CN112189666A - Application of eumycetin alcohol compound in preparation of marine fouling organism control agent - Google Patents

Application of eumycetin alcohol compound in preparation of marine fouling organism control agent Download PDF

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CN112189666A
CN112189666A CN202010982047.8A CN202010982047A CN112189666A CN 112189666 A CN112189666 A CN 112189666A CN 202010982047 A CN202010982047 A CN 202010982047A CN 112189666 A CN112189666 A CN 112189666A
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control agent
marine
compound
organism
larvae
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CN112189666B (en
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严涛
曹文浩
佘志刚
黄锡山
林明晴
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South China Sea Institute of Oceanology of CAS
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/16—Antifouling paints; Underwater paints
    • C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
    • C09D5/1612—Non-macromolecular compounds
    • C09D5/1625—Non-macromolecular compounds organic

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Abstract

The invention discloses an application of a metconazole compound in preparing a marine fouling organism control agent, wherein the structural formula of the metconazole compound is shown as a formula (I). The metrafenol compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at a low dose, so that the metrafenol compound can be used for preparing a marine fouling organism control agent. And the marine organism biological inhibitor is a naturally-occurring organic compound, does not pollute the water environment and cause the enrichment of the marine organism in organisms through food chain transfer, is environment-friendly and high in safety, and effectively inhibits the attachment of marine organismsMeanwhile, the marine biofouling prevention and treatment agent does not contain copper, tin and other heavy metal elements, has good social benefits from the aspect of environmental protection, has large popularization and application potentials, and has good application prospects in marine biofouling prevention and removal.

Description

Application of eumycetin alcohol compound in preparation of marine fouling organism control agent
Technical Field
The invention belongs to the technical field of natural products, and particularly relates to an application of a metrafenone compound in preparation of a marine fouling organism control agent.
Background
The marine fouling organisms refer to various organisms fixed or inhabiting underwater parts of ships and marine facilities, and the harm caused by the marine fouling organisms is mainly to increase resistance, reduce navigational speed, increase fuel consumption and CO2Discharging; blocking a seawater pipeline system, changing a metal corrosion process, and initiating local corrosion or perforation corrosion; the dynamic load effect is increased, so that the drift, unbalance and even overturn of the facility are caused; compete with the cultured objects (such as shellfish) for the attachment base and the bait, hinder the growth and development of the cultured objects and reduce the quality of the products.
The antifouling paint is one of the most widely applied technical methods in preventing and removing marine fouling organisms. However, the traditional antifouling paint takes poison release as a main way, inhibits the attachment of fouling organisms through poisoning action, has the defects of high toxicity, short effective period and the like, and the released antifouling agent also has the risk of harming the marine ecological environment, so that the development of a novel, efficient, low-toxicity and environment-friendly antifouling agent becomes a problem and a research hotspot which are urgently needed to be solved at present.
Since marine fouling organisms are composed of animals, plants and microorganisms, the more harmful and difficult to remove species are mainly limy hulls, sessile stemless vines (barnacles) and bivalve mollusks (mussels and oysters). Therefore, screening tests for antifouling compounds have mostly been performed on stemless vines and bivalves.
In tropical coastal waters, balanus reticulatus is a typical representative of sessile tendrils and is an absolutely dominant species in the biofouling organism community; perna viridis is a common bivalve mollusk in the east and south seas, and is also an important fouling organism species attached to ships, navigations (buoys) and aquaculture facilities. Therefore, the verification test of the invention adopts the balanus reticulates and the perna viridis as experimental objects, and the obtained research results have wide representativeness.
Fouling organisms are generally divided into two life stages, namely a planktonic life stage from the development of larva out of an egg membrane to the intermittent exploration of the surface of an object to prepare for attachment and metamorphosis; once the larvae are selected to be in the settlement position, the larvae are attached to the surface of the attachment base and transformed into larvae, and then the larvae are in the fixation or attachment life stage. From an insult point of view, it begins after fixation or attachment to humans. If the settlement and metamorphosis of the larvae can be effectively inhibited, the purpose of preventing and removing can be achieved. Therefore, the invention adopts the larvae of the two types of marine organisms as experimental objects to test the antifouling effect of the compound, and has scientific reasonability and representative significance.
The clarification of the natural chemical antifouling mechanism of marine organisms can provide reference for developing pollution-free antifouling technology, and the marine organisms themselves are important sources of novel antifouling agents. The content of relevant substances in marine organisms is low, and the structure is relatively complex, so that the marine organism is inconvenient to deeply develop and widely apply. Therefore, the natural antifouling agent is searched from terrestrial plants which have large resource quantity and are convenient for planting and cultivation, and the natural antifouling agent is not only a brand new attempt, but also has important theoretical and practical significance.
A myclobutanol compound, the Chinese name: 3' - (3-hydroxyphenyl) -4-methylspirocyclo [ benzo [ e ]][1,4]Dinitrogen-3, 2' -oxirane]-2,5(1h,4h) -dione, english name: 3' - (3-hydroxypentyl) -4-methylspiro [ e][1,4]diazepine-3,2'-oxirane]-2,5(1H,4H) -dione, white powder, isolated from the mangrove plant kandelia candel endophytic fungus Penicillium spinosum. The molecular formula is C17H14N2O4The molecular weight is 310, and the chemical structural formula is shown as a formula (I).
Figure BDA0002687882500000021
Journal articles have published reports of this compound (Mocamel LW, El-Yamany MF.2012.design and synthesis of novel 1,4-benzodiazepine derivatives and the biological evaluation as Choline enzyme inhibitors. archives of pharmaceutical Research,35(8): 1369-. However, in the field of control of marine fouling organisms, there is no report on the effect of preventing the adhesion of marine fouling organisms and the use thereof in the field of control of fouling organisms.
Disclosure of Invention
The invention aims to provide an application of a metrafenone compound in preparing a marine fouling organism control agent. The structural formula of the eumycetin alcohol compound is shown as the formula (I):
Figure BDA0002687882500000031
the coating amount of the Scirpus validus compound of the present invention is 10 μ g/cm2When the composition is used, obvious inhibition effect is generated on the attachment of barnacle larvae, and the difference is obvious compared with a control group (P)<0.05). The preferred coating amount is 10. mu.g/cm2. Moreover, experiments show that the eumeconol compound has no obvious toxicity to barnacle larvae under the action dosage. The coating amount of the Scirpus validus compound is 1.0 mu g/cm2In time, the attachment rate of mussel larvae was much lower than that of the control group, and the difference was very significant (P)<0.01), indicating that the mycolic alcohol compound can effectively inhibit the attachment of perna viridis larvae. Therefore, the mycolic alcohol compound has good inhibition effect on the adhesion of the tendrils and the bivalves.
Therefore, the first object of the present invention is to provide the use of a metrafenol compound in the preparation of a marine biofouling organism control agent.
Preferably, the marine biofouling organism control agent is a cranberry or bivalve control agent.
Preferably, the cranberry control agent is a barnacle larva control agent, and the bivalves control agent is a mussel larva control agent.
Preferably, the barnacle larva control agent is a balanus reticulatus avenae jinxing larva control agent, and the mussel larva control agent is a perna viridis faceplates larva control agent.
It is a second object of the present invention to provide a marine biofouling organism control agent containing a mycolic alcohol compound as an active ingredient.
Compared with the prior art, the invention has the following beneficial effects:
the metrafenol compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at a low dose, so that the metrafenol compound can be used for preparing a marine fouling organism control agent. The arc fungus alcohol compound is a naturally-existing organic compound, does not pollute the water environment and cause the enrichment of the arc fungus alcohol compound in organisms through food chain transfer, is environment-friendly and high in safety, does not contain heavy metal elements such as copper and tin while effectively inhibiting the attachment of marine organisms, has good social benefits from the aspect of environmental protection, has large popularization and application potential, and has good application prospect in the prevention and removal of marine fouling organisms.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1
Experimental groups: a quantitative amount of the metrafenone compound was dissolved in methanol to a concentration of 282.6. mu.g/mL, and 1mL of the solution was added to a 6 cm-diameter dish so as to uniformly cover the bottom of the dish. After the solvent is completely volatilized, the content of the eubacterium alcohol compound coated on the bottom of the culture dish is 10 mu g/cm2. 13mL of filtered sterile seawater was added.
Control group: adding 1mL of solvent methanol to uniformly distribute the solvent methanol at the bottom of the culture dish, and adding 13mL of filtered and sterilized seawater when the solvent is completely volatilized.
Blank group: 13mL of filtered sterile seawater was added.
Each of the experimental, blank and control groups was provided with 4 replicates. In the adhesion test process, cyprids of balanus reticulatus are randomly distributed to a blank group, a control group and an experimental group, about 30 cyprids are placed in each parallel sample, and the parallel sample is placed in a constant-temperature incubator at the temperature of 30 ℃ to be cultured in a dark environment. After 96 hours of culture, the number of attached larvae in each parallel sample is recorded, the attachment rate of the larvae in each parallel sample (the number of attached larvae/the number of the inserted larvae) is calculated, the average attachment rate of the larvae in each group (namely a blank group, a control group and an experimental group) is counted, the average attachment rate [ (the attachment rate of the parallel sample 1 + the attachment rate of the parallel sample 2 + the attachment rate of the parallel sample 3 + the attachment rate of the parallel sample 4)/4 ] is calculated, the significance test of the difference between groups is carried out, and the effect of the eudipliol compound for inhibiting the attachment of the cyprids of the balanus reticulatus barnacii is confirmed, and the result is shown in table 1.
Table 1 lists the attachment and mortality rates of cyprids of balanus reticulates in the experimental, control and blank groups. As can be seen from table 1, after 96 hours of incubation in the incubator, the attachment ratio of larvae in the blank group was 84.3%, the attachment ratio of larvae in the control group was 84.5%, and there was no significant difference in the attachment ratio of cyprids in the blank group and the control group (P >0.05), indicating that methanol as a solvent was volatilized without leaving harmful substances affecting the activity of cyprids, and thus it was suitable for dissolving the compound. As for the experimental group treated by the Scirpus validus alcohol compound, the attachment rate of the cyprids is 68.3 percent, which is smaller than that of the control group, and the difference is obvious (P is less than 0.05); in addition, the larval mortality rates of the blank group, the control group and the experimental group are all 0, which indicates that the compound can effectively inhibit the attachment of cyprids of balanus reticulatus and the dosage does not have toxic effect on the larvas.
Table 1: attachment status of cyprids of balanus reticulates
Group of Test dose Adhesion Rate (%) Mortality (%)
Blank group － 84.3 0
Control group － 84.5 0
Experimental group 10μg/cm2 68.3 0
Example 2
Experimental groups: the mycolic alcohol compound was dissolved in methanol to prepare a solution having a concentration of 28.26. mu.g/mL. 1mL of this solution was added to a 6cm diameter dish and allowed to cover the bottom of the dish uniformly. After the solvent is completely volatilized, the content of the eubacterium alcohol compound coated at the bottom of the culture dish is 1.0 mu g/cm2. 13mL of filtered sterile seawater was added.
Control group: adding 1mL of solvent methanol to uniformly distribute the solution at the bottom of the culture dish, and adding 13mL of filtered and sterilized seawater when the solvent is completely volatilized.
Blank group: 13mL of filtered sterile seawater was added.
Determination of the number of larvae: taking water containing perna viridis facial disc larvae from the nursery pond and concentrating by bolting silk. Taking 50mL of the water body after three times, dripping 1-2 drops of formalin solution to kill the larvae, and counting under a microscope to obtain an average value, namely the density of the larvae in the water body.
Experiment group, blank group and control group all establish 4 parallel appearance, absorb a certain amount of water that contains emerald mussel faceplates larva according to the density of larva in above-mentioned water for add about 30 larvae in each sample. Culturing in dark environment in an incubator at a temperature of about 26 ℃. After 96 hours of culture, the final attachment condition of each group of larvae is statistically analyzed, the attachment rate of the larvae (the number of attached larvae/the number of inserted larvae) in each parallel sample is calculated, the average attachment rate of the larvae in each group (namely a blank group, a control group and an experimental group) is statistically calculated, the average attachment rate [ (the attachment rate of the parallel sample 1 + the attachment rate of the parallel sample 2 + the attachment rate of the parallel sample 3 + the attachment rate of the parallel sample 4)/4 ] is calculated, and the results of the group difference significance test are shown in table 2.
Table 2 lists the attachment and mortality rates of the young perna viridis faceplates larvae in the experimental, control and blank groups. As can be seen from table 2, after 96 hours of incubation in the incubator, the attachment rate of larvae was about 46.1% for the blank group, about 44.0% for the control group, and no significant difference (P >0.05) was observed between the attachment rates of the larvae of the faceplates of the blank group and the control group, indicating that methanol as a solvent was not left with harmful substances affecting the activity of the larvae of the faceplates after volatilization, and thus it was suitable for dissolving the compound. The attachment rate of larvae of the experimental group treated by the vibriosol compound is only 10.4 percent, which is far lower than that of the control group, and the difference is extremely obvious (P <0.01), which shows that the compound can effectively inhibit the attachment of the larvae of the perna viridis.
Table 2: emerald mussel face plate larva attachment condition
Group of Test dose Percentage of adhesion% The mortality rate is%
Blank group － 46.1 0
Control group － 44.0 0
Experimental group 1.0μg/cm2 10.4 0
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.

Claims (8)

1. The application of the metconazole compound in preparing the marine fouling organism control agent is disclosed, wherein the structural formula of the metconazole compound is shown as the formula (I):
Figure FDA0002687882490000011
2. use according to claim 1, wherein the marine biofouling organism control agent is a cranberry or bivalve control agent.
3. The use according to claim 2, wherein the rumex japonicus-like control agent is a barnacle larva control agent and the bivalves control agent is a mussel larva control agent.
4. The use according to claim 3, wherein said barnacle larvae control agent is balanus reticulatus venus larvae control agent and said mussel larvae control agent is perna viridis epidermophyte control agent.
5. A marine fouling organism control agent is characterized by comprising a metconazole compound as an active ingredient, wherein the metconazole compound has a structural formula shown in formula (I):
Figure FDA0002687882490000012
6. the agent for controlling marine biofouling organisms according to claim 5, wherein the agent for controlling marine biofouling organisms is a cranberry or bivalve control agent.
7. A marine biofouling organism control agent according to claim 6, wherein said fouling organism control agent is a barnacle larva control agent and said bivalves control agent is a mussel larva control agent.
8. The marine biofouling organism control agent according to claim 7, wherein said barnacle larva control agent is a balanus reticulatus venus larva control agent, and said mussel larva control agent is perna viridis epidermoid larva control agent.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106497797A (en) * 2016-11-01 2017-03-15 深圳大学 A kind of extract of fungal cultures and its preparation method and application

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106497797A (en) * 2016-11-01 2017-03-15 深圳大学 A kind of extract of fungal cultures and its preparation method and application

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CUTLER, HORACE G. ET,AL.: "The Biological Properties of Cyclopenin and Cyclopenol", 《PLANT AND CELL PHYSIOLOGY》 *
JUNFENG WANG ET,AL.: "Antifungal New Oxepine-Containing Alkaloids and Xanthones from the Deep-Sea-Derived Fungus Aspergillus versicolor SCSIO 05879", 《J. AGRIC. FOOD CHEM.》 *
MIYAKO KUSANO ET,AL.: "Nematicidal Alkaloids and Related Compounds Produced by the Fungus Penicillium cf. simplicissimum", 《BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY》 *

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