point 224-;1H NMR(400MHz，CDCl3)δ8.01(s，2H，NH)，7.50(s，2H，Ar-H)，7.32-7.33(m，3H，Ar-H)，7.29(s，2H，Ar-H)，7.26-7.28(m，3H，Ar-H)，6.67(d，J＝1.9Hz，2H，Ar-H)，5.78(s，1H，Ar-CH)；13C NMR (100MHz，DMSO-d6)δ144.3，135.2，128.4，128.2，126.0，125.2，123.4，121.2，117.6，113.6，110.9， 38.9.C25H23N2O2[M+H]+383.1754，found(ESI+)383.1758.
3, 3' - ((4-methoxyphenyl) methine) bis (5-bromo-1H-indole) (I-14.) red solid; the yield is 92 percent; melting point 220-222 ℃;1H NMR(400MHz，CDCl3)δ8.03(s，2H，NH)，7.50(d，J＝1.3Hz，2H，Ar-H)，7.28(s，1H，Ar-H)， 7.26(s，1H，Ar-H)，7.20-7.24(m，4H，Ar-H)，6.85(d，J＝8.6Hz，2H，Ar-H)，6.62(d，J＝1.5Hz，2H， Ar-H)，5.72(s，1H，Ar-CH)，3.82(s，3H，OCH3)；13C NMR(100MHz，DMSO-d6)δ157.4，136.2， 135.2，129.1，128.3，125.1，123.4，121.2，118.0，113.5，110.8，54.9，38.0.C24H19Br2N2O[M+H]+ 508.9859，found(ESI+)508.9867.
4- (bis (5-bromo-1H-indol-3-yl) methyl) phenol (I-15) as a pink solid; the yield is 76%; melting point 166-167 ℃;1H NMR (400MHz，CDCl3)δ7.95(s，2H)，7.48(s，2H)，7.17-7.28(m，4H)，7.13(d，J＝8.3Hz，2H)，6.74(d， J＝8.3Hz，2H)，6.60(s，2H)，5.67(s，1H)，4.79(br s，1H)；13C NMR(100MHz，CDCl3)δ154.1， 135.45，135.37，129.7，128.6，125.0，124.7，122.3，119.3，115.3，112.6，39.1.C23H17Br2N2O[M+H]+ 494.9702，found(ESI+)494.9707.
4- (bis (5-bromo-1H-indol-3-yl) methyl) -2-methoxyphenol (I-16), violet solid; the yield is 85 percent; melting point 233-;1H NMR(400MHz，CDCl3)δ7.99(s，2H)，7.49(s，2H)，7.23-7.26(m，4H)，6.73-6.85(m，3H)， 6.65(s，2H)，5.68(s，1H)，5.53(s，1H)，3.79(s，3H)；13C NMR(100MHz，CDCl3)δ14.9，146.5， 135.4，128.7，125.0，124.7，122.3，121.2，119.4，117.6，114.2，112.7，112.6，111.3，55.9，39.6. C24H19Br2N2O2[M+H]+524.9808，found(ESI+)524.9811.
3, 3' - ((3, 4-dimethoxyphenyl) methine) bis (5-bromo-1H-indole) (I-17.) red solid; the yield is 96 percent; melting point 124-;1H NMR(400MHz，CDCl3)δ8.07(s，2H)，7.48(s，2H)，7.20-7.26(m，4H)，6.85(s， 1H)，6.77(s，2H)，6.62(s，2H)，5.69(s，1H)，3.85(s，3H)，3.76(s，3H)；13C NMR(100MHz，CDCl3) δ148.8，147.5，135.8，135.4，128.6，124.9，124.8，122.3，120.5，119.2，112.7，112.0，111.0，55.9， 39.5.C25H21Br2N2O2[M+H]+538.9964，found(ESI+)538.9967.
3, 3' - ((3, 4, 5-trimethoxyphenyl) methine) bis (5-bromo-1H-indole) (I-18.) a pink solid; the yield is 78 percent; melting point 258-;1H NMR(400MHz，DMSO-d6)δ11.06(s，2H)，7.50(s，2H)，7.34(d，J＝8.6Hz，2H)， 7.16(dd，J＝1.5，8.6Hz，2H)，6.97(d，J＝1.9Hz，2H)，6.71(s，2H)，5.80(s，1H)，3.67(s，6H)，3.64 (s，3H)；13C NMR(100MHz，DMSO-d6)δ153.1，140.5，136.3，135.7，128.9，125.7，123.9，121.7， 118.1，114.0，111.3，106.3，60.5，56.3，39.6.C26H23Br2N2O3[M+H]+569.0070，found(ESI+) 569.0065.
3, 3' - ((4-fluorophenyl) methylidene) bis (5-bromo-1H-indole) (I-19.) as a pink solid; the yield is 48 percent; melting point 120-;1H NMR(400MHz，CDCl3)δ8.01(s，2H)，7.45(s，2H)，7.22-7.29(m，6H)，6.99(d，J＝8.6Hz，2H)， 6.63(s，2H)，5.74(s，1H)；13C NMR(100MHz，CDCl3)δ135.4，130.0，129.9，128.5，125.1，124.7， 122.2，119.0，115.4，115.1，112.8，112.6，39.2.C23H16Br2FN2[M+H]+496.9659，found(ESI+) 496.9665.
3, 3' - ((4-nitrophenyl) methine) bis (5-bromo-1H-indole) (I-20.) as a yellow solid; the yield is 88%; melting point 195-196 deg.C;1H NMR(400MHz，CDCl3)δ8.13-8.16(m，4H)，7.44(d，J＝8.65Hz，2H)，7.43(s，2H)，7.25-7.30 (m，2H)，6.74(d，J＝8.34Hz，2H)，6.65(d，J＝2.09Hz，2H)，5.85(s，1H)；13C NMR(100MHz， CDCl3)δ150.9，146.8，135.4，129.4，128.3，125.4，124.9，123.9，121.9，117.4，113.0，112.9，39.8. C23H16Br2N3O2[M+H]+523.9604，found(ESI+)523.9607.
3, 3' - ((4- (trifluoromethyl) phenyl) methine) bis (5-bromo-1H-indole) (I-21) pink solid; the yield is 49%; melting Point 129-131℃；1H NMR(400MHz，CDCl3)δ8.06(s，2H)，7.55(d，J＝8.1Hz，2H)，7.45(s，2H)， 7.39(d，J＝8.0Hz，2H)，7.23-7.28(m，4H)，6.61-6.62(m，2H)，5.81(s，1H)；13C NMR(100MHz， CDCl3)δ147.2，135.4，128.9，128.5，125.5，125.4，125.3，124.8，122.1，118.1，112.9，112.8，60.5， 39.8.C24H16Br2F3N2[M+H]+546.9627，found(ESI+)546.9631.
3, 3' - ((2-bromophenyl) methine) bis (5-bromo-1H-indole) (I-22.) a pink solid; the yield is 65%; melting point 227-;1H NMR(400MHz，CDCl3)δ8.01(s，2H)，7.64-7.67(m，1H)，7.50-7.51(m，2H)，7.25-7.31(m，4H)， 7.13-7.20(m，3H)，6.62(d，J＝1.7Hz，2H)，6.19(s，1H)；13C NMR(100MHz，CDCl3)δ135.4， 133.1，130.1，128.6，128.2，127.4，125.2，125.0，122.2，117.8，112.8，112.6，39.3.C23H16Br3N2 [M+H]+556.8858，found(ESI+)556.8854.
3, 3' - (naphthalen-1-ylmethylidene) bis (5-bromo-1H-indole) (I-23.) pink solid; the yield is 88%; melting point 294-;1H NMR(400MHz，CDCl3)δ8.06(d，J＝8.4Hz，1H)，7.96(s，2H)，7.90(d，J＝8.2Hz，1H)，7.77(d， J＝8.3Hz，1H)，7.45-7.49(m，3H)，7.40(t，J＝8.0Hz，1H)，7.32(t，J＝7.3Hz，1H)，7.24-7.29(t， 4H)，7.16(d，J＝6.9Hz，1H)，6.56(s，2H)，6.52(s，1H)；13C NMR(100MHz，CDCl3)δ135.4， 134.1，128.8，128.7，127.4，126.1，126.0，125.5，125.1，124.1，122.2，118.7，112.8，112.7，35.6. C27H19Br2N2[M+H]+528.9910，found(ESI+)528.9916.
2, 2-bis (5-bromo-1H-indol-3-yl) -1- (1H-indol-3-yl) ethan-1-one (I-24). red solid; the yield is 65%; melting point 194 ℃ and 195 ℃;1H NMR(400MHz，CDCl3)δ8.95(s，1H)，8.45-8.47(m，1H)，8.15(s，2H)，7.85(d， J＝3.1Hz，1H)，7.68(d，J＝1.4Hz，2H)，7.38-7.41(m，1H)，7.29-7.31(m，1H)，7.20-7.23(m， 3H)，7.12-7.14(m，2H)，6.81(d，J＝2.0Hz，2H)，6.11(s，1H)；13C NMR(100MHz，CDCl3)δ 175.7，135.1，132.1，128.4，126.0，125.1，123.9，122.9，122.5，121.4，114.3，113.0，111.7，43.4. C26H18Br2N3O[M+H]+545.9811，found(ESI+)545.9810.
3, 3' - (furan-2-ylmethylidene) bis (5-bromo-1H-indole) (I-25). grey solid; the yield is 93 percent; melting point 179-180 ℃;1H NMR(400MHz，CDCl3)δ8.00(s，1H)，7.56(s，2H)，7.37(s，1H)，7.20-7.37(m，5H)，6.85(s，2H)， 6.32(s，1H)，6.04(d，J＝2.6Hz，1H)，5.80(s，1H)；13C NMR(100MHz，CDCl3)δ156.1，141.6， 135.2，128.4，125.0，124.2，122.1，116.5，112.8，112.7，110.3，107.0，34.0.C21H15Br2N2O[M+H]+ 468.9546，found(ESI+)468.9553.
example 2: the activity against tobacco mosaic virus was determined by the following procedure:
1. virus purification and concentration determination:
virus purification and concentration determinations were performed in accordance with the tobamovirus SOP specifications compiled by the institute of elements institute of south-opening university. Centrifuging the virus crude extract with polyethylene glycol for 2 times, measuring concentration, and refrigerating at 4 deg.C for use.
2. Compound solution preparation:
weighing, adding DMF to dissolve to obtain 1 × 10 solution5Diluting the mother liquor with mu g/mL by using an aqueous solution containing 1 per mill of Tween 80 to the required concentration; the ningnanmycin preparation is directly diluted by adding water.
3. The protection effect of the living body is as follows:
selecting 3-5 leaf-period Saxisi tobacco with uniform growth, spraying the whole plant, repeating for 3 times, and setting 1 ‰ Tween 80 aqueous solution as control. After 24h, the leaf surfaces are scattered with carborundum (600 meshes), the virus liquid is dipped by a writing brush, the whole leaf surfaces are lightly wiped for 2 times along the branch vein direction, the lower parts of the leaf surfaces are supported by palms, the virus concentration is 10 mu g/mL, and the inoculated leaf surfaces are washed by running water. And recording the number of the disease spots after 3d, and calculating the prevention effect.
4. Therapeutic action in vivo:
selecting 3-5 leaf-stage Saxismoke with uniform growth vigor, inoculating virus with whole leaf of writing brush at a virus concentration of 10 μ g/mL, and washing with running water after inoculation. After the leaves are harvested, the whole plant is sprayed with the pesticide, the treatment is repeated for 3 times, and a 1 per mill tween 80 aqueous solution is set for comparison. And recording the number of the disease spots after 3d, and calculating the prevention effect.
5. The living body passivation effect is as follows:
selecting 3-5 leaf-period Saxismoke with uniform growth, mixing the preparation with virus juice of the same volume, inactivating for 30min, performing friction inoculation with virus concentration of 10 μ g/mL, washing with running water after inoculation, repeating for 3 times, and setting 1 ‰ Tween 80 water solution as control. The number of lesions after 3d was counted and the result was calculated.
Inhibition (%) < percent [ (control number of scorched spots-number of treated scorched spots)/control number of scorched spots ]. times.100%
The in-vivo inactivation activity test of all compounds against tobacco mosaic virus is firstly carried out under the condition of a treatment dose of 500 mu g/mL, and the in-vivo treatment and activity protection activity test under the condition of a treatment dose of 500 mu g/mL is further carried out on the compounds with the relative inhibition rate of more than 40%. The positive control is commercial anti-plant virus agent ribavirin.
TABLE 1 results of activity test of alkaloid arnodine and its derivatives I-1-I-25 against Tobacco Mosaic Virus (TMV)
As can be seen from the data in Table 1, the alkaloid arnodine and the derivatives I-1 to I-25 thereof all show good anti-TMV activity, the activity of 4 compounds is equivalent to that of ribavirin, the activity of 9 compounds is obviously superior to that of ribavirin, and the alkaloid arnodine and the derivatives I-1 to I-25 thereof have great development value.
Example 3: antibacterial activity test, the determination procedure is as follows:
in vitro bactericidal assay, cell growth rate assay (plate method):
dissolving a certain amount of medicament in a proper amount of acetone, then diluting the solution to a required concentration by using an emulsifier aqueous solution containing 200 mug/mL, sucking 1mL of liquid medicine respectively, injecting the liquid medicine into a culture dish, adding 9mL of culture medium respectively, shaking the liquid medicine uniformly to prepare a medicine-containing plate with 50 mug/mL, and taking the plate added with 1mL of sterilized water as a blank control. Cutting the plate with a punch with diameter of 4mm along the outer edge of the hypha, and transferring to a medicated plate. Each treatment was repeated three times. The culture dish is placed in a constant temperature incubator at 24 +/-1 ℃ for culture. And after 48 hours, investigating the expansion diameter of each treated bacterium disc, calculating an average value, and comparing with a blank control to calculate the relative bacteriostasis rate.
Table 2 in vitro bactericidal activity test results for the alkaloid arnodine and its derivatives I-1 to I-25:
the alkaloid arnodine and the derivatives thereof show broad-spectrum inhibitory activity on 14 tested bacteria under the condition that the test concentration is 50 mu g/mL. The various compounds showed superior activity to the control chlorothalonil against various strains. The compound I-7 shows excellent inhibitory activity against 14 test bacteria, EC50The value is 12.6-38.5 mu g/mL, and the method has great development value.
The starting materials and reagents involved in the above examples were prepared by commercially available or literature-referenced methods, and the chemical reaction procedures were within the skill of the art.
Claims (3)
1. An application of alkaloid arnodine and derivatives thereof in preventing and treating plant virus and bacterial diseases is disclosed, wherein the alkaloid arnodine and the derivatives thereof are one of the following structural formulas I-1-I-25:
2. the use of an alkaloid, arnodine and its derivatives, as claimed in claim 1 for the control of phytopathogenic viruses, wherein said viruses are tobacco mosaic viruses.
3. The use of an alkaloid arnodine and derivatives thereof for controlling plant viral pathogens as claimed in claim 1, wherein the pathogens are 14 species of phytophthora parasitica, cucumber wilt, peanut brown spot, apple ring rot, wheat sheath blight, corn millet spot, watermelon anthracnose, rice bakanae, tomato early blight, wheat gibberella, rice blast, phytophthora capsici, rape sclerotium, cucumber gray mold, rice sheath blight.
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| CN105454237A (en) * | 2015-12-25 | 2016-04-06 | 江苏省中国科学院植物研究所 | Application of diindolylmethane compound in pesticide |
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