CN105669524A - Compound for controlling dragon fruit anthracnose and composition using compound - Google Patents

Compound for controlling dragon fruit anthracnose and composition using compound Download PDF

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Publication number
CN105669524A
CN105669524A CN201610128193.8A CN201610128193A CN105669524A CN 105669524 A CN105669524 A CN 105669524A CN 201610128193 A CN201610128193 A CN 201610128193A CN 105669524 A CN105669524 A CN 105669524A
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CN
China
Prior art keywords
compound
organic compound
anthrax
hylocereus undatus
composition
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CN201610128193.8A
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Chinese (zh)
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CN105669524B (en
Inventor
罗会
裴晓红
马玉华
蔡永强
张兴无
李金强
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Guizhou Alpine Agricultural Technology Service Co ltd
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GUIZHOU FRUIT INSTITUTE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Abstract

The invention provides an organic compound for controlling dragon fruit anthracnose and a composition using the organic compound. The organic compound can be prepared into soluble solutions, microemulsions, aqueous emulsions, suspoemulsions, seed coatings, wettable dust granules, slow-release granules, controlled-release granules, water-dispersible granules, dry suspoemulsions, directly used granules or other preparation formulations. The composition is used for controlling dragon fruit anthracnose.

Description

A kind of compound preventing and treating Hylocereus undatus anthrax and apply its compositions
Technical field
The present invention relates to agricultural chemical compound and compositions field thereof, particularly to a kind of compound preventing and treating Hylocereus undatus anthrax and compositions thereof.
Background technology
Agricultural is the basis of Chinese national economy, but plant disease brings incalculable damage to China or even whole world agricultural production, therefore, it is carried out one of effective prevention and control essential measure being to ensure that agricultural high-effiency production and stable development, current main means of prevention is extensively using of pesticide. and therefore, agriculture for China or even national economy the development of research and development with China's independent intellectual property right pesticide has particularly important strategic importance. and the research and development of the antibacterial agent of novel structure are always up the difficult problem that people capture.
It is documented, nearly 100,000 kinds of the fungus of nature, wherein harmful pathogenic fungi reaches kind more than 8000, and fungus-caused disease accounts for the 80% of plant disease total amount, very harmful. the fungus having also can make the moldy metamorphisms such as agricultural product, timber, food, and even parasitizing of having causes dermatosis in people and animals' body. In addition fungus breeding speed is fast; transmission capacity is strong; it is difficult to be removed; thus causing very big impact to quality and the yield of crops and agricultural product. how to take the effectively method of environmental protection preventing and treating pathogenic fungi; it is the key of peasant's increasing both production and income and ecological environmental protection. in recent years; China achieves bigger progress in the study on prevention of phytopathogen, but there is also certain problem simultaneously. The straightforward procedures such as traditional cultural control crop rotation are not implemented very well, make these diseases day by day serious, chemical pesticide control is still the Main Means of current control of plant disease, but the large area of chemistry antibacterial frequently uses and causes that it is produced serious Drug resistance by pathogen. therefore, it is necessary development structure novel and the antibacterial of wide spectrum. for this, we devise a kind of compound, and its inhibitory activity to Hylocereus undatus anthrax pathogen of system thinking.
Hylocereus undatus anthrax easily occurs in stem, the scab initial stage is water stain shape fleck, surrounding has yellow dizzy, the Semen phaseoli radiati circular scab to Semen arachidis hypogaeae size is become after expansion. during air dry drought on the same day, scab stops growth, it is transformed into the brown scab that yellowish-brown is slightly swelled, suberification tissue. when wet weather, suberification scab can be expanded into big speckle, the stem meat even making portion is completely rotten, the epidermis rotted produces black the big speckle of wheel stricture of vagina. on fruit, fruit is injured beginning also in water stain shape dirty-green fleck, these stigmas can heal, and it is expansible, but they only harm peel shallow-layer cells making tissue flavescence brown suberification of being injured affect appearance.
But; in view of the method being used at present preventing and treating Hylocereus undatus anthrax disease; still need further exist for the Hylocereus undatus anthrax disease control increased. but; these methods are not exclusively satisfactory at disease control domain variability; therefore exist and require preventing and treating is provided and resists disease and protect plant, in addition it is also necessary to reduce disease and obtain the speed that the tolerance to Disease Resistance raise crop and pesticide increases.Also need to the service life of extension Disease Resistance raise crop and pesticide.
Summary of the invention
Present invention aim at providing a kind of organic compound preventing and treating Hylocereus undatus anthrax and compositions thereof, to be solved technical problem is that prevents and treats Hylocereus undatus anthrax.
The organic compound of described preventing and treating Hylocereus undatus anthrax, it has following chemical structural formula:
Preferably, it is crystal, and described crystal belongs to monoclinic system, and its space group is C2/c, β=95.45 °.
Described organic compound auxiliary agent acceptable with on pesticide, surfactant, solvent prepare into composition pesticide with carrier;
Described auxiliary agent and surfactant are preferably one or more in dispersing agent NNO, sodium lauryl sulphate, dispersing agent MF, sodium lignin sulfonate, agriculture breast 600#, fatty alcohol-polyoxyethylene ether, naphthalene sulfonic acid formaldehyde condensation polymer, ammonium sulfate, emulsifying agent 603#, calcium dodecyl benzene sulfonate 500#; One or more in the preferred isopropanol of described solvent, dimethylformamide, Ketohexamethylene, ethyl acetate, dimethylbenzene; One or more in the preferred white carbon of described carrier, Kaolin, water, potter's clay.
Described compositions can be prepared for soluble liquid, microemulsion, aqueous emulsion, suspension emulsion, seed coat agent, wettable powder granule, sustained-release granular formulation, controlled release granule, water dispersible granules, dry suspension emulsion, or the granule directly used;
Described compositions can prevent and treat Hylocereus undatus anthrax.
Detailed description of the invention
The invention will be further described by the examples below. It should be understood that; preparation method described in the embodiment of the present invention is only used for the present invention is described; rather than limitation of the present invention; under the concept thereof of the present invention, the simple modifications of preparation method of the present invention is broadly fallen into the scope of protection of present invention. all raw materials used in embodiment and solvent; if no special instructions, all purchased from SigmaBiochemicalandOrganicCompoundsforResearchandDiagnos ticClinicalReagents company.
Reagent and the medicament used in embodiment are commercially available prod.
Preparation embodiment 1:
(1) by 1mmol1,3, the fluoro-2-benzene-1 of 4-tri-'-methyl-methanol (purchased from Shanghai Yaoming Kangde New Medicine Development Co., Ltd) joins in single port bottle, add after 100mL dichloromethane is dissolved and add 1.8mmol triethylamine, drip 1.4mmol mesyl chloride under low temperature, dropwise and return to room temperature reaction. Reaction uses 1mol/L salt acid elution 2 times after terminating, and saturated sodium-chloride washs 1 time, and anhydrous sodium sulfate dries, and is spin-dried for and obtains brownish red oily liquids, without being further purified, is directly used in next step reaction.
(2) in single port bottle, 2.5mmol step (1) product and 100mlDMF are added, add 2.4mmol4-isoindoline Ethyl formate after dissolving and add 2mmol cesium carbonate, oil bath heating is 105 DEG C to outer temperature. reaction adds substantial amounts of water after terminating, it is extracted with ethyl acetate again, it is spin-dried for column chromatography for separation and obtains pale yellow oily liquid body, without being further purified, it is directly used in next step reaction.
(3) by 5mmol step (2) product when ethanol and water as solvent, add NaOH (2.2eq) 45 DEG C reaction saponification, it is 6-7 that addition dilute hydrochloric acid is adjusted to PH, drain addition ethanol filtration after concentration to be spin-dried for, column chromatography for separation obtains faint yellow solid, without being further purified, it is directly used in next step reaction.
(4) 10mmol step (3) product and 12mmol aniline are joined 100mL single port bottle adds 10mLDMF stirring molten clearly, add 1mmolHBTU, 0.8mmol triethylamine, reactant liquor is poured into water after terminating by room temperature reaction 5h. reaction, it is extracted with ethyl acetate again, anhydrous sodium sulfate dries and is spin-dried for, and column chromatography for separation obtains white powdery solids compound, yield 48%.
Structural Identification:
1HNMR (DMSO-d6): δ (ppm), 10.20 (s, 1H, NH), 7.96 (s, 1H, CH), 7.89 (d, 1H, CH), 7.70 (m, 2H, 2CH), 7.49 (d, 1H, CH), 7.32 (m, 2H, 2CH), 7.13 (m, 1H, CH), 7.07 (m, 1H, CH), 6.98 (m, 1H, CH), 4.01 (t, 1H, CH), 3.62 (s, 4H, 2CH2), 1.27 (d, 3H, CH3).
Preparation embodiment 2:
The Formulas I organic compound of above-mentioned preparation is placed in quartz ampoule (quartzampoule). at temperature 107～108 DEG C, by this compound vacuum dehydration prepared. this pipe is disengaged, and is placed in crystal growing furnace. By Bridgman (Bridgman) method growth crystal in the dual stove (doublefurnace) have isolating membrane. final, obtain colourless web crystal. this crystal is carried out Advances in crystal X-ray diffraction crystallographic analysis, its crystallographic parameter is as follows: monoclinic system, its space group is C2/c β=95.45 °.
Preparation embodiment 3:
Processing method: above raw material etc. join after weighing by proportioning in shearing tank, shears and within 30 minutes, makes mixing of materials uniform, open recirculated water, by material ball milling with a certain amount of flow, temperature controls less than 40 degree, and fineness crosses 325 mesh sieves, after grinding 1.5h, obtain uniform emulsion liquid.
Preparation embodiment 4:
Each raw material is added mix and blend in double worm mixer, pulverizes then through jet mill, mix by again passing by double worm mixer after 325 mesh sieves and obtain product.
Preparation embodiment 5:
By said mixture Homogeneous phase mixing, comminution by gas stream, add suitable quantity of water and mediate, the mixture pelleting of gained, it is drying to obtain product. the addition of the auxiliary agents such as naphthalene sulfonic acid formaldehyde condensation polymer, sodium lauryl sulphate, ammonium sulfate, potter's clay, both made for dosage form and provided safeguard, the dispersibility that product maintenance is good can be made again, the tack of target surface is relatively good.
BIOLOGICAL ACTIVITY EXAMPLES 1:
The PPAR δ activity of the compound represented by Formulas I of the present invention confirms by transfecting detection. it addition, the selectivity for PPAR hypotype PPAR α and PPAR γ is also carried out inspection. Test cell toxicity is detected, by animal experiment study activity in vivo by MTT.
This detection uses CV-1 cell. Described cell is seeded in 96 orifice plates containing the DMEM being added with 10%FBS, DBS (DBS, through defat) and 1% penicillin/streptomycin, and at 37 DEG C, 5%CO2Incubator in cultivate. experiment according to inoculation, transfection, the step of sample administration and confirmation carries out. specifically, CV-1 cell is seeded to 96 orifice plates (5000 cells/well), transfect after 24 hours. by total length PPAR plasmid DNA, the reporter dna of PPAR activity is can confirm that because having uciferase activity, there is provided the beta galactosidase DNA about transfection efficiency information and transfection reagent for transfecting. dissolve a sample in dimethyl sulfoxide (DMSO), by medium, it is administered in cell with variable concentrations. in incubator, cultivate cell after 24 hours, by using lysis buffer to make lysis. use photometer and microplate reader to measure uciferase activity and betagalactosidase activity. the value of the luciferase using the value correction of beta galactosidase to obtain. utilize these value graphings, and calculate EC50。
Compound hPPARδ hPPARα hPPARγ
I 2.4nM ia ia
The compound of the present invention has high selectivity for PPAR δ as can be seen here.
Perform the cytotoxicity .MTT that MTT detection is the compound represented by formula (I) in order to test the present invention and be dissolved in the yellow substance of water, but can become, by the dehydrogenase in mitochondrion, the crystal that purple is insoluble when it is introduced in living cells. can pass through to measure OD550 after being dissolved in dimethyl sulfoxide by MTT and confirm cytotoxicity. test and be carried out as follows.
CV-1 cell is inoculated in 96 orifice plates (5000 cells/well).At 37 DEG C, 5%CO2Incubator in cultivate described cell 24 hours, and it is used the sample of variable concentrations. then, again described cell is cultivated 24 hours, it is added thereto to MTT reagent. after cultivating 15 minutes, the purple crystals generated is dissolved in dimethyl sulfoxide. and use microplate reader to measure optical density, to confirm cytotoxicity.
As a result, formula (I) compound represented is identified does not have cytotoxicity for PPAR, even if being EC in its concentration50Value 100 times～1000 times time also such.
BIOLOGICAL ACTIVITY EXAMPLES 2: the antibacterial activity of compound of formula I
1. for examination bacterium
Hylocereus undatus anthrax fungal pathogens, colletotrichum gloeosporioides Penz (Colletotrichumgloeosporioides), separated by Guizhou University's fungus resource institute and provided.
2.PDA culture medium is prepared
Total amount according to required culture medium, according in every 1000mL water add 200g Rhizoma Solani tuber osi, 15g agar, 20g glucose amount weigh raw material and prepare culture medium. specifically comprise the following steps that in stainless-steel pan, add appropriate distilled water, heating to boiling; The Rhizoma Solani tuber osi wash clean that will weigh up, peeling, stripping and slicing, add when water seethes with excitement in pot, big fire regulates firing rate after boiling, and keeps micro-30min that boils; With the above-mentioned mixed liquor of the filtered through gauze building up eight layers to volume required, regulate pH to 7, add load weighted agar and glucose in advance, be stirred well to mix homogeneously, be divided in conical flask after accurately weighing aequum with graduated cylinder, seal with special-purpose sealing film, stand-by.
3. test sample solution preparation
Precise testing sample, is loaded in the bottle of 20mL, adds precalculated appropriate dimethyl sulfoxide (DMSO) with liquid-transfering gun, and ultrasonic Treatment makes it be completely dissolved, and covers bottle cap, puts in superclean bench; Then open uviol lamp, irradiate equipped with the bottle treating sample measuring liquid, sterilizing 30min; The amount that volume ratio is 1: 19 according to DMSO Yu sterilized water, add in sample bottle with the sterile distilled water that the pipette, extract of sterilizing in advance is quantitative, testing sample is configured to the confession test liquid of 5%, after it is fully mixed stand-by. making negative control with isopyknic 5%DMSO aqueous solution, positive drug compound method is identical with testing sample.
4. the compound of formula I In Vitro Bacteriostatic to Hylocereus undatus anthrax fungal pathogens
Accurately weigh 5mg compound of formula I with 20mL bottle, inject 0.5mLDMSO and 9.5mL sterilized water wherein, testing sample is made into the DMSO solution of 5%; In the 90mLPDA culture medium melted after being subsequently adding sterilizing, mixing, is made into the 100mL culture medium containing testing sample, pours in sterile petri dish, make with medicine plating medium. using the equivalent solvent i.e. DMSO of 5% as blank, using commercial antimicrobial medicine kresoxim-methyl as positive control.
Colony edge eugonic Hylocereus undatus anthrax pathogen bacterium cake is taken out with the card punch that diameter is 5mm, transferring them on above-mentioned plating medium with Inoculating needle, mycelia one faces down, and is attached in culture medium, 3 pieces of every ware, triangular in shape being positioned over central authorities, add a cover and be placed in constant incubator and cultivate, temperature is 26 DEG C, humidity is 80%, after illumination is set to 0%.72h, adopts decussation method ruler to measure the square crossing diameter of bacterium colony, take its meansigma methods. often process and set 3 repetitions.
It is calculated as follows bacteriostasis rate:
Mycelial growth inhibition rate (%)={ [blank colony diameter processes colony diameter] }/[blank colony diameter-5] × 100
The average inhibition of Hylocereus undatus anthrax fungal pathogens is 79.8 ± 1.1 (%) at 50 μ g/ml by compound of formula I, and the average inhibition of Hylocereus undatus anthrax fungal pathogens is 69.3 ± 0.1 (%) at 50 μ g/ml by kresoxim-methyl.
BIOLOGICAL ACTIVITY EXAMPLES 3: embodiment 3-5 is to Hylocereus undatus anthrax field control effectiveness test in preparation:
11 last ten-days period, Guizhou Bijie Hylocereus undatus invention rule is investigated, utilize preparation embodiment 3-5 as reagent agent, every 10d dispenser 1 time, spray medicine 4 times continuously, and before spray medicine every time, investigate disease index and the poisoning situation of each process. test adopts the group arrangement of random district, often process regularly spray medicine and investigate 3 strains, repeat for 3 times.
Disease scale standard: 0 grade, fleshy stem is without scab; 1 grade, fleshy stem 1～10/10cm of scab number; 2 grades, fleshy stem 11～30/10cm of scab number; 3 grades, fleshy stem 31～50/10cm of scab number; 4 grades, fleshy stem scab number more than 50/10cm. prevention effect is as follows:
In conjunction with field efficacy experimental result, it can thus be seen that Hylocereus undatus anthrax is had higher prevention effect by compound of formula I and compositions thereof.

Claims (5)

1. the organic compound preventing and treating Hylocereus undatus anthrax, it is characterised in that represent with following chemical structural formula:
2. organic compound according to claim 1, it is characterised in that it is crystal, described crystal belongs to monoclinic system, and its space group is C2/c,β=95.45 °.
3. a composition pesticide, it is characterised in that it includes acceptable auxiliary agent, surfactant, solvent and carrier on the arbitrary described organic compound of claim 1-2 and pesticide.
4. the compositions described in claim 3, it can be made into soluble liquid, microemulsion, aqueous emulsion, suspension emulsion, seed coat agent, wettable powder granule, sustained-release granular formulation, controlled release granule, water dispersible granules, dry suspension emulsion or the granule directly used.
5. the purposes in preventing and treating Hylocereus undatus anthrax of the compositions described in claim 3.
CN201610128193.8A 2016-03-07 2016-03-07 It is a kind of prevent dragon fruit anthracnose compound and apply its composition Expired - Fee Related CN105669524B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5326766A (en) * 1992-08-19 1994-07-05 Dreikorn Barry A 4-(2-(4-(2-pyridinyloxy)phenyl)ethoxy)quinazoline and analogues thereof
CN102415394A (en) * 2011-12-06 2012-04-18 海利尔药业集团股份有限公司 Indoxacarb-containing high-efficiency pesticidal composition
CN103125493A (en) * 2011-12-04 2013-06-05 海利尔药业集团股份有限公司 Insecticide composition mixed with amides pesticide
CN104650036A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 6-substituented phenyl quinazolinone compound and use thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5326766A (en) * 1992-08-19 1994-07-05 Dreikorn Barry A 4-(2-(4-(2-pyridinyloxy)phenyl)ethoxy)quinazoline and analogues thereof
CN103125493A (en) * 2011-12-04 2013-06-05 海利尔药业集团股份有限公司 Insecticide composition mixed with amides pesticide
CN102415394A (en) * 2011-12-06 2012-04-18 海利尔药业集团股份有限公司 Indoxacarb-containing high-efficiency pesticidal composition
CN104650036A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 6-substituented phenyl quinazolinone compound and use thereof

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