CN108477170B - Quinoline compound, preparation method thereof and application thereof in preventing and treating plant diseases - Google Patents
Quinoline compound, preparation method thereof and application thereof in preventing and treating 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Abstract
The invention discloses a quinoline compound, a preparation method thereof and application thereof in preventing and treating plant diseases. The test result shows that: the compounds have excellent control effects on plant diseases caused by cotton fusarium wilt, wheat gibberella, sclerotinia sclerotiorum, rhizoctonia solani and rice blast and on powdery mildew of pumpkin and cucumber. The invention has simple preparation process, cheap and easily obtained raw materials and high product purity, and is expected to be developed into a new bactericide.
Description
Technical Field
The invention belongs to the field of natural medicinal chemistry and the technical field of pesticides, discloses a new application of a quinoline derivative, and particularly relates to a quinoline derivative for preventing and treating plant diseases caused by cotton Fusarium oxysporum f.sp.vasifenum (Atk.) Snyder & Hansen), wheat gibberellin (Fusarium graminearum), sclerotinia sclerotiorum (sclerotinia sclerotiorum), Rhizoctonia solani (Rhizoctonia solani) and rice blast (Magnaporthe oryzae) and field control effects on powdery mildew of pumpkin and cucumber powdery mildew.
Background
At present, plant diseases caused by fungi are mainly controlled by chemistry, and although many commercial bactericides have good control effect at present, the problem of '3R' (residual, resistance to resistance and resurgence) is getting worse and worse due to the wide use of the chemical pesticides, and the plant diseases have attracted great attention of society. Therefore, research and development of efficient and safe pesticides for controlling plant diseases have become important subjects for plant protection workers and are a necessary way for sustainable development of agricultural production, and plant-derived pesticides, as part of biogenic pesticides, are favored by researchers because of their advantages of low toxicity, no residue, high selectivity, easy decomposition, difficulty in pest resistance generation, and the like. Therefore, searching and screening potential bactericidal secondary metabolites from plant resources, and taking the bactericidal secondary metabolites as a lead structure to carry out structure optimization design is becoming one of important ways for creating novel bactericides.
Quinine is a well-known alkaloid natural drug, commonly known as Cinchona alkaloid, and was first extracted from the bark of the rubiaceae family plant Cinchona tree (Cinchona hedgeriana (Howard) Moens ex Trim) and its congeners. Quinine is a specific drug for the treatment of malaria, and its discovery and use has saved the lives of countless malaria patients. The prophase of a subject group discovers that quinine has the inhibition activity of 69.58% on sclerotinia sclerotiorum under 50ppm, and further performs activity test evaluation on a similarity molecule mefloquine (antimalarial drug) to discover that the antibacterial activity of the quinine is obviously improved. According to the activity screening result, the quinoline compound is used as a mother nucleus lead structure and is subjected to derivative synthesis at the 4 th position to synthesize a series of new quinoline compounds, so that the bactericidal activity of the quinoline compound is remarkably improved, the quinoline compound is simpler and more economical in the synthesis method, and the synthesis cost is remarkably reduced. Although more researches on quinine are reported, no literature report is reported on the application of quinine in inhibiting agricultural germs at present.
The invention takes quinine as a clue, designs and synthesizes a series of new molecules through structure optimization and derivative synthesis, finds that the target compound has better antibacterial effect on cotton wilt pathogen, wheat gibberella, sclerotinia sclerotiorum, rhizoctonia solani and rice blast pathogen, finds that the target compound has better control effect on pumpkin powdery mildew and cucumber powdery mildew through field test, and can be used as a novel broad-spectrum bactericide.
Disclosure of Invention
The invention provides a technical method for preparing a medicament against cotton wilt pathogen, wheat scab pathogen, sclerotinia sclerotiorum, rhizoctonia solani and rice blast pathogen, which contains quinoline derivatives (shown in figure-2) shown by any compound of K L-1-K L-26 with effective treatment amount.
The quinoline derivatives are obtained by conventional methods such as silica gel column chromatography for many times, and pure products are obtained by separation, and the quinoline compounds K L-1-K L-26 are determined by spectrum techniques such as mass spectrum and nuclear magnetic resonance, the structural formula of the quinoline compounds is shown in figure 2.
Drawings
FIG. 1 Process for Compound discovery and optimization
FIG. 2 quinoline derivatives
Detailed Description
Example 1
Synthesis of quinoline derivative (K L-1)
The method comprises the following steps:
the second method comprises the following steps:
the specific synthesis operation is as follows:
the first method comprises the steps of adding 0.247 g of raw material 2, 8-bis (trifluoromethyl) quinoline into a 50m L single-neck bottle, dissolving the raw material in 20m L of acetone, adding equimolar potassium carbonate, adding equimolar benzyl chloroformate, heating and refluxing for 3 hours, filtering to obtain a filtrate, evaporating the solvent, and purifying a developing agent (ethyl acetate: petroleum ether: 1:5) by column chromatography to obtain a white solid.
Method II comprises the steps of adding 0.247 g of raw material 2, 8-bis (trifluoromethyl) quinoline into a 50m L single-neck bottle, adding 5m L of acetic anhydride, heating and refluxing for 3h, performing plate chromatography to track the completion of the reaction, evaporating excessive acetic anhydride under reduced pressure, and performing plate chromatography to separate (developing solvent: ethyl acetate: petroleum ether: 1:5) to obtain a white solid.
K L-1 white solid, yield 85%;1H NMR(400MHz,Chloroform-d)8.23(dd,J＝17.4,7.9Hz,2H),7.80(s,1H),7.75(t,J＝7.9Hz,1H),2.17(s,3H).ESI-MS m/z:346.06[M+Na]+.
example 2
Synthesis of K L-2 Experimental procedure as in example 1, acetyl chloride was changed to propionyl chloride.
K L-2 white solid, yield 83%;1H NMR(400MHz,Chloroform-d)8.15(dd,J＝14.6,7.9Hz,2H),7.74(s,1H),7.67(s,1H),2.77(d,J＝7.5Hz,2H),1.32(t,J＝7.6Hz,3H).ESI-MS m/z:360.08[M+Na]+.
example 3
Synthesis of K L-3 Experimental procedure as in example 1, acetyl chloride was exchanged for chloroacetyl chloride.
K L-3 white solid, yield 72%;1H NMR(400MHz,Chloroform-d)8.19(dd,J＝20.8,7.9Hz,2H),7.79(s,1H),7.72(t,J＝7.9Hz,1H),4.43(s,2H).ESI-MS m/z:380.02[M+Na]+.
example 4
Synthesis of K L-4 Experimental procedure as in example 1, acetyl chloride was exchanged for n-butyryl chloride.
K L-4 white solid, yield 84%;1H NMR(400MHz,Chloroform-d)8.16(s,2H),7.73(s,1H),7.68(s,1H),2.71(t,J＝7.4Hz,2H),1.90–1.75(m,2H),1.06(t,J＝7.4Hz,3H).ESI-MSm/z:374.09[M+Na]+.
example 5
Synthesis of K L-5 Experimental procedure as in example 1, acetyl chloride was changed to n-valeryl chloride.
K L-5, white solid, yield 88%;1H NMR(400MHz,Chloroform-d)8.20–8.10(m,2H),7.72(s,1H),7.68(s,1H),2.73(t,J＝7.5Hz,2H),1.79(t,J＝7.5Hz,2H),1.48–1.40(m,2H),0.96(t,J＝7.3Hz,3H).ESI-MS m/z:388.11[M+Na]+.
example 6
Synthesis of K L-6 Experimental procedure as in example 1, acetyl chloride was exchanged for isovaleryl chloride.
K L-6 white solid, yield 89%;1H NMR(400MHz,Chloroform-d)8.15(dd,J＝14.8,7.9Hz,2H),7.72(s,1H),7.67(t,J＝7.9Hz,1H),2.60(d,J＝7.1Hz,2H),2.34–2.22(m,1H),1.07(d,J＝6.6Hz,6H).ESI-MS m/z:388.11[M+Na]+.
example 7
Synthesis of K L-7 Experimental procedure as in example 1 was carried out by converting acetyl chloride to n-hexanoyl chloride.
K L-7 white solid, yield 86%;1H NMR(400MHz,Chloroform-d)8.15(dd,J＝13.0,7.9Hz,2H),7.73(s,1H),7.67(t,J＝7.9Hz,1H),2.72(t,J＝7.5Hz,2H),1.80(p,J＝7.4Hz,2H),1.47–1.29(m,4H),0.90(t,J＝6.9Hz,3H).ESI-MS m/z:402.13[M+Na]+..
example 8:
synthesis of K L-8 Experimental procedure as in example 1, acetyl chloride was changed to benzoyl chloride.
K L-8 white solid, yield 84%;1H NMR(400MHz,Chloroform-d)8.24(d,J＝7.5Hz,2H),8.14(d,J＝7.3Hz,1H),8.12–8.00(m,1H),7.83(s,1H),7.68(td,J＝7.8,4.7Hz,2H),7.54(t,J＝7.7Hz,2H).ESI-MS m/z:408.09[M+Na]+..
example 9
Synthesis of K L-9 Experimental procedure as in example 1, acetyl chloride was converted to phenyl chloroformate.
K L-9 white solid, yield 80%;1H NMR(400MHz,Chloroform-d)8.40(d,J＝8.5Hz,1H),8.18(d,J＝7.3Hz,1H),8.00(s,1H),7.75(t,J＝7.9Hz,1H),7.46–7.38(m,2H),7.38–7.32(m,1H),7.30–7.27(m,2H).ESI-MS m/z:441.57[M+K]+.
example 10
Synthesis of K L-10 Experimental procedure as in example 1 was carried out by converting acetyl chloride to benzyl chloroformate.
K L-10 white solid, yield 88%;1H NMR(400MHz,Chloroform-d)8.26(dd,J＝8.4,1.4Hz,1H),8.13(d,J＝7.2Hz,1H),7.89(s,1H),7.67(t,J＝7.9Hz,1H),7.42(dq,J＝4.5,2.5Hz,2H),7.40–7.35(m,3H),5.32(s,2H).ESI-MS m/z:438.08[M+Na]+..
example 11
Synthesis of K L-11 Experimental procedure as in example 1, acetyl chloride was exchanged for methanesulfonyl chloride.
K L-11 white solid, yield 74%;1H NMR(400MHz,Chloroform-d)8.33(d,J＝8.5Hz,1H),8.19(d,J＝7.3Hz,1H),7.80(s,1H),7.76(s,1H),3.36(s,3H).ESI-MS m/z:360.06[M+H]+.
example 12
Synthesis of K L-12 Experimental procedure as in example 1, acetyl chloride was exchanged for phenylmethanesulfonyl chloride.
K L-12 white solid, yield 79%;1H NMR(400MHz,Chloroform-d)8.14–8.07(m,2H),7.93–7.87(m,2H),7.69(td,J＝7.4,1.4Hz,1H),7.62(t,J＝7.9Hz,1H),7.57–7.50(m,3H).ESI-MSm/z:444.06[M+Na]+..
example 13
Synthesis of K L-13 Experimental procedure as in example 1, acetyl chloride was exchanged for tert-butyldimethylsilyl chloride.
K L-13 white solid, 50% yield;1H NMR(400MHz,Chloroform-d)8.13(d,J＝7.3Hz,1H),8.04(d,J＝7.6Hz,1H),7.54(t,J＝7.9Hz,1H),6.77–6.69(m,1H),1.10(s,9H),0.40(s,2H).ESI-MS m/z:418.13[M+Na]+.
example 14
Synthesis of K L-14 Experimental procedure as in example 1 was carried out by replacing acetyl chloride with 1-chloropropionyl chloride.
K L-14 white solid, yield 82%;1H NMR(400MHz,Chloroform-d)8.21(d,J＝8.6Hz,1H),8.15(d,J＝7.3Hz,1H),7.76–7.67(m,2H),3.91(t,J＝6.3Hz,2H),3.22(t,J＝6.3Hz,2H).
ESI-MS m/z:409.98[M+K]+.
example 15
Synthesis of K L-15 Experimental procedure as in example 1 was carried out by replacing acetyl chloride with 2-chloropropionyl chloride.
K L-15 white solid, yield 34%;1H NMR(400MHz,Chloroform-d)8.52(d,J＝8.5Hz,1H),8.14(d,J＝7.3Hz,1H),7.65(t,J＝7.8Hz,1H),7.31(s,1H),4.12(s,1H),1.58(s,3H).ESI-MSm/z:494.00[M+Na]+.
example 16
Synthesis of K L-16 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for 1-chloro-n-butyryl chloride.
K L-16 white solid, yield 68%;1H NMR(400MHz,Chloroform-d)8.28–8.18(m,2H),7.81(s,1H),7.76(s,1H),3.74(t,J＝6.1Hz,2H),3.04(t,J＝7.2Hz,2H),2.43–2.24(m,2H).ESI-MSm/z:408.02[M+Na]+.
example 17
Synthesis of K L-17 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for 1-chloro-n-valeryl chloride.
K L-17 white solid, yield 70%;1H NMR(400MHz,Chloroform-d)8.26–8.18(m,2H),7.80(s,1H),7.75(t,J＝7.9Hz,1H),3.65(t,J＝6.0Hz,2H),2.86(t,J＝7.1Hz,2H),2.16–1.86(m,4H).ESI-MS m/z:422.07[M+Na]+.
example 18
Synthesis of K L-18 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for isobutyryl chloride.
K L-18 white solid, yield 83%;1H NMR(400MHz,Chloroform-d)8.21(t,J＝8.2Hz,2H),7.78(s,1H),7.75(t,J＝8.4Hz,1H),1.47(d,J＝7.0Hz,6H).ESI-MS m/z:374.09[M+Na]+.
example 19
Synthesis of K L-19 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for 2-bromopropionyl chloride.
K L-19 white solid, yield 45%;1H NMR(400MHz,Chloroform-d)8.60(d,J＝8.1Hz,1H),8.02(d,J＝7.5Hz,1H),7.52(t,J＝7.9Hz,1H),6.69(d,J＝1.9Hz,1H),4.87–4.74(m,2H),2.06(d,J＝6.9Hz,3H).ESI-MS m/z:388.11[M+Na]+.
example 20
Synthesis of K L-20 Experimental procedure as in example 1, acetyl chloride was exchanged for chloro pivaloyl chloride.
K L-20 white solid, yield 75%;1H NMR(400MHz,Chloroform-d)8.28(dd,J＝8.5,1.3Hz,1H),8.21(d,J＝7.3Hz,1H),7.77(d,J＝7.9Hz,1H),7.70(s,1H),3.86(s,2H),1.60(s,6H).
ESI-MS m/z:422.07[M+Na]+.
example 21
Synthesis of K L-21 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for isobutyryl chloride.
K L-21 white solid, yield 78%;1H NMR(400MHz,Chloroform-d)8.21(s,1H),8.19(s,1H),7.78–7.71(m,2H),1.51(s,9H).ESI-MS m/z:388.11[M+Na]+.
example 22
Synthesis of K L-22 Experimental procedure as in example 1, acetyl chloride was exchanged for propionyl chloride.
K L-22 white solid, yield 75%;1H NMR(400MHz,Chloroform-d)8.20(d,J＝8.5Hz,1H),8.13(d,J＝7.3Hz,1H),7.72(s,1H),7.69(d,J＝7.9Hz,1H),1.99(tt,J＝7.9,4.6Hz,1H),1.30–1.22(m,2H),1.23–1.09(m,2H).ESI-MS m/z:372.07[M+Na]+.
example 23
Synthesis of K L-23 Experimental procedure as in example 1 was carried out to convert acetyl chloride to butyryl chloride.
K L-23 white solid, 73% yield;1H NMR(400MHz,Chloroform-d)8.21(dd,J＝7.7,5.4Hz,2H),7.80(s,1H),7.74(s,1H),3.62(p,J＝8.5Hz,1H),2.71–2.37(m,4H),2.32–2.00(m,2H).ESI-MS m/z:386.09[M+Na]+.
example 24
Synthesis of K L-24 Experimental procedure as in example 1 was carried out to exchange acetyl chloride for cyclopentanoyl chloride.
K L-24 white solid, yield 68%;1H NMR(400MHz,Chloroform-d)8.22(dd,J＝13.5,7.9Hz,2H),7.78(s,1H),7.74(s,1H),3.22(p,J＝8.0Hz,1H),2.21–2.13(m,3H),2.11–2.02(m,1H),1.89–1.82(m,2H),1.81–1.71(m,2H).ESI-MS m/z:400.11[M+Na]+.
example 25
Synthesis of K L-25 Experimental procedure as in example 1 was used to convert acetyl chloride to cyclohexanoyl chloride.
K L-25 white solid, yield 76%；1H NMR(400MHz,Chloroform-d)8.18–8.10(m,2H),7.69(s,1H),7.66(d,J＝7.9Hz,1H),2.72(tt,J＝11.3,3.7Hz,1H),2.20–2.07(m,2H),1.83(dt,J＝12.9,3.6Hz,2H),1.76–1.54(m,3H),1.33(dtdd,J＝29.2,17.0,7.7,4.4Hz,3H).ESI-MS m/z:414.13[M+Na]+.
Example 26
Synthesis of K L-26 Experimental procedure as in example 1, acetyl chloride was exchanged for methacryloyl chloride.
K L-26 white solid, yield 82%;1H NMR(400MHz,Chloroform-d)8.22(dd,J＝11.6,7.9Hz,2H),7.82(s,1H),7.75(s,1H),6.57(s,1H),6.09–5.92(m,1H),2.18(t,J＝1.3Hz,3H).ESI-MSm/z:372.08[M+Na]+.
example 27
Indoor bacteriostatic activity determination and result
1) Experimental materials:
quinoline derivatives with chemical formulas K L-1-K L-26 are synthesized in the laboratory.
The plant pathogenic bacteria used in the experiment are strains stored at 4 ℃ in a laboratory, and the adopted culture medium is a potato culture medium (PDA for short).
The PDA culture medium comprises potato (peeled) 200g, glucose 20g, agar 15g, tap water 1000m L, and natural pH.
The preparation method comprises cleaning rhizoma Solani Tuber osi, peeling, weighing 200g, cutting into small pieces, adding water, boiling (boiling for 20-30 min, and breaking with glass rod), filtering with eight layers of gauze, adding agar 15-20g according to experiment requirement, adding glucose 20g, stirring, dissolving completely, cooling slightly to 1000m L, packaging, sterilizing at 121 deg.C for 20 min, and cooling.
2) Experimental methods
A growth rate method is used.
1. Firstly, 5 plant pathogenic bacteria are cultured on a PDA plate at 25 ℃ for about 6 days for later use.
2. Heating PDA culture medium to melt, cooling to 45-50 deg.C, adding quinoline derivatives with different concentrations to obtain culture medium containing 50, 25, 10, 5 and 2.5 μ g/m L medicinal liquid, and respectively pouring into culture dish for cooling.
3. According to the sterile operation procedure, a round fungus cake (the diameter is 0.50cm) is punched at the edge of each strain hypha cultured for 6d (the growth condition is consistent as much as possible) by a puncher, then an inoculating needle is used for picking the round fungus cake to the center of a drug-containing flat plate, and then the culture dish is placed in an incubator (25 ℃) for culture.
4. Observing and measuring the growth condition of hyphae at different time after treatment, measuring the diameter by adopting a cross method, processing data and calculating the inhibition rate.
5. Inhibition ratio (%) - (control hypha diameter-treated hypha diameter)/control hypha diameter × 100
6. Each treatment was repeated 3 times.
3) Quinoline derivatives have antibacterial effect on the growth of cotton fusarium wilt, wheat fusarium graminearum, sclerotinia sclerotiorum, rhizoctonia solani and rice blast hypha
The indoor biological activity measurement is carried out by the aid of a growth rate method according to a standard biological test method NY/T1156.2-2006 for cotton fusarium wilt, wheat fusarium graminearum, sclerotinia sclerotiorum, rhizoctonia solani and rice blast bacteria, the inhibitory activity of quinoline derivatives K L-1-K L-26 on the five bacteria is determined, and a table 1 shows the inhibitory activity test result of the quinoline derivatives on the growth of hyphae of cotton fusarium wilt, wheat fusarium graminearum, sclerotinia sclerotiorum, rhizoctonia solani and rice blast bacteria.
TABLE 1 inhibition activity test results of quinoline derivatives against the growth of cotton fusarium oxysporum, wheat fusarium graminearum, sclerotinia sclerotiorum, rhizoctonia solani and rice blast
Note that three replicates were used for each treatment in the experiment, the data in the table are the average of the three replicates, and "-" indicates that no bacteriostatic experiments were performed.
Example 28
Evaluating the field control effect of the cucurbita pepo powdery mildew and the cucumber powdery mildew.
1) Powdery mildew of pumpkin
1. Experimental materials: zucchini, variety 'Qiangqiang'. Sphaerotheca fuliginea (Schl.) poll.) is obtained from a source of free-living bacteria from a potted Cucurbita pepo in a greenhouse of the academy of agricultural sciences of Gansu province.
2. The contrast and test reagents comprise propiconazole, myclobutanil, propiconazole and K L-1 compound.
3. The experimental process comprises the following steps:
(1) the disease and pest control before the cultivation management test field seeding, the fertilizer and water management and the test stage is consistent with the local production. 1 time of
Other pesticides which have influence on powdery mildew are not applied within 10 days before application.
(2) The inoculation method comprises the following steps: 9 and 16 months in 2017, mashing and filtering the fresh leaves with powdery mildew of pumpkin, and suspending the spore in the west
The front of the gourd leaves is evenly sprayed to inoculate bacteria.
(3) The preparation is prepared by diluting 1 concentration of 1500 times solution with 15% K L-1 emulsifiable solution and 12.5% myclobutanil as contrast agent
Oil and 25% propiconazole missible oil are diluted into 1500 times of liquid with 1 concentration, and clear water is additionally arranged for comparison.
(4) The application method comprises the following steps: the medicine is applied 48 hours after the inoculation of 18 days in 2017 and 9 months. The preparation is administered 1 time and 3 times every 7 days (9 months, 18 days, 9 months, 25 days, 10 months, 3 days).
(5) The investigation method comprises the following steps: disease index was investigated 18 days (10 months and 21 days) after the last 1 application, and control effect was calculated. Simultaneous survey
And (4) safety. The disease severity grading standard is as follows:
grade 0-no lesion;
grade 1-the lesion area accounts for less than 2% of the leaf area;
7-the lesion area accounts for 21% -40% of the leaf area;
grade 9-the lesion area accounts for more than 40% of the leaf area.
(6) Controlling effect
(7) Safety evaluation of propiconazole 1500-fold liquid, thickening and hardening of leaves, darkening and greening of color, shortening of petioles and deterioration of growth
The myclobutanil phytotoxicity symptom is similar to propiconazole, but the manifestation is light, K L-1 is safe, and the leaves have no abnormal change.
2) Powdery mildew of cucumber
1. Experimental materials: the cucumber is Sinomei Siberian cocklebur. Cucumber powdery mildew (Sphaerotheca fuliginea) is collected from a self-growing bacterial source on greenhouse potted cucumbers in agricultural academy of sciences in Gansu province.
2. Contrast and test reagents comprise myclobutanil, propiconazole, tebuconazole, difenoconazole and K L-1 compound.
3. The experimental process comprises the following steps:
(1) the disease and pest control before the cultivation management test field seeding, the fertilizer and water management and the test stage is consistent with the local production. Other pesticides which have influence on cucumber powdery mildew are not applied within 10 days before 1 pesticide application.
(2) The inoculation method is that in 2017, 10 months and 7 days, fresh leaves with powdery mildew of cucumber are mashed and filtered, and spore suspension is uniformly sprayed on the front surfaces of the leaves of the cucumber for inoculation.
(3) The preparation is prepared from 15% K L-1 emulsifiable concentrate, 12.5% myclobutanil emulsifiable concentrate, 25% propiconazole emulsifiable concentrate, 430 g/L tebuconazole suspending agent and 25% difenoconazole emulsifiable concentrate, wherein 1 concentration (preparation dosage) of 2500 times diluted solution is set, and clear water is additionally used for comparison.
(4) The application method comprises the steps of pot-planting the cucumber in a greenhouse, starting application of the first application of the powdery mildew at the flowering stage of the cucumber in 10-month and 9-day (natural occurrence, average disease index: 0-level 56, 1-level 35, 3-level 4, 7-level 1 and disease index 6.25), applying the first application of the second application of the first.
(5) Investigation method disease index was investigated 10 days (11 months and 22 days) after the last 1 application of the drug, and the control effect was calculated. While simultaneously investigating security. The disease severity grading standard is as follows:
grade 0-no lesion;
grade 1-the lesion area accounts for less than 2% of the leaf area;
7-the lesion area accounts for 21% -40% of the leaf area;
grade 9-the lesion area accounts for more than 40% of the leaf area.
(6) Controlling effect
(7) Safety evaluation propiconazole application leaves are thickened and hardened, the color is darkened, the petiole is shortened, and the leaf margin is not yellowed, tebuconazole and myclobutanil application leaves are thickened and hardened, the color is darkened, the petiole is shortened, and the leaf margin is yellowed, difenoconazole is safe, K L-1 application plants are curled under the leaf margin of the heart and the leaf, irregular white spots are caused, and the symptoms are light.
Claims (1)
1. The application of the quinoline compound in preventing and treating plant diseases is characterized in that:
the plant diseases are caused by the following pathogenic bacteria: one or more of cotton fusarium wilt, wheat gibberella, sclerotinia sclerotiorum, rhizoctonia solani, rice blast, pumpkin powdery mildew and cucumber powdery mildew.
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| CN110938034B (en) * | 2018-09-21 | 2021-05-11 | 东莞市东阳光农药研发有限公司 | Quinoline derivatives and their use in agriculture |
| CN109467533A (en) * | 2018-12-14 | 2019-03-15 | 兰州大学 | A kind of 8-hydroxyquinoline class compound and preparation method thereof and the purposes in prevention and treatment agricultural disease |
| CN110156678A (en) * | 2019-05-27 | 2019-08-23 | 兰州大学 | A kind of purposes of the derivatives of bis- (trifluoromethyl) the quinolines 4- modifications of 2,8- in controlling plant diseases |
| CN110437146A (en) * | 2019-07-17 | 2019-11-12 | 兰州大学 | A kind of preparation of quinoline 4- hydroxy methacrylates class compound and its application in controlling plant diseases |
| CN112493244A (en) * | 2019-09-16 | 2021-03-16 | 兰州大学 | Application of quinoline 2-position derivative in preparation of agricultural plant disease prevention and treatment medicines |
| CN112939942B (en) * | 2020-12-24 | 2023-11-07 | 聊城大学 | Heterocyclic ester compound containing quinoline structure, and preparation method and application thereof |
| CN112608275A (en) * | 2020-12-29 | 2021-04-06 | 兰州大学 | Application of 2, 8-bis (trifluoromethyl) -4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases |
| CN114957116A (en) * | 2022-07-01 | 2022-08-30 | 浙江工业大学 | 2, 3-dimethyl-8-fluoroquinoline-4-ester compound and preparation method and application thereof |
| CN115466212B (en) * | 2022-10-26 | 2023-09-22 | 河南农业大学 | 2-trifluoromethyl quinoline compound and synthetic method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105994314A (en) * | 2016-07-13 | 2016-10-12 | 兰州大学 | Application of Luotonin A to prevention and treatment of aphid |
| CN107711855A (en) * | 2017-09-11 | 2018-02-23 | 兰州大学 | Application of the peaceful alkali A derivatives of camel in the medicine of preventing and treating or anti-plant disease is prepared |
-
2018
- 2018-03-30 CN CN201810291712.1A patent/CN108477170B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105994314A (en) * | 2016-07-13 | 2016-10-12 | 兰州大学 | Application of Luotonin A to prevention and treatment of aphid |
| CN107711855A (en) * | 2017-09-11 | 2018-02-23 | 兰州大学 | Application of the peaceful alkali A derivatives of camel in the medicine of preventing and treating or anti-plant disease is prepared |
Non-Patent Citations (3)
| Title |
|---|
| Biologically active q uinoline and quinazoline alkaloids part I;Xiao-Fei Shang等;《Medicinal Research Reviews》;20170913;全文 * |
| Biologically active q uinoline and quinazoline alkaloids part II;Xiao-Fei Shang等;《Medicinal Research Reviews》;20180227;全文 * |
| Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives;Ye-Feng Fan等;《Chinese Chemical Letters》;20141104;全文 * |
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