CN112136824A - Application of quassin compounds in preventing and treating plant fungal diseases - Google Patents
Application of quassin compounds in preventing and treating plant fungal 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
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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Abstract
The invention belongs to the technical field of pesticides, and particularly relates to an application of quassinoid compounds in preventing and treating plant fungal diseases, wherein the quassinoid compounds are separated from Eurycoma longifolia Willd of Simaroubaceae, and researches show that the quassinoid compounds have inhibitory activity on various plant fungi and can be applied to preventing and treating plant fungal diseases; meanwhile, the compounds have systemic property, can be transported and guided in plants, have better antibacterial effect than a bactericide applied to the surfaces of the plants, can be used for preparing systemic fungicides, are more convenient to use, have no interference of external environment on control effect, and have good application prospect.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to an application of quassinoid compounds in preventing and treating plant fungal diseases.
Background
Plant invasive diseases can be divided into bacterial diseases, fungal diseases, viral diseases, nematode diseases and the like, wherein the fungal diseases are the most common and common disease types in crop diseases, and almost 80 percent of the plant invasive diseases are caused by fungi. The diseases are various in types, the expression symptoms are varied, the yield of crops is reduced, the quality of agricultural products is reduced, and the agricultural products can be even poisoned by some fungal diseases, so that the health of people and livestock is endangered. Therefore, controlling plant fungal diseases has long been a challenge for scientists to struggle with. Although breeding resistant varieties is the most economical and environmentally friendly method for controlling the diseases, the use of chemical agents in the case of lack of resistant varieties or incomplete resistance is still the main means for controlling fungal diseases of crops. With the widespread use of fungicides, many problems have arisen, the most important of which are resistance and residue problems. At present, the chemical control effect is reduced or failed due to the increase of the resistance of crops to pathogenic bacteria in many areas, and therefore, farmers generally adopt a mode of blindly increasing the dosage of bactericides or mixing a plurality of medicaments to improve the control effect, so that the severity of the residue problem is further increased, which is a main root cause of pesticide residue and environmental pollution in our country. Therefore, with the increasingly prominent side effects of chemical pesticides and the gradual increase of the requirements of people on environment-friendly and green foods, the research and development of biological pesticides which accord with the concepts of environment protection, health and sustainable development becomes urgent.
Sima (Sima)roubaceae) plants are deciduous or evergreen shrubs or trees, and are mainly distributed in tropical and subtropical regions such as africa, america, and southeast asia. The Simaroubaceae plant comprises more than 20 species of 120 species at present, and 5 species of 11 species of native plants in our country, which are mainly distributed in the south provinces of the Yangtze river, and comprise Picrasma (Picrasma), Ailanthus (Ailanthus), Brucea (Brucea), Elaeagnus (Harrisonia) and Hippocampus (Suriana). The bark of plants of the Simaroubaceae family is often bitter in taste and is therefore named. Quassinoids (Quassinoids) are bitter compounds, are mostly highly oxidized nortriterpenoids, are characteristic chemical components of plants in Simaroubaceae, and are also main active components of the plants. At present, more than 400 quassinoids are separated and identified from different plants of the Simaroubaceae family, and can be classified as C according to the number of carbon atoms contained in the skeleton25、 C22、C20、C19And C18Five subtypes. The compounds have various skeleton types, have pharmacological actions of resisting malaria, tumors, inflammation and viruses in medicine, have various biological activities of antifeedant, poison and the like to insects in agriculture, and are one of the research hotspots of natural product chemists and pharmacologists all the time. However, no related research on the plant disease fungus resistance of the quassinoid compounds exists at present. Therefore, picrasma quassioides of plant origin is a new important research direction in the field of resistance to plant fungi.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the application of the quassinoid compound in preventing and treating plant fungal diseases.
In order to achieve the purpose, the invention adopts the technical scheme that:
the first purpose of the invention is to provide the application of quassinoid compounds in preventing and treating plant fungal diseases.
The second purpose of the invention is to provide the application of the quassinoid compound in preparing the medicament for preventing and treating plant fungal diseases.
According to research, the quassinoid compounds separated from Eurycoma longifolia (Eurycoma longifolia) of the Simaroubaceae have excellent bacteriostatic activity on various plant fungi, and the quassinoid compounds have systemic property, can be transported in plants, have better bacteriostatic action compared with a medicament applied to the surface of the plants, and are more convenient to use.
Preferably, in the above two applications of the present invention, the quassinoid compound is selected from C shown in the following structural formula19Picrasma quassioides bitter principle compounds and C20At least one of the quassin compounds:
more preferably, C is19The quassinoid compound is selected from at least one of the following structural formulas:
said C is20The quassinoid compound is selected from at least one of the following structural formulas:
specifically, in the above structural formulas, compound 2 (eurycolide B) corresponding to structural formula 2, compound 3 (eurycolone) corresponding to structural formula 3, compound 5 (eurycolone B) corresponding to structural formula 5, compound 7(13, 21-dihydroeuronone) corresponding to structural formula 7, compound 8 (eurycolone) corresponding to structural formula 8, and compound 9(longifolactone E) corresponding to structural formula 9.
Preferably, in both of the above applications of the present invention, the plant fungal diseases include, but are not limited to, banana vascular wilt, papaya anthracnose, guava leaf blight, potato dry rot, apple rot and tomato early blight.
The third purpose of the invention is to provide a fungicide which can be transported in plants, and the active ingredient of the fungicide comprises quassinoid compounds.
Preferably, in the fungicide of the present invention, the quassinoid compound is selected from C represented by the following structural formula19Picrasma quassioides bitter principle compounds and C20At least one of the quassin compounds:
more preferably, C is19The quassinoid compound is selected from at least one of the following structural formulas:
said C is20The quassinoid compound is selected from at least one of the following structural formulas:
specifically, in the above structural formulas, compound 2 (eurycolide B) corresponding to structural formula 2, compound 3 (eurycolone) corresponding to structural formula 3, compound 5 (eurycolone B) corresponding to structural formula 5, compound 7(13, 21-dihydroeuronone) corresponding to structural formula 7, compound 8 (eurycolone) corresponding to structural formula 8, and compound 9(longifolactone E) corresponding to structural formula 9.
Preferably, in the fungicide of the present invention, the quassinoid compound is contained in the fungicide in an amount of 1% to 70% by weight.
Preferably, in the fungicide of the present invention, the formulation of the fungicide includes, but is not limited to, aqueous emulsion, microemulsion, dry suspension.
Researches show that the quassin compounds prepared into an aqueous emulsion, a microemulsion or a dry suspending agent have better field control effects on banana vascular wilt, papaya anthracnose and guava leaf blight. Among them, the control effect of the compound 8(eurycomanone) is the most significant.
In particular, the invention also provides plant fungicides in several specific formulations, as follows:
(1) a fungicide aqueous emulsion capable of being transported in plants is specifically composed of the following components in percentage by weight:
1 to 20 percent of picrasma quassioides picrorhiza compounds, 1 to 5 percent of solvent, 1 to 5 percent of emulsifier, 1 to 5 percent of co-emulsifier, 1 to 2 percent of antifreeze, 0.4 to 0.6 percent of density regulator, 0.05 to 0.15 percent of pH value regulator, 0.05 to 0.15 percent of defoamer and 62.1 to 94.5 percent of water.
Preferably, the antifungal aqueous emulsion consists of the following components in percentage by weight:
1% of quassinoid compounds, 2% of solvent, 2% of emulsifier, 2% of co-emulsifier, 1% of antifreeze, 0.5% of density regulator, 0.1% of pH value regulator, 0.1% of defoamer and 91.3% of water.
Preferably, in the above fungicidal aqueous emulsions, the solvent includes, but is not limited to, methanol; the emulsifier includes but is not limited to Nongru No. 600, Nongru No. 500, Ningru No. 130, Tween 80; the coemulsifiers include, but are not limited to, butanol, isobutanol, 1-dodecanol, 1-tetradecanol; such anti-freeze agents include, but are not limited to, glycerol; the density modifiers include, but are not limited to, sodium chloride, calcium chloride; the pH regulator includes but is not limited to phosphoric acid, the defoamer includes but is not limited to octadecyl trimethyl ammonium chloride, and the water is deionized water.
(2) A fungicide microemulsion capable of being transported in plants is specifically composed of the following components in percentage by weight:
30-50% of quassinoid compounds, 8-10% of solvent, 8-10% of emulsifier, 2-3% of stabilizer, 5-10% of antifreezing agent and 17-47% of water.
Preferably, the fungicidal microemulsion consists of the following components in percentage by weight:
40% of quassinoid compounds, 10% of solvent, 10% of emulsifier, 3% of stabilizer, 8% of antifreezing agent and 29% of water.
Preferably, in the above fungicidal microemulsions, the solvent includes, but is not limited to, methanol; the emulsifier includes but is not limited to Nongru No. 700, Nongru No. 300, sodium diisooctyl succinate sulfonate; the stabilizer includes, but is not limited to, o-tolyl glycidyl ether, n-butyl glycidyl ether; the antifreeze includes but is not limited to propylene glycol, ethylene glycol and glycerol, and the water is deionized water.
(3) A fungicidal dry suspending agent capable of being transported in plants is specifically composed of the following components in percentage by weight:
60-80% of quassin compounds, 10-35% of dispersing agent and 5-10% of emulsifying agent.
Preferably, the fungicidal dry suspension consists of the following components in percentage by weight:
70% of quassin compounds, 25% of dispersing agent and 5% of emulsifying agent.
Preferably, in the above fungicidal dry suspension, the dispersant is a cottonseed cake protein hydrolysate, the solids content of the cottonseed cake protein hydrolysate being 40%; the emulsifier includes, but is not limited to, tween 80.
Compared with the prior art, the invention has the beneficial effects that:
the invention discloses a picrasma quassioides compound separated from Eurycoma longifolia Roxb of Simaroubaceae, which is found through research to have inhibitory activity on various plant fungi, can be transported in plants, has better inhibitory action than a bactericide applied to the surfaces of the plants, can be applied to preventing and treating plant fungal diseases, and is prepared into a medicament for preventing and treating plant fungal diseases (particularly into a systemic plant antifungal bactericide), so that the picrasma quassioides compound is more convenient to use (for example, the picrasma quassioides compound is added into plant irrigation water, the application is finished while the plants are watered), the prevention effect is not interfered by the external environment, and the picrasma quassioides compound has good application prospect.
Detailed Description
The following further describes the embodiments of the present invention. It should be noted that the description of the embodiments is provided to help understanding of the present invention, but the present invention is not limited thereto. In addition, the technical features involved in the embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The test methods used in the following examples are all conventional methods unless otherwise specified; the materials, reagents and the like used are all commercially available reagents and materials unless otherwise specified.
Example 1: extraction separation and structural identification of quassinoid compounds in Eurycoma longifolia Robusta of Simaroubaceae
10kg of Eurycoma longifolia Roxb root is crushed into coarse powder, the coarse powder is extracted by cold soaking with 95% ethanol, the extracting solutions are combined and concentrated under reduced pressure to obtain 270g of total extract. Suspending the total extract with water, sequentially extracting with petroleum ether, ethyl acetate and n-butanol, and recovering solvent under reduced pressure to obtain petroleum ether fraction (40g), ethyl acetate fraction (99g), n-butanol fraction (85g) and water fraction (26 g).
The petroleum ether fractions were subjected to silica gel column chromatography, gradient elution with chloroform-methanol system (100:0 → 0:100, v/v), and TLC analysis to give 7 major fractions (Fr.a-Fr.g).
E was chromatographed on ODS column with methanol-water gradient (20:80 → 100:0, v/v) and combined by TLC to give Fr. e1-Fr.e 5. Wherein, compound 1(120.7mg), compound 2(200.0mg), compound 3(103.5mg), compound 4(14.0mg), compound 5(415.8mg), compound 6(1.5g), compound 7(105.4mg), compound 8(85.6mg), and compound 9(52.0mg) were obtained by separation and purification of fr.e. 3 and fr.e. 4 by repeated ODS column chromatography, Sephadex LH-20, and high performance liquid chromatography, respectively.
The structure of each compound is identified by a wave spectrum method, and each physical and chemical data and spectrum data are as follows:
compound 1
Colorless needle crystals (methanol), mp 195-196 ℃,
(c 0.65, methanol); UV (acetonitrile) lambdamax(log)： 235(3.99)nm；IR(KBr)vmax：3442,1774,1660,1458,1333,1261,1178,1114,1053,964,932,875, 750,600cm-1；HR-ESI-MS：m/z 373.1621[M+Na]+(calcd for C19H26O6Na,373.1622)；1H NMR (300MHz,C5D5N)5.91(s,1H),4.16(m,1H),5.76(q,J＝5.0Hz,1H),4.48(dd,J＝5.0,1.3Hz, 1H),3.54(d,J＝8.6Hz,1H),3.36(brs,1H),3.30(q,J＝7.0Hz,1H),2.53(dt,J＝12.4,4.5Hz, 1H),2.45(m,1H),2.12(dt,J＝12.4,4.5Hz,1H),1.91(s,3H),1.67(s,3H),1.22(q,J＝12.4Hz, 1H),1.04(d,J＝6.9Hz,3H),0.93(d,J＝6.4Hz,3H)；13C NMR(75MHz,C5D5N)199.9,177.7, 171.4,120.9,85.6,85.2,70.8,69.7,53.4,48.8,48.2,46.9,41.1,32.6,32.1,23.1,18.6,17.8,17.2。
Compound 2
Colorless needle crystals (methanol), mp 215-,
(c 0.58, methanol); UV (acetonitrile) lambdamax(log)： 282(4.03)nm；IR(KBr)vmax：3481,1766,1711,1655,1581,1458,1384,1327,1262,1174,1054, 958,932,882,715,621cm-1；HR-ESI-MS：m/z 371.1460[M+Na]+(calcd for C19H24O6Na, 371.1465)；1H NMR(400MHz,C5D5N)6.24(brs,1H),6.11(s,1H),6.02(m,1H),4.73(brs,1H), 4.54(m,1H),3.97(d,J＝7.3Hz,1H),3.44(d,J＝1.2Hz,1H),3.35(q,J＝6.9Hz,1H),2.63(d,J ＝3.2Hz,1H),1.92(s,3H),1.82(s,3H),1.80(s,3H),1.08(d,J＝6.9Hz,3H)；13C NMR(100 MHz,C5D5N)200.0,177.8,163.6,138.1,131.5,121.7,85.4,83.6,72.1,70.1,53.9,48.3,47.3, 46.1,32.8,24.1,20.3,17.3,16.8。
Compound 3
Colorless needle crystals (methanol), mp 251-,
(c 0.29, methanol); UV (acetonitrile) lambdamax(log )：240(3.97)nm；IR(KBr)vmax：3459,2952,1734,1667,1436,1381,1261,1122,961,818,631 cm-1；HR-ESI-MS：m/z 371.1461[M+Na]+(calcd for C19H24O6Na,371.1465)；1H NMR(400MHz, CDCl3)6.09(s,1H),4.77(m,1H),4.35(d,J＝4.7Hz,1H),4.03(s,1H),2.92(brs,1H),2.91(m, 1H),2.87(m,1H),2.78(overlapped,2H),1.93(s,3H),1.86(d,J＝3.6Hz,1H),1.54(s,3H),1.23 (s,3H),1.14(d,J＝7.0Hz,3H)；13C NMR(100MHz,CDCl3)205.6,197.5,176.3,162.3,124.5, 83.2,81.3,69.9,53.0,51.2,49.4,49.1,47.0,36.3,32.4,23.7,22.0,16.7,12.2。
Compound 4
Colorless needle crystals (methanol), mp 270-,
(c 0.25, methanol); UV (acetonitrile) lambdamax(log )：240(4.08)nm；IR(KBr)vmax：3527,3434,3392,1737,1668,1389,1226,1136,1120,1049, 990cm-1；HR-ESI-MS m/z 419.1309[M+Na]+(calcd for C19H24O9Na,419.1313)；1H NMR(400 MHz,C5D5N)5.10(s,1H),5.09(m,1H),5.54(br s,1H),4.15(t, J ═ 4.4Hz,1H),4.74(d, J ═ 9.1Hz,1H) and 3.93(d, J ═ 9.1Hz,1H),2.51(s,3H),1.75(d, J ═ 7.2Hz,3H) and 1.57(s, 3H);13C NMR (100MHz,C5D5N)174.8,173.0,170.5,119.4,111.3,92.5,82.5,81.8,75.7,71.4,69.0,63.6,47.5, 47.3,46.4,43.8,18.7,16.5,13.4。
compound 5
Colorless columnar crystals (methanol), mp 245-,
(c 0.89, methanol); UV (acetonitrile) lambdamax(log )：212(3.65)nm；IR(KBr)vmax：3427,1736,1632,1440,1386,1315,1193,1120,1076,1042, 987,889,847,817,733cm-1；HR-ESI-MS m/z 417.1154[M+Na]+(calcd for C19H22O9Na, 417.1156)；1H NMR(300MHz,C5D5N)6.09(d,J＝1.4Hz,1H),5.60(d,J＝1.4Hz,1H),6.00(s, 1H),5.71(s,1H),5.19(s,1H),5.14(d,J＝4.8Hz,1H),4.83(s,1H),3.93(s,1H)2.58(s,3H),1.60 (s,3H)；13C NMR(75MHz,C5D5N)174.0,173.0,170.5,149.6,119.7,119.4,110.6,92.5,83.1, 83.1,78.3,72.3,69.0,63.4,48.3,47.8,46.5,18.7,16.6)
Compound 6
Colorless columnar crystals (methanol), mp 267-268 ℃,
(c 0.51, methanol); UV (acetonitrile) lambdamax(log )：241(4.05)nm；IR(KBr)vmax：3425,2945,1726,1660,1435,1381,1344,1262,1122,1064, 998,964,902,818,773,698,565,525cm-1；HR-ESI-MS m/z 419.1674[M+Na]+(calcd for C20H28O8Na,419.1676)；1H NMR(400MHz,CDCl3)6.09(s,1H),5.36(s,1H),4.90(t,J＝2.8 Hz,1H),4.63(t,J＝3.0Hz,1H),4.03(s,1H),3.90(t,J＝2.6Hz,1H),2.88(d,J＝13.7Hz,1H), 2.43(qd,J＝7.3,3.2Hz,1H),2.29(dt,J＝14.4,2.9Hz,1H),2.11(overlapped,1H),2.10(m,1H), 1.97(s,3H),1.52(s,3H),1.23(d,J＝7.3Hz,3H),1.18(s,3H)；13C NMR(100MHz,CDCl3) 198.2,175.9,164.5,124.4,82.7,81.5,77.0,75.9,73.7,71.2,48.2,45.0,43.6,43.1,35.9,26.1,22.8, 17.4,12.5,12.4。
Compound 7
Colorless needle crystals (methanol), mp 289-,
(c 0.61, methanol); UV (acetonitrile) lambdamax(log )：241(4.07)nm；IR(KBr)vmax：3466,2952,2906,2717,1733,1653,1496,1389,1313,1227, 1126,1056,1014,966,817,766cm-1；HR-ESI-MS m/z 433.1463[M+Na]+(calcd for C20H26O9Na, 433.1469)；1H NMR(300MHz,C5D5N)6.13(s,1H),5.64(s,1H),5.22(d,J＝2.9Hz,1H),4.66 (d,J＝9.1Hz,1H),4.40(s,1H),4.15(brs,1H),4.06(d,J＝9.0Hz,1H),3.53(s,1H),3.18(d,J＝ 12.6Hz,1H),2.86(m,1H),2.28(dt,J＝14.7,3.0Hz,1H),2.04(td,J＝15.0,12.8,2.4Hz,1H), 1.87(d,J＝6.6Hz,3H),1.77(s,3H),1.63(s,3H)；13C NMR(75MHz,C5D5N)197.9,175.2, 163.1,126.4,110.7,84.9,80.0,76.9,75.4,72.3,67.7,53.1,47.3,46.0,42.6,42.5,26.1,22.8,14.5, 11.0。
Compound 8
Colorless needle crystals (methanol), mp 285-,
(c 0.65, methanol); UV (acetonitrile) lambdamax(log )：241(3.46)nm；IR(KBr)vmax：3410,1737,1673,1622,1504,1435,1385,1357,1313,1261, 1230,1156,1121,943,915,866,826,765,697cm-1；HR-ESI-MS m/z 431.1314[M+Na]+(calcd for C20H24O9Na,431.1313)；1H NMR(300MHz,C5D5N)6.16(brs,1H),6.12(d,J＝1.8Hz,1H), 5.67(s,1H),5.65(d,J＝1.7Hz,1H),5.26(t,J＝2.9Hz,1H),4.81(s,1H),4.55(d,J＝8.6Hz,1H), 4.52(s,1H),4.02(d,J＝8.6Hz,1H),3.82(s,1H),3.26(d,J＝12.5Hz,1H),2.33(dt,J＝14.9,2.8 Hz,1H),2.02(td,J＝15.1,12.9,2.5Hz,1H),1.78(s,3H),1.62(s,3H)；13C NMR(75MHz,C5D5N) 197.9,174.3,162.9,148.4,126.4,119.7,109.9,84.9,81.3,79.8,76.2,72.1,68.0,52.9,48.1,46.3, 42.5,26.0,22.8,10.8。
Compound 9
Colorless needle crystals (methanol), mp 260-,
(c 0.19, methanol); UV (acetonitrile) lambdamax(log )：200(3.60)nm；IR(KBr)vmax：3508,3304,1727,1629,1390,1308,1246,1213,1116,1041,993, 890,850,816,735,709,661cm-1；HR-ESI-MS m/z 449.1420[M+Na]+(calcd for C20H26O10Na, 449.1418)；1H NMR(400MHz,C5D5N)5.81(s,1H),5.70(s,1H),5.11(br s,1H),4.65(br s,1H), 4.08(overlapped,1H),4.05(s,1H),4.88(d, J ═ 8.9Hz,1H),4.11(d, J ═ 8.9Hz,1H),1.76(s,3H) and 1.64(s, 3H);13C NMR(100MHz,C5D5N)174.3,135.4,127.4,110.2,84.0,82.2,76.6,75.9, 73.1,72.0,67.5,59.9,54.1,49.0,47.0,42.7,42.0,25.8,21.7,11.4。
the compounds 1-9 have the following structural formulas, respectively, as determined by structural identification:
wherein, the structural formula 1 corresponds to a compound 1, which is eurycolide A; structural formula 2 corresponds to compound 2, which is eurycolide B; compound 3 corresponding to formula 3, is eurycomaldone; the compound 4 corresponding to the structural formula 4 is 13,21-dihydroeurylactone B; compound 5 corresponding to formula 5 is eurylactone B; compound 6 corresponding to structural formula 6 is 14,15 β -dihydroklainanenone; a compound 7 corresponding to formula 7, which is 13, 21-dihydroeurycolone; compound 8 corresponding to formula 8 is eurycomanone; compound 9, corresponding to formula 9, is longifolactone E.
Example 2: inhibition of plant pathogenic fungi by quassin compounds
(1) Test drug
Picrasma quassioides picrorhizin compound (compound 1-9), prochloraz (positive control compound, commercial pesticide).
(2) Test fungal species
The tested fungus strains are 6, and are fusarium causing banana wilt, colletotrichum gloeosporioides of papaya anthracnose, new Fusarium solani causing guava leaf blight, fusarium solani causing potato dry rot, pericarp and botrytis cinerea causing apple rot, respectively.
(3) Determination of anti-plant-fungal Activity
Preparation of test bacterium plates: under aseptic condition, respectively inoculating pure test bacteria to a sterile PDA culture medium plate by a dense wave line drawing method, culturing at 27 deg.C for about one week, and allowing the plate to grow bacterial lawn.
Preparation of the culture medium and sterilization thereof: the culture medium is PDA solid culture medium, and the formula is as follows: 200g of potato, 20g of glucose, 20g of agar and 1000mL of tap water. The preparation process comprises the following steps: cutting peeled potato into 5mm square pieces, adding tap water, boiling for 20min, filtering with 8 layers of gauze, adding corresponding amount of glucose and agar powder into the filtrate, heating and stirring to dissolve, adding tap water to desired volume, packaging into 250mL triangular bottles, sealing (each bottle contains 100mL culture medium), and sterilizing with autoclave at 115 deg.C for 30 min.
Preparing a liquid medicine: weighing 1.00mg of prochloraz and quassinoid compounds (compounds 1-9) respectively in a 1.5mL sterile centrifuge tube, and adding 1mL of acetone respectively to dissolve.
Preparation of a culture medium with medicine: heating and melting the culture medium in a sterilized triangular flask, cooling to about 50 ℃, respectively adding the prepared liquid medicine on a super-clean workbench through aseptic operation, slightly shaking the triangular flask to uniformly distribute the liquid medicine in the culture medium, preparing the quassia picrosinoids compound into a culture medium with medicine with a final concentration of 50ug/mL, immediately pouring the culture medium with medicine into 5 sterile culture dishes (20 mL of culture medium in each culture dish) while the culture medium is hot to prepare flat plates with uniform thickness, and marking, wherein prochloraz is a positive control; in the same procedure, plates of negative control acetone (ImL added directly to 100mL sterile medium) were prepared and labeled.
And (3) testing the bacteriostatic rate: under the aseptic condition, punching a certain amount of fungus cakes on a test fungus flat plate by using an aseptic puncher, taking the fungus cakes by using an inoculating loop holder, placing the fungus cakes on a prepared culture medium with medicine, enabling the hypha to face downwards, marking 1 fungus cake per dish (three times), placing the fungus cakes in a thermostat at 27 ℃ for culturing for 72 hours, taking out a culture, measuring the diameter of a bacterial colony by using a caliper (measuring the cross quantity twice, measuring all three repeated flat plates, taking the average number of the three repeated flat plates), calculating the bacteriostasis rate according to the formula (1), and obtaining the calculation result of the plant fungal resistance activity of each quassinoid compound under the concentration of 50ug/mL in the table 1.
Inhibition rate (negative control growth diameter-treated growth diameter)/(negative control growth diameter-5) × 100% … (1).
As can be seen from Table 1, the 9 quassinoids of the invention have good control effects on fusarium, colletotrichum gloeosporioides, new-leaved clostridium, fusarium solani, chaetomium nigricans and botrytis cinerea, wherein the bacteriostatic rates of the compound 8(eurycomanone) and the compound 3 (eurycomalone) are all higher than 80% and the activity is better.
TABLE 1 inhibition ratio of quassinoids and prochloraz to plant fungi
Example 3: the compound 8(eurycomanone) can be absorbed into banana root from the growing environment of banana through the root and is transported upwards to inhibit banana wilt
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. Previously grown banana seedlings (6 leaf stage, not previously treated with eurycomanone) were placed in 0.5mM CaCl2Pre-culturing in water solution for 2 hr, transferring into the prepared eurycomanone culture solution, taking banana stem and leaf 0.5 g after 24 hr, mashing, dissolving in 2mL methanol, detecting the extract containing eurycomanone by high performance liquid chromatograph, and calculating to obtain the content of eurycomanone in banana stem and leaf (fresh leaf) of 67 μ g/g and 53 μ g/g. The leaf absorbed with eurycomanone is inoculated with bacteria (banana vascular wilt disease germ, No. 4 microspecies) according to the method of the embodiment 2 to carry out bacteriostatic activity experiments, and the experiments are repeated for 3 times.
The experimental result shows that the bacteriostasis rate of the banana vascular wilt germs is 87.56 percent after 7 days of treatment of the banana leaves absorbed with eurycomanone.
Example 4: the compound 8(eurycomanone) can be absorbed into the root of the pawpaw from the growing environment of the pawpaw through the root and is upwards transported to the leaf, so that the anthracnose of the pawpaw is inhibited
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. Previously grown papaya seedlings (6 leaf stage, not previously treated with eurycomanone) were placed in 0.5mM CaCl2Pre-culturing in the aqueous solution for 2 hours, transferring the aqueous solution into the prepared eurycomanone culture solution, taking 0.5 g of pawpaw leaves after 24 hours, smashing the pawpaw leaves, dissolving the pawpaw leaves in 2mL of methanol, detecting that the extract contains the eurycomanone by using a high performance liquid chromatograph, and calculating that the content of the eurycomanone in the apical leaves (fresh leaves) of the pawpaw is 47 mu g/g. The leaf absorbed with eurycomanone was inoculated with bacteria (papaya colletotrichum) according to the method of example 2, and the experiment was repeated 3 times.
The experimental result shows that the bacteriostasis rate of the papaya colletotrichum to the papaya colletotrichum is 91.71 percent 7 days after the papaya leaves absorbed with eurycomanone are treated.
Example 5: the compound 8(eurycomanone) can be absorbed into the root of guava from the growth environment of guava through the root and is transported upwards to the leaves so as to inhibit the leaf blight of guava
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. The pre-grown guava seedlings (6 leaf stage, not previously treated with euryconone) were placed in 0.5mM CaCl2Pre-culturing in water solution for 2 hr, transferring into the prepared culture solution, collecting guava leaf 0.5 g after 24 hr, mashing, dissolving in 2mL methanol, detecting with HPLC (high performance liquid chromatograph) that the extractive solution contains eurycomanone, and calculating to obtain the content of eurycomanone in guava leaf (fresh leaf) of 61 μ g/g. The leaf absorbed with eurycomanone was inoculated with the bacterium (Fusarium novellum) as described in example 2 and repeated for 3 times.
The experimental result shows that the bacteriostasis rate of the guava leaves absorbed with eurycomanone is 82.38% after 7 days of treatment.
Example 6: the compound 8(eurycomanone) can be absorbed into roots from the growing environment of round eggplant through roots and is upwards transported to leaves so as to inhibit the fusarium solani
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. Previously grown round eggplant seedlings (6 leaf stage, which had not been treated with euryconone before) were placed in 0.5mM CaCl2Pre-culturing in water solution for 2 hr, transferring into the prepared culture solution, taking 0.5 g of solanum torvum leaves after 24 hr, mashing, dissolving in 2mL of methanol, detecting that the extract contains the eurycomanone by using a high performance liquid chromatograph, and calculating that the content of the eurycomanone in the solanum torvum stems and the top leaves (fresh leaves) is 44 mug/g. The leaves absorbed with eurycomanone were inoculated with Fusarium solani (F. toruloides) as described in example 2 and tested for their bacteriostatic activity, and the procedure was repeated 3 times.
The experimental result shows that the bacteriostasis rate of the round eggplant leaves absorbed with eurycomanone is 79.62 percent after 7 days of treatment.
Example 7: the compound 8(eurycomanone) can be absorbed into the root of the apple from the growing environment of the apple through the root and is conducted upwards so as to inhibit the apple pityrosporum ovale
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. Previously grown apple seedlings (6 leaf stage, not previously treated with eurycomanone) were placed in 0.5mM CaCl2Pre-culturing in water solution for 2 hr, transferring into the prepared eurycomanone culture solution, taking 0.5 g of apple leaves after 24 hr, mashing, dissolving in 2mL of methanol, detecting the extract containing eurycomanone by high performance liquid chromatograph, and calculating to obtain 51 μ g/g of eurycomanone in the top leaves (fresh leaves) of apple. The leaf absorbed with eurycomanone is inoculated with bacteria (Humicola apple Chaetomium) according to the method of example 2 to perform an antibacterial activity experiment, and the experiment is repeated for 3 times.
The experimental result shows that the bacteriostasis rate of the apple putrefaction fungus is 79.88% 7 days after the treatment of the apple leaves absorbed with eurycomanone.
Example 8: the compound 8(eurycomanone) can be absorbed into the grape root from the growing environment of the grape through the root and is conducted upwards to inhibit botrytis cinerea
Dissolving eurycomanone in methanol to obtain 10000 ug/mL mother liquor, and adding 0.5mM CaCl2The mother liquor was diluted to 100. mu.g/mL of culture broth with the aqueous solution. Previously grown grape seedlings (6 leaf stage, not previously treated with eurycomanone) were placed in 0.5mM CaCl2Pre-culturing in water solution for 2 hr, transferring into the prepared culture solution, taking 0.5 g of grape stem and leaf after 24 hr, mashing, dissolving in 2mL of methanol, detecting the extract containing eurycomanone by high performance liquid chromatograph, and calculating to obtain the content of eurycomanone in grape top leaf (fresh leaf) of 71 μ g/g. The leaf absorbed with eurycomanone is inoculated with bacterium (botryococcus griseus) according to the method of example 2 to perform bacteriostatic activity experiments, and the experiment is repeated for 3 times.
The experimental result shows that 7 days after the treatment of the grape leaves absorbed with eurycomanone, the bacteriostasis rate of botrytis cinerea is 90.21%.
Example 9: preparation of 1% compound 8(eurycomanone) aqueous emulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. Preparing the eurycomanone into an aqueous emulsion, wherein the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 1 percent;
(2) solvent (methanol): 2 percent;
(3) emulsifier (farm milk No. 500): 2 percent;
(4) co-emulsifier (isobutanol): 2 percent;
(5) antifreeze (glycerin): 1 percent;
(6) density modifier (sodium chloride): 0.5 percent;
(7) pH adjuster (phosphoric acid): 0.1 percent;
(8) antifoam (octadecyl trimethyl ammonium chloride): 0.1 percent;
(9) water (deionized water): 91.3 percent.
The preparation method comprises the following steps: mixing the effective components, the solvent, the emulsifier and the co-emulsifier in the components, dissolving the mixture into a uniform oil phase, mixing the rest components into a uniform water phase, and adding the water phase into the oil phase under high-speed stirring to obtain the 1% eurycomanone aqueous emulsion with good dispersion.
2. The 1% eurycomanone aqueous emulsion prepared in the method is used for carrying out field tests on banana vascular wilt, papaya anthracnose and guava leaf blight, 6 treatments are set in total, each treatment is repeated for 3 times, and the area of a cell is 24m2(4m by 6m), 18 cells in total, random block arrangement, and protective rows arranged around. The test is carried out in a test base of a research institute of fruit trees of agricultural academy of sciences of Guangdong province, the conditions of soil, fertility and moisture of the test field are consistent, and the field management is basically consistent with the field production. The 1 st application is started at the initial stage of banana wilt, papaya anthracnose and guava leaf blight, the 2 nd application is performed at the interval of 7d, and the application is performed for 2 times. The test is divided into two modes of root irrigation and spray application, and the amount of the medicine liquid is 100mg per granule. The field investigation method adopts a cell to sample at 5 points of a diagonal line, 3 plants are fixedly investigated at each point, the number of all leaves is investigated, and 15 plants are investigated in each cell. The disease condition base is investigated before the application of the 1 st time, the disease condition indexes are investigated 7 days after the application of the 1 st time and 10 days after the application of the 2 nd time, and the dilution times of the aqueous emulsion are respectively 10, 20 and 40 times. According to the disease symptoms, the disease level is recorded according to the format of table 2, the disease index is calculated according to the formula (2), and then the field control effect is calculated according to the formula (3). The disease level and the corresponding symptom of the seedling stage are described in table 2.
TABLE 2 grading Standard of disease conditions
DI＝∑(s×n)/(N×9)×100……………………………………………(2)。
DI-disease index;
s-number of levels of each disease index;
n-number of leaves at each disease index level;
n-survey total leaf number.
Control effect is (control area disease index-treatment area disease index)/control area disease index X100% … … … (3).
3. Results
As can be seen from the field control effects in tables 3 and 4, the 1% eurycomanone aqueous emulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
Table 31% aqueous eurycomanone emulsion control of banana wilt, papaya anthracnose and guava leaf blight (root irrigation)
TABLE 41% aqueous eurycomanone emulsion control of banana vascular wilt, papaya anthracnose and guava leaf blight (spray)
Example 10: preparation of 5% compound 8(eurycomanone) aqueous emulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. Preparing the eurycomanone into an aqueous emulsion, wherein the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 5 percent;
(2) solvent (methanol): 2 percent;
(3) emulsifier (Ningru 130): 2 percent;
(4) co-emulsifier (1-dodecanol): 1 percent;
(5) antifreeze (glycerin): 1 percent;
(6) density modifier (calcium chloride): 0.5 percent;
(7) pH adjuster (phosphoric acid): 0.1 percent;
(8) defoaming agent (octadecyl trimethyl ammonium chloride: 0.1%;
(9) water (deionized water): 88.3 percent.
The preparation method comprises the following steps: mixing the effective components, the solvent, the emulsifier and the co-emulsifier in the components, dissolving the mixture into a uniform oil phase, mixing the rest components into a uniform water phase, and adding the water phase into the oil phase under high-speed stirring to obtain the well-dispersed 5% eurycomanone aqueous emulsion.
2. The prepared 5% eurycomanone aqueous emulsion is used for carrying out field tests on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and the calculation formula are the same as those in example 9, and the difference is that the dilution times of the aqueous emulsion are respectively 50, 100 and 200.
3. Results
As can be seen from the field control effects in tables 5 and 6, the 5% eurycomanone aqueous emulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
Control Effect (root irrigation) of aqueous eurycomanone emulsion (Table 55%) on banana wilt, papaya anthracnose and guava leaf blight
TABLE 65% aqueous eurycomanone emulsion for controlling banana wilt, papaya anthracnose and guava leaf blight (spray)
Example 11: preparation of 10% compound 8(eurycomanone) aqueous emulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. Preparing the eurycomanone into an aqueous emulsion, wherein the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 10 percent;
(2) solvent (methanol): 5 percent;
(3) emulsifier (tween 80): 5 percent;
(4) coemulsifier (1-tetradecanol): 5 percent;
(5) antifreeze (glycerin): 2 percent;
(6) density modifier (calcium chloride): 0.5 percent;
(7) pH adjuster (phosphoric acid): 0.1 percent;
(8) antifoam (octadecyl trimethyl ammonium chloride): 0.1 percent;
(9) water (deionized water): 72.3 percent.
The preparation method comprises the following steps: mixing the effective components, the solvent, the emulsifier and the co-emulsifier in the components, dissolving the mixture into a uniform oil phase, mixing the rest components into a uniform water phase, and adding the water phase into the oil phase under high-speed stirring to obtain the well-dispersed 10% eurycomanone aqueous emulsion.
2. The 10% eurycomanone aqueous emulsion prepared above was used for field experiments on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and calculation formula were the same as example 9, except that the dilution times of the aqueous emulsion were 100, 200 and 400 times, respectively.
3. Results
As can be seen from the field control effects in tables 7 and 8, the 5% eurycomanone aqueous emulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
Control effect of aqueous eurycomanone emulsion (root irrigation) on banana wilt, papaya anthracnose and guava leaf blight in table 710%
TABLE 810% aqueous eurycomanone emulsion for controlling banana wilt, papaya anthracnose and guava leaf blight (spray)
Example 12: preparation of 20% compound 8(eurycomanone) aqueous emulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. Preparing the eurycomanone into an aqueous emulsion, wherein the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 20 percent;
(2) solvent (methanol): 5 percent;
(3) emulsifier (tween 80): 5 percent;
(4) coemulsifier (1-tetradecanol): 5 percent;
(5) antifreeze (glycerin): 2 percent;
(6) density modifier (calcium chloride): 0.5 percent;
(7) pH adjuster (phosphoric acid): 0.1 percent;
(8) antifoam (octadecyl trimethyl ammonium chloride): 0.1 percent;
(9) water (deionized water): 62.3 percent.
The preparation method comprises the following steps: mixing the effective components, the solvent, the emulsifier and the co-emulsifier in the components, dissolving the mixture into a uniform oil phase, mixing the rest components into a uniform water phase, and adding the water phase into the oil phase under high-speed stirring to obtain the well-dispersed 20% eurycomanone aqueous emulsion.
2. The 20% eurycomanone aqueous emulsion prepared above was used for field experiments on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and calculation formula were the same as example 9, except that the dilution times of the aqueous emulsion were 200, 400 and 800 times, respectively.
3. Results
As can be seen from the field control effects in tables 9 and 10, the 5% eurycomanone aqueous emulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
Table 920% aqueous eurycomanone emulsion control of banana wilt, papaya anthracnose and guava leaf blight (root irrigation)
Control Effect (spray) of the aqueous eurycomanone emulsion of Table 1020% on banana vascular wilt, papaya anthracnose and guava leaf blight
Example 13: preparation of 30% compound 8(eurycomanone) microemulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. The eurycomanone is prepared into microemulsion, and the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 30 percent;
(2) solvent (methanol): 10 percent;
(3) emulsifier (farm milk No. 300): 10 percent;
(4) stabilizer (n-butyl glycidyl ether): 3 percent;
(5) antifreeze (ethylene glycol): 5 percent;
(6) water (deionized water): 42 percent.
The preparation method comprises the following steps: mixing the effective components, solvent, emulsifier, stabilizer and antifreezing agent to obtain uniform oil phase, slowly adding deionized water under stirring to obtain water-in-oil emulsion, stirring and heating to quickly convert phase to form oil-in-water type, cooling to room temperature to make it reach balance, and filtering to obtain stable 30% oil-in-water type eurycomanone microemulsion.
2. The 30% eurycomanone microemulsion prepared above was used for field experiments on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and calculation formula were the same as in example 9, except that the dilution times of the microemulsion were 300, 600 and 1200 times, respectively.
3. Results
As can be seen from the field control effects in tables 11 and 12, the 30% eurycomanone microemulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
TABLE 1130% eurycomanone microemulsion has control effect on banana wilt, papaya anthracnose and guava leaf blight (root irrigation)
TABLE 1230% eurycomanone microemulsion for control of banana wilt, papaya anthracnose and guava leaf blight (spray)
Example 14: preparation of 40% compound 8(eurycomanone) microemulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. The eurycomanone is prepared into microemulsion, and the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 40 percent;
(2) solvent (methanol): 10 percent;
(3) emulsifier (sodium diisooctyl succinate): 10 percent;
(4) stabilizer (o-tolyl glycidyl ether): 3 percent;
(5) antifreeze (ethylene glycol): 8 percent;
(6) water (deionized water): 29 percent.
The preparation method comprises the following steps: mixing the effective components, solvent, emulsifier, stabilizer and antifreezing agent to obtain uniform oil phase, slowly adding deionized water under stirring to obtain water-in-oil emulsion, stirring and heating to quickly convert phase to form oil-in-water type, cooling to room temperature to make it reach equilibrium, and filtering to obtain 40% oil-in-water type eurycomanone microemulsion.
2. The field test of banana wilt, papaya anthracnose and guava leaf blight with the prepared 40% eurycomanone microemulsion is the same as that in example 9 except that the dilution times of the microemulsion are 400, 800 and 1600 times.
3. Results
As can be seen from the field control effects in tables 13 and 14, the 40% eurycomanone microemulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
TABLE 1340% eurycomanone microemulsion for controlling banana wilt, papaya anthracnose and guava leaf blight (root irrigation)
Control effect (spray) of table 1440% eurycomanone microemulsion on banana wilt, papaya anthracnose and guava leaf blight
Example 15: preparation of 50% compound 8(eurycomanone) microemulsion and effect thereof in field prevention and control of banana wilt, papaya anthracnose and guava leaf blight
1. The eurycomanone is prepared into microemulsion, and the components and the weight percentage of each component are as follows:
(1) active ingredient (eurycomanone): 50 percent;
(2) solvent (methanol): 10 percent;
(3) emulsifier (sodium diisooctyl succinate): 10 percent;
(4) stabilizer (o-tolyl glycidyl ether): 3 percent;
(5) antifreeze (glycerin): 10 percent;
(6) water (deionized water): 17 percent.
The preparation method comprises the following steps: mixing the effective components, solvent, emulsifier, stabilizer and antifreezing agent to obtain uniform oil phase, slowly adding deionized water under stirring to obtain water-in-oil emulsion, stirring and heating to quickly convert phase to form oil-in-water type, cooling to room temperature to make it reach balance, and filtering to obtain stable 50% oil-in-water type eurycomanone microemulsion.
2. The 50% eurycomanone microemulsion prepared above was used for field experiments on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and calculation formula were the same as in example 9, except that the dilution times of the microemulsion were 500, 1000 and 2000 times, respectively.
3. Results
As can be seen from the field control effects in tables 15 and 16, the 50% eurycomanone microemulsion has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
TABLE 1550% eurycomanone microemulsion for control of banana wilt, papaya anthracnose and guava leaf blight (root irrigation)
TABLE 1650 control of banana vascular wilt, papaya anthracnose and guava leaf blight by the microemulsion of eurycomanone (spray)
Example 16: preparation of 70% compound 8(eurycomanone) dry suspending agent and effect thereof in field control of banana wilt, papaya anthracnose and guava leaf blight
1. The eurycomanone is prepared into a dry suspending agent, and the components and the weight percentage of each component are as follows
(1) Active ingredient (eurycomanone): 70 percent;
(2) dispersant (cottonseed cake protein hydrolysate, 40% solids content): 25 percent;
(3) emulsifier (tween 80): 5 percent.
The preparation process of the cottonseed cake protein hydrolysate in the components comprises the following steps: the weight ratio of the cottonseed cake to the lime to the water is set to be 1:0.2:5, a small amount of water is used for preparing lime milk, the rest water and the lime milk are added into a reaction pot, the reaction pot is heated to boiling, then the cottonseed cake is added and stirred, the cottonseed cake is hydrolyzed for 2 hours under the boiling state, and the water lost due to evaporation is supplemented at any time in the hydrolysis process. Cooling slightly after hydrolysis, neutralizing with hydrochloric acid to pH 8, stirring, heating to boil, filtering to obtain brown red transparent liquid, and concentrating the filtered hydrolysate in a concentrating pot for 5 hr to obtain cottonseed cake protein hydrolysate with solid content of 40%.
Heating the cottonseed cake protein hydrolysate to boiling, adding eurycomanone and Tween 80 under boiling state, stirring to disperse fully, and drying the prepared material at 90 ℃ for 2 minutes to obtain 70% eurycomanone dry suspension.
2. The 70% eurycomanone dry suspending agent prepared above was used for field experiments on banana wilt, papaya anthracnose and guava leaf blight, the experimental design and calculation formula were the same as example 9, except that the dilution times of the dry suspending agent were 700, 1400 and 2800 times, respectively.
3. Results
As can be seen from the field control effects in tables 17 and 18, the 70% eurycomanone dry suspension agent has better control effects on banana vascular wilt, papaya anthracnose and guava leaf blight through root irrigation and leaf surface spraying, but the spraying mode has better effect.
TABLE 1770% Dry suspension of eurycomanone for controlling banana vascular wilt, papaya anthracnose and guava leaf blight (root irrigation)
TABLE 1870% control of banana vascular wilt, papaya anthracnose and guava leaf blight with eurycomanone dry suspension (spray)
As can be seen from examples 9-16, compound 8(eurycomanone) can be prepared into aqueous emulsions, microemulsions and dry suspending agents for controlling banana vascular wilt, papaya anthracnose and guava leaf blight, wherein the best control effect is obtained by spraying 10-fold diluent of 1% eurycomanone aqueous emulsion.
The embodiments of the present invention have been described in detail, but the present invention is not limited to the described embodiments. It will be apparent to those skilled in the art that various changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, and the scope of protection is still within the scope of the invention.
Claims (10)
1. The application of quassinoid compounds in preventing and treating plant fungal diseases is provided.
2. The application of quassinoid compounds in preparing medicaments for preventing and treating plant fungal diseases is provided.
3. The use according to claim 1 or 2, wherein the quassinoids are selected from C represented by the following structural formula19Picrasma quassioides bitter principle compounds and C20At least one of the quassin compounds:
4. use according to claim 3, wherein C is19The quassinoid compound is selected from at least one of the following structural formulas:
said C is20The quassinoid compound is selected from at least one of the following structural formulas:
5. the use according to claim 1 or 2, wherein the plant fungal diseases include but are not limited to banana vascular wilt, papaya anthracnose, guava leaf blight, potato dry rot, apple rot and tomato early blight.
6. A fungicide capable of being transported in a plant body is characterized in that an active ingredient of the fungicide comprises quassinoid compounds.
7. The fungicide according to claim 6, wherein said quassinoid is selected from C represented by the following structural formula19Picrasma quassioides bitter principle compounds and C20At least one of the quassin compounds:
8. according to claim7 the fungicide according to said claim, wherein C is19The quassinoid compound is selected from at least one of the following structural formulas:
said C is20The quassinoid compound is selected from at least one of the following structural formulas:
9. the fungicide according to claim 6, wherein said quassinoid is contained in an amount of 1% to 70% by weight of the fungicide.
10. The fungicide according to claim 6, wherein said fungicide is in the form of emulsion, microemulsion or suspension.
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| CN113975267A (en) * | 2021-10-26 | 2022-01-28 | 广东中诚生物科技有限公司 | Application of 6 alpha-hydroxyureycolatone in preparation of anti-dengue virus drugs |
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| CN109258662A (en) * | 2018-09-28 | 2019-01-25 | 广东省农业科学院果树研究所 | The antifeedant for insect 13,21-dihydroeurycomanone of transporting in plant and application |
| CN109535172A (en) * | 2018-10-19 | 2019-03-29 | 广东省农业科学院果树研究所 | A kind of quassinoids class compound and its preparing the application in antifeedant for insect |
| CN110612981A (en) * | 2019-10-18 | 2019-12-27 | 广东省农业科学院果树研究所 | Application of quassin compounds in killing ants |
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| CN109258662A (en) * | 2018-09-28 | 2019-01-25 | 广东省农业科学院果树研究所 | The antifeedant for insect 13,21-dihydroeurycomanone of transporting in plant and application |
| CN109535172A (en) * | 2018-10-19 | 2019-03-29 | 广东省农业科学院果树研究所 | A kind of quassinoids class compound and its preparing the application in antifeedant for insect |
| CN110612981A (en) * | 2019-10-18 | 2019-12-27 | 广东省农业科学院果树研究所 | Application of quassin compounds in killing ants |
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| CN113975267A (en) * | 2021-10-26 | 2022-01-28 | 广东中诚生物科技有限公司 | Application of 6 alpha-hydroxyureycolatone in preparation of anti-dengue virus drugs |
| CN113975267B (en) * | 2021-10-26 | 2023-11-28 | 广东中诚生物科技有限公司 | Application of 6 alpha-hydroxyeyeurycommactone in preparation of anti-dengue virus drugs |
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