CN111937878B - Application of 2, 3-diaryl chromone compound in preparing marine fouling organism control agent - Google Patents
Application of 2, 3-diaryl chromone compound in preparing marine fouling organism control agent Download PDFInfo
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- CN111937878B CN111937878B CN202010791175.4A CN202010791175A CN111937878B CN 111937878 B CN111937878 B CN 111937878B CN 202010791175 A CN202010791175 A CN 202010791175A CN 111937878 B CN111937878 B CN 111937878B
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- 150000001875 compounds Chemical class 0.000 claims description 17
- 241000237536 Mytilus edulis Species 0.000 claims description 7
- 235000020638 mussel Nutrition 0.000 claims description 7
- 241000238585 Thoracica Species 0.000 claims description 5
- 241000238586 Cirripedia Species 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 241001646398 Pseudomonas chlororaphis Species 0.000 claims 2
- YMHOBZXQZVXHBM-UHFFFAOYSA-N 2,5-dimethoxy-4-bromophenethylamine Chemical compound COC1=CC(CCN)=C(OC)C=C1Br YMHOBZXQZVXHBM-UHFFFAOYSA-N 0.000 claims 1
- 241001072261 Musculista senhousia Species 0.000 claims 1
- 241000545067 Venus Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 230000002401 inhibitory effect Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 230000010071 organism adhesion Effects 0.000 abstract description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052802 copper Inorganic materials 0.000 abstract description 2
- 239000010949 copper Substances 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 241001245601 Perna viridis Species 0.000 description 7
- 239000013535 sea water Substances 0.000 description 7
- 230000003373 anti-fouling effect Effects 0.000 description 6
- 239000002519 antifouling agent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone powder Natural products C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- 241000351392 Amphibalanus reticulatus Species 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 241000238588 Balanus Species 0.000 description 2
- 241000579895 Chlorostilbon Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000237852 Mollusca Species 0.000 description 2
- 240000002044 Rhizophora apiculata Species 0.000 description 2
- 229910052876 emerald Inorganic materials 0.000 description 2
- 239000010976 emerald Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000029052 metamorphosis Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- -1 2- (3- (2,6-dihydroxy-4-methylphenyl) -4-hydroxy-6-methoxy-1-oxo-1H-inden-2-yl) -6-hydroxy-4-methoxyphenoxy Chemical group 0.000 description 1
- GNUJZPJILJOQSW-UHFFFAOYSA-N 2-[2-[3-(2,6-dihydroxy-4-methylphenyl)-4-hydroxy-6-methoxy-1-oxoinden-2-yl]-6-hydroxy-4-methoxyphenoxy]-6-hydroxy-4-methylbenzoic acid Chemical compound OC1=C(C(=CC(=C1)C)O)C1=C(C(C2=CC(=CC(=C12)O)OC)=O)C1=C(OC2=C(C(=O)O)C(=CC(=C2)C)O)C(=CC(=C1)OC)O GNUJZPJILJOQSW-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100410811 Mus musculus Pxt1 gene Proteins 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000003653 coastal water Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 125000000830 polyketide group Chemical group 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
Classifications
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- 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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- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an application of a 2, 3-diaryl chromone compound in preparing a marine fouling organism control agent, wherein the structural formula of the 2, 3-diaryl chromone compound is shown as a formula (I). The 2, 3-diaryl chromone compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at a low dose, and therefore, can be used for preparing a marine fouling organism control agent. The marine biofouling inhibitor is a naturally-occurring organic compound, does not pollute the water environment and cause the enrichment of the marine biofouling inhibitor 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 potentials, and has good application prospects in the prevention and removal of marine biofouling organisms.
Description
Technical Field
The invention belongs to the field of natural products, and particularly relates to an application of a 2, 3-diaryl chromone 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.
The name of the 2, 3-diaryl Yitong compound is 2- (2- (3- (2,6-dihydroxy-4-methylphenyl) -4-hydroxy-6-methoxy-1-oxo-1H-indene-2-yl) -6-hydroxy-4-methoxyphenoxy) -6-hydroxy-4-methylbenzoic acid, the English name is 2- (2- (3- (2,6-dihydroxy-4-methylphenyl) -4-hydroxy-6-methoxy-1-oxo-1H-inden-2-yl) -6-hydroxy-4-methoxyphenoxy) -6-hydroxy-4-methyibenzoic acid, a reddish brown crystal derived from a mangrove endophytic fungusAscomycota sp.SK2YWS ' ' ' L. The molecular formula is C32H26O11The molecular weight is 586, and the chemical structural formula is shown as formula (I).
The structure of the 2, 3-diarylchromone compound has been reported (Tan C, Liu Z, Chen S, et al, 2016. Anisotropic polyketides from the Mangrove-depleted fungi)Ascomycotasp. SK2YWS-L. Scientific Reports, 6: 36609.), but in the field of marine biofouling organism control, there is no report on the disclosure of the anti-marine biofouling organism adhesion and its use in the field of biofouling organism control.
Formula (I).
Disclosure of Invention
The invention aims to provide application of a 2, 3-diaryl chromone compound in preparing a marine fouling organism control agent.
The 2, 3-diaryl xanthone compound of the present invention was coated in an amount of 10. mu.g/cm2When the composition is used, obvious inhibition effect on the attachment of barnacle larvae is produced (p<0.05). The preferred coating amount is 10. mu.g/cm2. Moreover, experiments show that, under the action dosage,the 2, 3-diaryl chromone compound has no obvious toxicity to barnacle larvae. The 2, 3-diaryl xanthone compound was applied in an amount of 1.0. mu.g/cm2In time, the attachment rate of mussel larvae is far lower than that of a control group, and the difference is significant (p<0.05), indicating that the 2, 3-diarylchromone compound is effective in inhibiting the attachment of perna viridis larvae. It can be seen that the 2, 3-diaryl chromone compounds have good inhibitory effects on the adhesion of tendrils and bivalves.
Therefore, the invention provides the application of a 2, 3-diaryl chromone compound in preparing a marine fouling organism control agent, wherein the structural formula of the 2, 3-diaryl chromone compound is shown as the formula (I):
formula (I).
The marine biofouling organism control agent is preferably a barnacle larva control agent (such as a balanus reticulatus larva control agent) or a mussel larva control agent (such as a perna viridis epidermoid larva control agent).
Compared with the prior art, the invention has the following beneficial effects:
the 2, 3-diaryl chromone compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at a low dose, and therefore, can be used for preparing a marine fouling organism control agent. The 2, 3-diaryl ketone printing compound is a naturally-existing organic compound, does not pollute the water environment and cause the enrichment of the compound in organisms through food chain transmission, 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.
The specific implementation mode is as follows:
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 2, 3-diarylxanthone compound was dissolved with methanol so that the concentration of the 2, 3-diarylxanthone compound was 282.6. mu.g/mL, and 1 mL of the solution was added to a 6 cm-diameter petri dish and allowed to uniformly cover the bottom of the petri dish. After the solvent was completely volatilized, the content of the 2, 3-diarylchromone compound coated on the bottom of the petri dish was 10. mu.g/cm2. 13 ml of filtered sterile seawater was added.
Control group: adding 1 ml of methanol to uniformly distribute the methanol at the bottom of the culture dish, and adding 13 ml of filtered and sterilized seawater when the methanol is completely volatilized.
Blank group: 13 ml of filtered sterile seawater was added.
Each of the experimental, blank and control groups was provided with 4 replicates. In the adhesion test process, barnacle larvae are randomly distributed to a blank group, a control group and an experimental group, about 30 larvae are placed in each parallel sample, and the sample is placed in a constant-temperature incubator at the temperature of 30 ℃ to be cultured in a dark environment. After 120 hours of culture, the number of attached larvae in each parallel sample was recorded, the attachment rate of larvae (number of attached larvae/number of inserted larvae) in each parallel sample was calculated, the average attachment rate of larvae in each group (i.e., blank group, control group, and experimental group) [ (attachment rate of parallel sample 1 + attachment rate of parallel sample 2 + attachment rate of parallel sample 3 + attachment rate of parallel sample 4)/4 ] was counted, and the significance of differences between groups was examined to confirm the effect of the related compound in inhibiting the attachment of pot larvae. The adhesion rate calculation method of example 2 was also calculated with reference to this method.
Table 1 lists the attachment and mortality rates of the cyprids of the experimental, control and blank groups. As can be seen, after 120 hours of culture in the constant temperature incubator, the attachment rate of the larvae of the blank group is 34.7%, the attachment rate of the larvae of the control group is 35.4%, and the attachment rates of the cyprids of the blank group and the cyprids of the control group have no significant difference (the attachment rates of the cyprids of the blank group and the cyprids of the control group are not significantly different: (the attachment rates of the cyprids of the control group are not significantly different) (the stepp>0.05), indicating that methanol as solvent does not leave harmful substances affecting the activity of the cyprids after volatilization, and is suitable for dissolving the compound. For the experimental group treated with 2, 3-diaryl xanthone compound, the attachment rate of cyprids was 20.4%, which was smaller than that of the control group, and the difference was significant (p<0.05); in addition, the mortality rates of larvae in the blank group, the control group and the experimental group were all 0It is shown that this compound is effective in inhibiting the attachment of cyprids larvae of balanus reticulatus and that this dose does not have a poisoning effect on the larvae.
Table 1: attachment status of cyprids of balanus reticulates
Example 2
Experimental groups: the 2, 3-diaryl xanthone compound was dissolved in methanol as a solvent to prepare a solution having a concentration of 28.26. mu.g/mL. 1 mL of this solution was added to a 6cm diameter dish and allowed to cover the bottom of the dish uniformly. After the solvent was completely volatilized, the content of the 2, 3-diarylchromone compound coated on the bottom of the petri dish was 1.0. mu.g/cm2. 13 mL of filtered sterile seawater was added.
Control group: adding 1 mL of methanol to uniformly distribute the solution at the bottom of the culture dish, and adding 13 mL of filtered and sterilized seawater when the solvent is completely volatilized.
Blank group: 13 mL 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 50 mL 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 ℃. Statistical analysis of the final attachment and death status of each group of larvae was performed after 72 hours of culture.
Table 2 lists the attachment and mortality rates of perna viridis larvae in the experimental, control and blank groups. As can be seen, after 72 hours of incubation in the incubator, the attachment rate of larvae in the blank group was about 44.5%, that in the control group was about 46.2%, and there was no significant difference in the attachment rate of larvae in the face plates between the blank group and the control group ((ii)p>0.05), indicating as solventThe methanol can not leave harmful substances which affect the activity of the faceplates larvae after volatilization, and is suitable for dissolving the compound. The experimental group treated by the 2, 3-diaryl chromone compound has the larva attachment rate of only 16.7 percent, which is far lower than that of the control group, and the difference is significant (p<0.05), indicating that the compound is effective in inhibiting the attachment of perna viridis larvae. Table 2: emerald mussel face plate larva attachment condition
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