CN108658924B - Application of nucleatum penicillin as agricultural bactericide - Google Patents

Application of nucleatum penicillin as agricultural bactericide Download PDF

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CN108658924B
CN108658924B CN201710191284.0A CN201710191284A CN108658924B CN 108658924 B CN108658924 B CN 108658924B CN 201710191284 A CN201710191284 A CN 201710191284A CN 108658924 B CN108658924 B CN 108658924B
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rot
blight
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anthracnose
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CN108658924A (en
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魏美燕
邵长伦
王长云
王翠芳
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Ocean University of China
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/76—Benzo[c]pyrans
    • 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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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

The invention provides an agricultural bactericide, which is characterized in that a nucleus is usedPlecillin or its salt as effective component for preventing and treating sclerotinia sclerotiorumSclerotinia sclerotiorumWheat snow mold leaf blightMonographella nivalisShell of gaeumannomyces graminisGaeumannomyces graminisSeptoria tritici (Miq.) KuntzeSeptoria triticiAnthracnose of melonGlomerella lagenariumMycosphaerella arachidicola (berk.) kuhnMycosphaerella arachidisAnd downy mildewPlasmopara viticolaCausing agricultural diseases.

Description

Application of nucleatum penicillin as agricultural bactericide
Technical Field
The invention relates to the field of agriculture, in particular to application of a Pleurotus citrinopileatus compound as an agricultural bactericide.
Background
Fungal pathogenic diseases are one of the natural disasters that seriously jeopardize agricultural production, causing huge losses to agricultural production, whereby crops worldwide are reduced in production by about 500 Mt per year on average. Fungal pathogenic diseases can not only cause the reduction of crop yield, but also seriously threaten the quality safety of agricultural products and the international trade thereof. For example, Sclerotinia sclerotiorum (A), (B), (C), C, and CSclerotinia sclerotiorum) Is a worldwide important plant pathogenic bacterium which harms crops and vegetables. It can infect a wide range of monocotyledonous and dicotyledonous plants; wheat snow mold leaf blight: (Monographella nivalis) The seedling can be damaged from the seedling stage to the grain filling stage, and the symptoms such as bud rot, leaf rot, sheath rot, ear rot and the like can be caused, wherein the leaf rot is taken as the main symptom; shell of gaeumannomyces graminis (C)Gaeumannomyces graminis) And septoria tritici (Septoria tritici) Causing severe decrease in wheat yield, cucurbit anthracnose: (Glomerella lagenarium) Damage to melons; mycosphaerella arachidicola (A. arachidis hypogaea)Mycosphaerella arachidis) The yield of the peanuts is reduced; from Peronospora species (Plasmopara viticola) Is an important disease in grape production, and the disease is seriously spread in recent years, so that the diseased leaves are scorched and early fallen, and the growth vigor, the quality and the yield are influenced. More seriously, these agricultural pathogens also cause serious damage to other crops, such as tomatoes, cucumbers, sugar cane, soybeans, etc. The bactericide is an economic and effective method for preventing and treating agricultural diseases, and the current bactericide mainly comprises triazoles, amides, pyrimidinamines, strobilurins and the like. However, the excessive use of the bactericide brings about a series of problems, such as harm of the toxicity of the bactericide to human beings, increase of bactericide residue caused by drug resistance, rampant disease and the like, so that the urgent need for the development of the bactericideHigh-efficiency, low-toxicity, low-residue and environment-friendly bactericide. The special environments of high salt, high pressure, low temperature, oligotrophism, low illumination and the like of the ocean enable the ocean microorganisms to generate a large amount of secondary metabolites with novel structures and unique activities, wherein some compounds have bactericidal activity; and the marine microorganisms can be fermented in a large scale without being limited by resources, thereby providing an important source for developing agricultural bactericides. At present, no bactericide aiming at agricultural pathogenic fungi which is successfully developed from marine microorganisms is found.
The document Shu-Wei Yang, Tze-Ming Chan, Joseph Terracciano1, et al.Journal of Antibiotics(2009) 62, 401-403 disclose that compounds Sch 1385568 inhibit Saccharomyces cerevisiaeSaccharomyces cerevisiaeActivity of (a); the literature Somdej Kanokmedhakul, Kwanjai Kanokmedhakul, Pitak Nasomjai, et al.Journal of Natural Products2006, 69, 891-895 discloses the inhibitory activity of a series of azophilic compounds against candida albicans;
the activity of the natural product Sclerorin compound described by the invention on agricultural pathogenic bacteria is not reported, although a Master thesis 'Synthesis of Sclerotiorin derivatives and bactericidal activity research' discloses the antibacterial activity of the Sclerotiorin derivatives; similar to the present study, but the agricultural pathogens studied by the present invention are not the same as the pathogens in the paper. The activity of the compound on the researched agricultural pathogenic bacteria is obviously stronger than that reported in the literature, the structure of the compound is stable, and the defects of light instability, acid-base sensitivity and the like of the compound reported in the literature are overcome.
Disclosure of Invention
The object of the present invention is to provide a process for the preparation of penicillin derived from marine fungi and its use as an agricultural fungicide, which meets the above-mentioned needs of the prior art. Strain preservation information: the name of the depository: china general microbiological culture Collection center; the address of the depository: the institute of microbiology, national academy of sciences No. 3, Xilu No. 1, Beijing, Chaoyang, Beijing; the preservation date is as follows: 4 months and 3 days in 2014; the preservation number is: CGMCC No. 8994; and (3) classification and naming: penicillium mouldPenicillium sp.
The invention provides application of a compound shown in formula I, and a tautomer, a stereoisomer, a racemate, a nonequivalent mixture of enantiomers, a geometrical isomer, a solvate, a pharmaceutically acceptable salt or a solvate of the salt thereof in preparing agricultural pesticides, wherein the compound shown in formula I has the following structure:
Figure DEST_PATH_IMAGE001
。
the invention obtains the Pleurotus citrinopileatus from the marine fungi, has inhibitory activity on various agricultural pathogenic fungi, can be used as an agricultural bactericide, and has wide application prospect.
In another embodiment of the present invention, there is provided an agricultural fungicide characterized by comprising a compound of formula i or a pharmaceutically acceptable salt thereof as an active ingredient.
The term "pharmaceutically acceptable salts" according to the present invention refers to non-toxic inorganic or organic acid and/or base addition salts. See, e.g., "Salt selection for basic drugs", int. J. pharm. 1986, 33, 201-.
The application of the rosette penicillin as an agricultural bactericide.
The examples of diseases mentioned below are intended only to illustrate the invention, but in no way limit it.
The compounds of formula I are useful for the control of the following diseases: oomycete diseases such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, Chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, Chinese cabbage white rust), damping-off (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (hot pepper rot, loofah sponge rot, wax gourd blight), epidemic diseases (broad bean blight, cucumber blight, pumpkin blight, melon blight, hot pepper, leek blight, garlic blight, cotton blight, tomato blight, etc.; fungi imperfecti diseases such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, bean wilt, cucumber wilt, pumpkin wilt, winter melon wilt, watermelon wilt, sweet melon wilt, hot pepper wilt, broad bean wilt, rape wilt, soybean wilt), root rot (hot pepper root rot, eggplant root rot, bean rot, cucumber root rot, bitter gourd root rot, cotton black root rot, broad bean root rot), damping off (seedling blight of cotton, sesame seedling blight, hot pepper seedling blight, cucumber damping off, cabbage stalk rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry leaf, hot pepper, bean disease, cucumber anthracnose, red sesame anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, eggplant disease, hot pepper anthracnose, vegetable bean disease, and cucumber blight, Balsam pear anthracnose, pumpkin anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, hot pepper verticillium wilt, eggplant verticillium wilt), scab (pumpkin scab, wax gourd scab, melon scab), gray mold (boll gray mold, red ramie gray mold, tomato gray mold, hot pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot (flax brown spot, rape black spot, sesame black spot, sunflower black spot, castor black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato black spot, tomato, Pepper black spot, eggplant black spot, bean black spot, cucumber black spot, celery black spot, carrot black rot, carrot black spot, apple black spot, peanut black spot), spot blight (tomato spot blight, pepper spot blight, celery spot blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (tomato stem base rot, bean stem base rot), and others (corn round spot, kenaf waist fold, rice blast, black sheath blight, sugarcane eye spot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black spot, melon big spot, peanut net spot, tea leaf spot, red leaf spot, black leaf spot, peanut net spot, tea leaf spot, tomato black spot, potato leaf spot, potato black spot, tomato leaf spot, etc, Pepper white spot disease, white gourd leaf spot disease, celery black rot disease, spinach heart rot disease, kenaf leaf mold disease, kenaf spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown orbicular spot disease, kidney bean red spot disease, bitter gourd leukoderma, watermelon spot disease, jute bottom rot disease, sunflower root stem rot disease, kidney bean carbon rot disease, soybean target spot disease, eggplant rod spore leaf spot disease, cucumber target spot disease, tomato leaf mold, eggplant leaf mold, broad bean red spot disease and the like); basidiomycete diseases such as rust (wheat stripe rust, wheat stalk rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum stalk smut, chestnut kernel smut, sugarcane head smut, kidney bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); ascomycetous diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, towel gourd powdery mildew, pumpkin powdery mildew, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclerotinia rot, rape sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, kidney bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, bitter gourd sclerotinia rot, wax gourd sclerotinia rot, watermelon sclerotinia rot, celery sclerotinia rot), scab (apple scab, pear scab) and the like. Particularly, the composition has good control effect on corn rust, rice blast, tomato black spot and cucumber downy mildew under lower dosage.
Detailed Description
In order to facilitate a further understanding of the invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the present invention and are not intended to limit the scope or the principle of the present invention, and the embodiments of the present invention are not limited to the following.
Example 1
(1) Endophytic fungus of Salix lacrymaPenicilliumsp. (TA33-1) strain culture
The culture medium for culturing the strain contains glucose 1.0 wt%, yeast extract 0.2 wt%, peptone 0.2 wt%, agar 1.0 wt%, sodium chloride 3.0 wt%, and water in balance, and is prepared into test tube slant for culturing fungus strain at 30 deg.C for 3 days.
(2) Endophytic fungus of Salix lacrymaPenicilliumsp. (TA33-1) fermentation
The culture medium used for fermentation culture contains rice 40.0% (by weight, the same below), sodium chloride 3.0%, and water in balance; the fungal strains were cultured at 28 ℃ for 90 days.
(3) Isolation of the Compound of formula I
Taking 60 bottles of mycelium obtained in the step (2), leaching for 3 times by using chloroform-methanol mixed solution (1:1), concentrating under reduced pressure, and extracting for 3 times by using ethyl acetate to obtain a crude extract; performing normal phase silica gel column chromatography (stationary phase is 200-mesh silica gel of 300 meshes; mobile phase is 100% ethyl acetate solvent) and Sephadex LH-20 gel column chromatography (mixed solvent of chloroform and methanol = 1:1, volume ratio), and separating by HPLC high performance liquid preparative chromatography (chromatographic column is Kromasil 10 × 250 mm, 5%μm, the flow rate is 2.0 mL/min, the mobile phase is a 35% methanol-water mixed solvent, and the volume ratio), and concentrating the obtained eluent to obtain yellow powder, namely the compound of the formula I.
Structural validation data for compounds of formula I:
Figure 69882DEST_PATH_IMAGE001
compound of formula I, yellow amorphous powder;1H NMR (600 MHz, CDCl3) δ H7.94 (1H, s, H-1), 7.07 (1H, d, J = 15.6 Hz, H-10),6.65 (1H, s, H-4), 6.09 (1H, d, J = 15.6 Hz, H-9), 5.71 (1H, d, J = 9.6 Hz, H-12), 2.49 (1H, m, H-13), 2.17(3H, s, H-20), 1.85 (3H, s, H-17), 1.57 (3H, s, H-18), 1.44 (1H, m, H-14), 1.34 (1H, m, H-14), 1.02 (3H, d, J=6.6 Hz, H-16), 0.87 (3H, t, J = 7.2 Hz, H-15); 13C NMR (150MHz, CDCl3) δ C191.9 (C6), 186.0 (C8), 170.2 (COCH3), 158.2 (C3), 152.7 (C1), 148.9 (C12), 143.0 (C10), 138.8 (C4a), 132.1 (C11), 115.8 (C9), 114.7 (C5), 110.9 (C8a), 106.4 (C4), 84.7 (C7), 35.2 (C13), 30.2 (C14), 22.6 (C18), 20.3 (C16), 20.1 (COCH3), 12.5 (C17), 12.0 (C15); ESIMS m/z 390.95/392.96 [M + H]+/[M + H + 2]+ (3:1); HRESIMS m/z 391.1314 [M + H]+。
example 2
The bactericidal activity of the compounds of formula I of the present invention was tested according to the following reference test methods: thiyagarajan, V., Harder, T., Qiu, J, W., Qian, P, Y.Mar Biol (Berl) 2003, 143, 543–554. Liu, Q. A.; Shao, C. L.; Gu, Y., C.; Blum, M.; Gan, L. S.; Wang, K. L.; Chen, M.; Wang, C. Y. J. Agric. Food Chem. 2014, 62, 3183–3191。
The test result shows that the compound of the formula I has the effect of treating the melon anthracnose at the concentration of 20 ppmGlomerella lagenariumSeptoria tritici (Sphaerotheca tritici)Septoria triticiShell of gaeumannomyces graminisGaeumannomyces graminisWheat snow mold leaf blightMonographella nivalisFungus coccobacillus arachidicola (L.) KuntzeMycosphaerella arachidis And sclerotinia sclerotiorumSclerotinia sclerotiorum The bacteriostasis rates of the compounds of the formula I are respectively 100%, 50% and 50%, and when the concentration is 200 ppm, the compound of the formula I of the invention has downy mildew resistancePlasmopara viticolaThe bacteriostasis rate of the composite is 50 percent.
Example 4 treatment of infected Sclerotinia sclerotiorum with the Compound of formula I of the present inventionSclerotinia sclerotiorumWheat snow mold leaf blightMonographella nivalisShell of gaeumannomyces graminisGaeumannomyces graminisSeptoria tritici (Miq.) KuntzeSeptoria triticiAnthracnose of melonGlomerella lagenariumMycosphaerella arachidicola (berk.) kuhnMycosphaerella arachidisAnd downy mildewPlasmopara viticolaThe application of crops in prevention and control is not limited to the crops such as wheat, melons, peanuts and the like.
The invention provides an agricultural bactericide, which is characterized in that the bactericide uses the penicillin or salt thereof in the formula I as an effective component for preventing and treating sclerotinia sclerotiorumSclerotinia sclerotiorumWheat snow mold leaf blightMonographella nivalisShell of gaeumannomyces graminisGaeumannomyces graminisSeptoria tritici (Miq.) KuntzeSeptoria triticiAnthracnose of melonGlomerella lagenariumMycosphaerella arachidicola (berk.) kuhnMycosphaerella arachidisAnd downy mildewPlasmopara viticolaCaused agricultural diseases, and endophytic fungi of coral flowersPenicilliumsp. (TA33-1) can be used for large-scale fermentation production, ensures the natural source of the compound of the formula I and has wide application prospect.

Claims (1)

1. An application of the ribicin with the structure of formula I in preventing and treating the agricultural pathogenic bacteria is characterized in that the pathogenic bacteria are sclerotinia sclerotiorumSclerotinia sclerotiorumWheat snow mould leaf blight germMonographella nivalisShell of gaeumannomyces graminisGaeumannomyces graminisSeptoria tritici (Miq.) KuntzeSeptoria triticiColletotrichum gloeosporioidesGlomerella lagenariumMycosphaerella arachidicola (berk.) kuhnMycosphaerella arachidisAnd downy mildewPlasmopara viticolaThe structure of formula I is:
Figure 796536DEST_PATH_IMAGE001
。
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WO2021000062A1 (en) * 2019-06-29 2021-01-07 中山大学 Use of combination of compound of sclerotiorin and rifampicin in preparation of anti-tuberculosis drug
CN110724643B (en) * 2019-11-18 2022-07-15 河南省农业科学院植物保护研究所 Penicillium citrinum with disease prevention and growth promotion functions, microbial inoculum and application thereof

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