CN115803310A - Bactericide and method of sterilizing - Google Patents

Bactericide and method of sterilizing Download PDF

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CN115803310A
CN115803310A CN202080102727.4A CN202080102727A CN115803310A CN 115803310 A CN115803310 A CN 115803310A CN 202080102727 A CN202080102727 A CN 202080102727A CN 115803310 A CN115803310 A CN 115803310A
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胡安仁
施增廉
洪崧壬
陈灏平
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TZU CHI UNIVERSITY
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C07C49/233—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C49/235—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic rings
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    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • C07C49/248—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Abstract

The invention provides a bactericide and a sterilization method, wherein the bactericide comprises a compound shown in a chemical formula I:
Figure DDA0004035564740000011
wherein Ar is 1 And Ar 2 Each independently is a phenyl, naphthyl, thienyl, furyl or pyridyl group, unsubstituted or substituted by a substituent, and Ar 1 And Ar 2 The same or different; the substituent is selected from the group consisting of halogen, hydroxyl, alkyl and alkoxy; when Ar is 1 And Ar 2 When each is independently phenyl substituted with two substituents, ar 1 And Ar 2 Different.

Description

Bactericide and method of sterilizing Technical Field
The invention relates to a bactericide and a sterilization method.
Background
Curcumin (curcumin) is a yellow pigment extracted from turmeric (turmeric), and is the most prominent curcumin in turmeric, accounting for about 70% of curcumin. In addition to curcumin, curcuminoids (curcuminids) are one of the components in turmeric plants, and mainly include demethoxycurcumin (about 10-20%), dimethoxycurcumin (about 10%), hexahydrocurcumin, and the like.
Figure PCTCN2020114821-APPB-000001
Curcumin is used in medical and health foods because of its good action on the human body. Many studies have pointed out that curcumin has various clinical medical effects such as anti-inflammation, anti-bacteria, anti-tumor, anti-oxidation, anti-obesity and prevention of chronic diseases, so many curcumin health foods are sold on the market in recent years. In addition, curcumin can also be used as a good photosensitizer, has an absorption wavelength range of 210-510nm, covers the blue light part of ultraviolet light and visible light, and can generate free radicals after being irradiated by specific wavelengths, so that drug-resistant bacteria can lose activity and have an anti-tumor cell effect. In addition, curcumin enhances epithelial regeneration and increases fibroblast growth and vascular density in wounds, increases the rate of wound healing and inhibits melanogenesis in human melanocytes by activating the Akt/GSK3 β, ERK or p38MAPK signaling pathways. The daily allowable intake (ADI) of curcumin is 0-3mg/kg body weight as reported by JECFA (Joint national and world health organization Joint food additives experts Committee) and EFSA (European food safety agency).
Disclosure of Invention
The invention aims to further provide a compound which can improve the sterilizing effect more effectively compared with curcumin and is effectively applied to a bactericide.
The invention provides a bactericide, which comprises a compound shown in a chemical formula I:
Figure PCTCN2020114821-APPB-000002
wherein, the first and the second end of the pipe are connected with each other,
Ar 1 and Ar 2 Each independently is a phenyl, naphthyl, thienyl, furyl or pyridyl group, unsubstituted or substituted by a substituent, and Ar 1 And Ar 2 The same or different;
the substituent is selected from the group consisting of halogen, hydroxyl, alkyl and alkoxy;
when Ar is 1 And Ar 2 When each is independently phenyl substituted with two substituents, ar 1 And Ar 2 Different.
Preferably, the compound of formula I is selected from at least one of the following compounds 1 to 11:
Figure PCTCN2020114821-APPB-000003
Figure PCTCN2020114821-APPB-000004
preferably, the bacterial species that the bactericidal agent is capable of killing and/or inhibiting comprises aerobic bacteria.
Preferably, the bacterial species that the bactericidal agent is capable of killing and/or inhibiting comprises gram positive bacteria.
Preferably, the gram-positive bacteria comprise staphylococcus epidermidis or staphylococcus aureus.
Preferably, the concentration of the compound of formula I is 0.5ppm to 1ppm.
The invention also provides a sterilization method, which comprises the following steps: contacting the compound shown in the chemical formula I with a strain; and applying a wavelength of 410-510nm (lambda) to the compound max =462 nm).
The bactericide and the sterilization method of the invention have at least one of the following advantages:
1. the compounds for sterilization are all artificially synthesized, have high purity, and have better sterilization effect compared with three mixtures in natural curcumin.
2. Although curcumin and its derivatives are known to have bactericidal effects, it is not necessarily effective against any bacterial species. The curcuminoids used in the present invention have a relatively high bactericidal capacity against aerobic bacteria species.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application, are incorporated in and constitute a part of this application, and are not intended to limit the application. In the drawings:
FIG. 1 shows the bactericidal effect of curcumin or curcuminoids on Staphylococcus epidermidis.
FIG. 2 is an SEM image of the effect of compound 8 on Staphylococcus epidermidis structure before and after blue light irradiation, wherein (a) is before irradiation, (b) is after 1 minute of irradiation, and (c) is after 5 minutes of irradiation.
Fig. 3 is a graph showing the results of stability tests of curcuminoids, in which (a) is compound 1, (b) is compound 8, and (c) is compound 9.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention will be described in detail and fully with reference to the accompanying drawings, in which the described embodiments are only a part, but not all, of the present application.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. If a definition used herein conflicts or is inconsistent with a definition set forth in other publications, the definition used herein shall govern.
As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion.
When a value or parameter is given as either a range, preferred range, or a list of upper and lower values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range is recited as "1 to 5," the recited range should be understood to include the ranges "1 to 4," "1 to 3," "1 to 2 and 4 to 5," "1 to 3 and 5," and so forth. If a range of values is recited in this specification, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range.
Furthermore, "or" means an inclusive "or" and not an exclusive "or" unless expressly specified otherwise. For example, the condition a "or" B "satisfies any of the following cases: a is true (or present) and B is false (or not present), a is false (or not present) and B is true (or present), and both a and B are true (or present).
Similarly, the indefinite articles "a", "an" and "an" preceding an element or component herein are intended to describe without limitation the number of instances (i.e., occurrences) of the element or component, unless the context clearly indicates otherwise. Thus, "a", "an" and "the" are to be understood as including one or at least one, and the singular forms of the elements or components also include the plural.
The term "kill" as used herein means having the ability to kill, destroy or destroy a bacterial species, reduce the number of bacterial species, and/or inhibit the proliferation of bacterial species.
In one embodiment, the present invention provides a fungicide comprising a compound represented by formula I:
Figure PCTCN2020114821-APPB-000005
wherein the content of the first and second substances,
Ar 1 and Ar 2 Each independently is a phenyl, naphthyl, thienyl, furyl or pyridyl group, unsubstituted or substituted by a substituent, and Ar 1 And Ar 2 The same or different;
the substituent is selected from the group consisting of halogen, hydroxyl, alkyl and alkoxy;
when Ar is 1 And Ar 2 When each is independently phenyl substituted with two substituents, ar 1 And Ar 2 Different.
Examples
In the examples, 17 kinds of synthesized curcuminoids were used for experimental comparison with Curcumin (Curcumin I) as a comparative example, and the structures thereof are respectively as follows:
Figure PCTCN2020114821-APPB-000006
Figure PCTCN2020114821-APPB-000007
experimental method
Culture of the Strain
Strain 1: taking out Staphylococcus epidermidis (Staphylococcus epidermidis TCU-1 BCRC 81267) from a refrigerator at the temperature of-80 ℃, dipping the Staphylococcus epidermidis in an inoculating loop, dividing three areas on an LB culture medium, placing the inoculating loop in an incubator at the temperature of 37 ℃ for 12 hours, culturing one colony on an inoculating loop taking plate in 10ml of LB culture medium at the temperature of 37 ℃ for 12 hours the next day, and measuring the absorbance OD 600nm =1, wherein the bacterial number concentration is about 10 9 CFU/ml, centrifugation at 2000Xg for 10 min, and removal of supernatant.
And (3) strain 2: from ice at-80 DEG CTaking Staphylococcus aureus (Staphylococcus aureus subsp. Aureus TCU-2 BCRC81268) out of the box, dipping the strain liquid by an inoculating loop, dividing three zones on an LB culture medium, placing the culture medium in an incubator at 37 ℃ for 12 hours, culturing a colony on an inoculating loop taking-out plate in 10ml of LB culture medium at 37 ℃ for 12 hours the next day, and measuring the absorbance OD 600nm =1, wherein the bacterial number concentration is about 10 9 CFU/ml, at 2000Xg centrifugal 10 minutes, remove the supernatant.
And (3) strain: taking out Escherichia coli (Escherichia coli) from a refrigerator at-80 deg.C, dipping the strain with an inoculating loop, dividing three zones on LB culture medium, placing in an incubator at 37 deg.C for 12 hours, culturing one colony on an inoculating loop taking-out plate in 10ml of LB culture medium at 37 deg.C for 12 hours the next day, and measuring absorbance OD 600nm =1, wherein the bacterial number concentration is about 10 9 CFU/ml. At this time, the bacterial solution was diluted 1000 times, 200. Mu.l of the bacterial solution was aspirated into a new centrifuge tube, and 800. Mu.l of LB medium was added, at this time, the bacterial count was about 5X 10 5 CFU/ml, was centrifuged (2000Xg, 10 min).
Blue light device and irradiation method
LED T8 lamp tube: the light wavelength is 410-510nm (lambda) max =462 nm), the power maximum is 5W.
The LED lamp tube is arranged on the polystyrene blue light making device in a pipe frame, and the distance between the LED lamp tube and a test tube to be irradiated is kept about 5mm.
Experimental procedure
Step 1, sample preparation of experimental group and control group
The 17 synthesized curcuminoids described above were weighed to 1mg, dissolved in 0.5ml of DMSO solvent, and used as a stock solution standard which accounted for DMSO 2000ppm by 100%. Mu.l of the stock solution was taken out and added to 990. Mu.l of LB medium (diluted 100-fold), 100. Mu.l of the diluted 100-fold curcuminoid was taken out and added to 900. Mu.l of LB medium (diluted 1000-fold), and 1ml of the diluted 1000-fold curcuminoid was finally taken out and added to 1ml of LB medium as a reagent to be reacted (2 ml, finally diluted 2000-fold, i.e., 1 ppm) as a test group. In addition, DMSO added with curcumin but also diluted 2000 times with LB medium was used as a comparative group, and DMSO not added with curcumin or curcuminoid but also diluted 2000 times with LB medium was used as a control group (control).
Step 2, blue light induction photosensitizer sterilization
Adding 2ml of final diluted curcuminoid into two tubes of centrifuged thallus with supernatant removed, mixing, placing in a test tube with a volume of 25 ml, placing one tube in a blue light device, irradiating for 1min, and performing spot plating. The other tube was used as control without irradiation (no light). The comparison group (i.e., with curcumin added) and the control group (i.e., without curcumin or curcuminoids added) were also formulated with two test tubes irradiated for 1 minute or not.
Step 3, dropping coating method
The reacted sample was serially diluted to 10E-7 with LB medium as solvent, 10. Mu.l each of 10E-4, 10E-5, 10E-6 and 10E-7 was dropped on LB medium, and after culturing at 37 ℃ for 12 hours, 10E-5 was counted as bacteria and the result was recorded by photographing.
Step 4, calculating the sterilization rate of the blue light and the photosensitizer
Sterilization rate = {1-T (CFU/ml) /C (CFU/ml) }×100％
Wherein T is the number of colonies in the experimental or comparative group that were not irradiated (no light) or irradiated for 1 minute (1 min), or the control was irradiated for 1 minute (1 min), and C is the number of colonies in the control group (i.e., no curcumin or curcuminoid added) that were not irradiated (no light).
Results of the experiment
A first part: staphylococcus epidermidis and Staphylococcus aureus
Referring to fig. 1, there is shown the bactericidal rate of the 17 synthetic curcuminoids against staphylococcus epidermidis in the absence/presence of photodynamic action, i.e. no blue light irradiation (no light) or blue light irradiation for 1 minute (1 min), wherein the bactericidal rate is based on the number of colonies when no curcumin or curcuminoid is added (control) and no blue light irradiation (no light) is used as a basis for calculation, and thus the value is zero. As can be seen from fig. 1, compound 2, compound 5, compound 8 and compound 9, which were irradiated for 1 minute (sample names 1 (1 min), 2 (1 min), 5 (1 min), 8 (1 min) and 9 (1 min), respectively), had significantly better bactericidal effects than the other compounds.
The inventors further conducted three more experiments on the effects of the five curcuminoids (compound 1, compound 2, compound 5, compound 8 and compound 9, respectively) having the best bactericidal effects on staphylococcus epidermidis and staphylococcus aureus, and found that compound 1, compound 8 and compound 9 all have the best bactericidal effects on staphylococcus epidermidis and staphylococcus aureus, as shown in table 1 and table 2, respectively. Wherein, the compound 8 and the compound 9 have excellent sterilization effect on staphylococcus epidermidis or staphylococcus aureus, and the sterilization rate can reach more than 99 percent. FIG. 2 is an SEM image of the effect of Compound 8 on the structure of Staphylococcus epidermidis before (a), (b) and (c) blue light irradiation at 1 minute and 5 minutes, respectively. It is evident that compound 8, when irradiated, has a killing power that causes perforation of the surface staphylococcus epidermidis.
TABLE 1 Effect of five synthetic curcuminoids on Staphylococcus epidermidis
Figure PCTCN2020114821-APPB-000008
Figure PCTCN2020114821-APPB-000009
TABLE 2 Effect of five synthetic curcuminoids on Staphylococcus aureus
Figure PCTCN2020114821-APPB-000010
Figure PCTCN2020114821-APPB-000011
Further, the sterilization test was performed following the above experimental method except that the concentrations of compound 1, compound 8 and compound 9 were reduced to 0.5ppm, and the obtained experimental results are shown in table 3. It was found that even at reduced concentrations, compounds 8 and 9 still have very good fungicidal properties.
TABLE 3 Effect of 0.5ppm concentration of Compound 1 and Compound 8 and Compound 9 on Staphylococcus epidermidis
Figure PCTCN2020114821-APPB-000012
Curcuminoid stability testing
Compound 1, compound 8 and Compound 9 were each formulated in DMSO as 2000ppm stock solutions and stored in an unirradiated room temperature (25 ℃ C.) environment. Stability assay test these stock standards were further diluted 100-fold in DMSO (i.e., 20 ppm) and allowed to stand for 48 hours, after which a slight change in color was observed with the naked eye for Compound 1, but not for Compound 8 and 9. Mu.l of each compound was taken and measured for absorbance at 220-750nm on a spectrophotometer. As shown in the results of fig. 3, the absorbance at the maximum wavelength was decreased by about 0.8% and 1.3% for compound 8 (maximum absorption wavelength 440 nm) and compound 9 (maximum absorption wavelength 426 nm) (shown in fig. (b) and (c), respectively), while the absorbance at the maximum wavelength was decreased by about 6.4% for compound 1 (maximum absorption wavelength 426 nm). Therefore, according to this result, it was found that compound 8 and compound 9 had better stability than compound 1.
A second part: escherichia coli
The curcuminoid compound 8 having an excellent bactericidal effect against both staphylococcus epidermidis and staphylococcus aureus was further investigated for its effect on escherichia coli.
The method comprises the following steps: the stock solution standard was diluted 2000-fold and the bacterial count concentration was about 10 9 CFU/ml
As described in step 1 above, compound 8 was weighed at 1mgDissolved in 0.5ml of DMSO solvent, and diluted 2000-fold with LB medium as a reagent to be reacted (1 ppm) as a stock solution standard which accounts for 100% DMSO of 2000 ppm. In addition, in the case of E.coli culture, as described in the above-mentioned strain 3, the absorbance OD 600nm =1 was measured, and then centrifugation was carried out at 2000Xg for 10 minutes to remove the supernatant, thereby obtaining the bacterial count concentration of about 10 9 CFU/ml. The control group was identical to the experimental group except that compound 8 was not added, and the subsequent experimental procedures were the same as those of steps 2 to 4 described above. The results are shown in Table 4, and under these conditions, compound 8 has a limited bactericidal effect on E.coli.
TABLE 4 photodynamic bactericidal effect of curcuminoid compound 8 (1 ppm) on E.coli
Figure PCTCN2020114821-APPB-000013
The second method comprises the following steps: the stock solution standard was diluted 1000-fold and the bacterial count concentration was about 10 9 CFU/ml
As described in the above step 1, compound 8 was weighed at 1mg, dissolved in 0.5ml of DMSO solvent as a stock solution standard in 100% DMSO 200ppm, and diluted 1000-fold by LB medium as a reagent to be reacted. In addition, escherichia coli was cultured as described in the above strain 3, and the absorbance OD 600nm =1 was measured, and then centrifuged at 2000Xg for 10 minutes to remove the supernatant, thereby obtaining a bacterial count concentration of about 10 9 CFU/ml. The control group was identical to the experimental group except that compound 8 was not added, and the subsequent experimental procedures were the same as those of steps 2 to 4 described above. Method two further increased the concentration of curcuminoid compound 8 to 2ppm compared to method one, and the experimental results are shown in table 5. Under the condition, the bactericidal effect of the compound 8 on the escherichia coli is slightly improved.
TABLE 5 photodynamic bactericidal effect of curcuminoid compound 8 (2 ppm) on E.coli
Figure PCTCN2020114821-APPB-000014
The foregoing is illustrative only and is not limiting. Any equivalent modifications or variations without departing from the spirit and scope of the present invention should be included in the scope of the appended claims.

Claims (12)

  1. A fungicide comprising a compound represented by formula I:
    Figure PCTCN2020114821-APPB-100001
    wherein the content of the first and second substances,
    Ar 1 and Ar 2 Each independently is a phenyl, naphthyl, thienyl, furyl or pyridyl group, unsubstituted or substituted by a substituent, and Ar 1 And Ar 2 The same or different;
    the substituent is selected from the group consisting of halogen, hydroxyl, alkyl and alkoxy;
    when Ar is 1 And Ar 2 When each is independently phenyl substituted with two substituents, ar 1 And Ar 2 Different.
  2. The fungicide according to claim 1, wherein the compound of formula I is selected from at least one of the following compounds 1 to 11:
    Figure PCTCN2020114821-APPB-100002
    Figure PCTCN2020114821-APPB-100003
  3. a bactericidal agent as claimed in claim 1, wherein the species that is suppressible and/or killable comprises aerobic species.
  4. A bactericidal agent according to claim 1 wherein the species that is inhibited and/or killed comprises gram positive bacteria.
  5. The bactericidal agent of claim 4, wherein the gram-positive bacteria comprises Staphylococcus epidermidis or Staphylococcus aureus.
  6. The bactericide as claimed in claim 1, wherein the concentration of the compound represented by the formula I is 0.5ppm to 1ppm.
  7. A method of sterilization, comprising:
    contacting a compound shown in a chemical formula I with a strain; and
    irradiating the compound with a light source having a wavelength in the blue range;
    Figure PCTCN2020114821-APPB-100004
    wherein the content of the first and second substances,
    Ar 1 and Ar 2 Each independently is a phenyl, naphthyl, thienyl, furyl or pyridyl group, unsubstituted or substituted by a substituent, and Ar 1 And Ar 2 The same or different;
    the substituent is selected from the group consisting of halogen, hydroxyl, alkyl and alkoxy;
    when Ar is 1 And Ar 2 When each is independently phenyl substituted with two substituents, ar 1 And Ar 2 Different.
  8. The method of claim 7, wherein the compound of formula I is selected from at least one of the following compounds 1 to 11:
    Figure PCTCN2020114821-APPB-100005
  9. the method of claim 7, wherein the species comprises an aerobic species.
  10. The method of claim 7, wherein the species comprises a gram-positive bacterium.
  11. The method of claim 10, wherein the gram-positive bacteria comprises staphylococcus epidermidis or staphylococcus aureus.
  12. The method of claim 7, wherein the concentration of the compound of formula I is 0.5ppm to 1ppm.
CN202080102727.4A 2020-09-11 2020-09-11 Bactericide and method of sterilizing Pending CN115803310A (en)

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