KR102029922B1 - Antimicrobial composition and antifungal composition comprising a compound having anhydrosugar alcohol core and alkylene oxide extender and formulation comprising the same - Google Patents

Abstract

The present invention relates to an antimicrobial composition, an antifungal composition comprising a compound having an anhydrosugar alcohol nucleus and an alkylene oxide extension, and an agent comprising the same, and more particularly, to excellent growth inhibition of microorganisms including bacteria and fungi. By including a compound having an anhydrous sugar alcohol nucleus and an alkylene oxide extension that exhibits an effect, antimicrobial compositions, antifungal compositions, and the like, which can be used in various products such as cosmetics, skin cosmetics, detergents, colorants, paints and plant protection agents It relates to a formulation.

Description

FIELD OF THE INVENTION An antimicrobial composition comprising an anhydrosugar alcohol nucleus and a compound having an alkylene oxide extension, an antifungal composition and a formulation comprising the same.

The present invention relates to an antimicrobial composition, an antifungal composition comprising a compound having an anhydrosugar alcohol nucleus and an alkylene oxide extension, and an agent comprising the same, and more particularly, to excellent growth inhibition of microorganisms including bacteria and fungi. By including a compound having an anhydrous sugar alcohol nucleus and an alkylene oxide extension that exhibits an effect, antimicrobial compositions, antifungal compositions, and the like, which can be used in various products such as cosmetics, skin cosmetics, detergents, colorants, paints and plant protection agents It relates to a formulation.

Hydrogenated sugar (also called “sugar alcohol”) means a compound obtained by adding hydrogen to a reducing end group of a saccharide, and generally HOCH ₂ (CHOH) _n CH ₂ OH (where n is an integer of 2 to 5). ) And are classified according to carbon number to trititol, pentitol, hexitol and heptitol (4, 5, 6 and 7 carbon atoms, respectively). Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol and the like, and sorbitol and mannitol are particularly useful substances.

Anhydrosugar alcohols have a diol form having two hydroxyl groups in the molecule, and may be prepared using hexitol derived from starch (eg, Korean Patent No. 10-1079518, Korean Patent Publication No. 10). -2012-0066904). Anhydrosugar alcohols have been studied for a long time with a great deal of interest in that they are environmentally friendly materials derived from renewable natural resources. Among these anhydrosugar alcohols, isosorbide made from sorbitol has the widest range of industrial applications at present.

The use of anhydrosugar alcohols is very diverse, such as treatment of heart and vascular diseases, adhesives of patches, mouthwashes and the like, solvents of the composition in the cosmetic industry, emulsifiers in the food industry. In addition, it is possible to raise the glass transition temperature of polymer materials such as polyester, PET, polycarbonate, polyurethane, epoxy resin, improve the strength of these materials, and because it is an eco-friendly material derived from natural products, useful. In addition, it is known that it can also be used as an environmentally friendly solvent of adhesives, environmentally friendly plasticizers, biodegradable polymers, water-soluble lacquer.

In recent years, with interest in environmental protection, and interest in antimicrobial treatment, antifungal treatment and long-term preservation of products, bio-based antimicrobial composition and antifungal composition by utilizing the microbial growth inhibitory effect of anhydrosugar alcohols derived from plants It is necessary to develop.

An object of the present invention is to include a compound having an anhydrosugar alcohol nucleus and an alkylene oxide extension which exhibits an excellent effect on inhibiting the growth of microorganisms including bacteria and fungi, thereby making up cosmetics, skin cosmetics, cleaning agents, coloring agents, paints and plant protection agents. It is to provide an antimicrobial composition, antifungal composition and formulations containing the same that can be used in various products such as.

The present invention to solve the above technical problem, provides an antimicrobial composition comprising a compound represented by the formula (A):

[Formula A]

X-Y-O-M-O-Y’-X

In Chemical Formula A,

Each X is independently —CH ₂ NH ₂ ,

Y is-[CH ₂ CHR ₁ O] _m -CHR ₂ CHR _3- ,

Y 'is-[CH ₂ CHR ₁ O] _n -CHR ₂ CHR _3- ,

Wherein R ₁ is each independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer from 1 to 25,

M is a divalent organic group derived from anhydrosugar alcohol.

According to another aspect of the present invention, there is provided an antifungal composition comprising a compound represented by the following formula (A):

[Formula A]

X-Y-O-M-O-Y’-X

In Chemical Formula A,

Each X is independently —CH ₂ NH ₂ ,

Y is-[CH ₂ CHR ₁ O] _m -CHR ₂ CHR _3- ,

Y 'is-[CH ₂ CHR ₁ O] _n -CHR ₂ CHR _3- ,

Wherein R ₁ is each independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer from 1 to 25,

M is a divalent organic group derived from anhydrosugar alcohol.

According to another aspect of the invention, there is provided a formulation comprising the antimicrobial composition, the antifungal composition, or a combination thereof.

The antimicrobial and antifungal compositions of the present invention comprise compounds having anhydrosugar alcohol nuclei and alkylene oxide extensions that are prepared from renewable plant-based low cost raw materials and exhibit excellent effects on the growth inhibition of microorganisms including bacteria and fungi. Because it contains, it can be used in a variety of products, such as cosmetics, skin cosmetics, cleaning agents, colorants, paints and plant protection agents as an environmentally friendly preservative.

Hereinafter, the present invention will be described in detail.

The present invention to solve the above technical problem, provides an antimicrobial composition comprising a compound represented by the formula (A):

[Formula A]

X-Y-O-M-O-Y’-X

In Chemical Formula A,

Each X is independently —CH ₂ NH ₂ ,

Y is-[CH ₂ CHR ₁ O] _m -CHR ₂ CHR _3- ,

Y 'is-[CH ₂ CHR ₁ O] _n -CHR ₂ CHR _3- ,

Wherein R ₁ is each independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer from 1 to 25,

M is a divalent organic group derived from anhydrosugar alcohol.

The present invention also provides an antifungal composition comprising the compound represented by Formula (A).

Compounds having anhydrosugar alcohol nuclei included in the antimicrobial composition and antifungal composition of the present invention are prepared from low-cost raw materials based on renewable plants, and exhibit excellent effects on the growth inhibition of microorganisms including bacteria and fungi. It can be used as a preservative in such products. The compositions of the present invention exhibit antifungal as well as antimicrobial properties and can be used in a variety of formulations.

The anhydrosugar alcohol is prepared from hydrogenated sugars derived from natural products.

Hydrogenated sugar (also called “sugar alcohol”) means a compound obtained by adding hydrogen to a reducing end group of a saccharide, and generally HOCH ₂ (CHOH) _n CH ₂ OH (where n is an integer of 2 to 5). ) And are classified according to carbon number to trititol, pentitol, hexitol and heptitol (4, 5, 6 and 7 carbon atoms, respectively).

Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol and the like, and sorbitol and mannitol are particularly useful substances.

Anhydrosugar alcohols have a diol form having two hydroxyl groups in the molecule, and may be prepared using hexitol derived from starch (eg, Korean Patent No. 10-1079518, Korean Patent Publication No. 10). -2012-0066904). Anhydrosugar alcohols have been studied for a long time with a great deal of interest in that they are environmentally friendly materials derived from renewable natural resources. Among these anhydrosugar alcohols, isosorbide made from sorbitol has the widest range of industrial applications at present.

In the compound represented by the formula (A) of the present invention, M is isosorbide (1,4-3,6- dianhydrosorbitol) and isomannide (1,4-3,6- dianhydromannitol) which are anhydrosugar alcohols. Or a divalent organic group derived from isoidide (1,4-3,6- dianhydroiditol), and in one embodiment, M may be selected from the following formulas.

In the compound represented by the formula (A) of the present invention, R ₁ is each independently hydrogen, alkyl or aryl, and R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl.

The alkyl is, for example, substituted or unsubstituted linear alkyl having 1 to 10 carbon atoms (more specifically 1 to 6); Or substituted or unsubstituted C3 to 10 (more specifically 3 to 6) branched alkyl, wherein the aryl is, for example, substituted or unsubstituted C6 to 14 (more specifically 6 to 12). Monocyclic aryl, polycyclic aryl, or fused cyclic aryl. In addition, the heteroaryl is a substituted or unsubstituted 5- to 12-membered (more specifically 5- to 10-membered) monocyclic hetero, including for example one or more hetero atoms selected from N, O, S Aryl, polycyclic heteroaryl, or fused cyclic heteroaryl, wherein the cycloalkyl may be, for example, substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms (more specifically 3 to 6).

The groups may be, for example, one or more substituents selected from alkyl having 1 to 10 carbon atoms (eg, methyl, ethyl, propyl, butyl, etc.) or aryl having 6 to 10 carbon atoms (eg, phenyl, benzyl, tolyl, etc.). Can be substituted.

In one embodiment, the compound represented by Formula A of the present invention may be a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Each R ₁ is independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer of 1-25.

In another embodiment, the compound represented by Formula A of the present invention may be a compound represented by Formula 2:

[Formula 2]

In Chemical Formula 2,

Each R ₁ is independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer of 1-25.

In another embodiment, the compound represented by Formula A of the present invention may be a compound represented by Formula 3:

[Formula 3]

In Chemical Formula 3,

Each R ₁ is independently hydrogen, alkyl or aryl,

R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,

m and n are each independently an integer of 0 to 15,

m + n is an integer of 1-25.

The content of the compound represented by Formula A included in the antimicrobial composition of the present invention may be 0.01 to 30 wt% based on 100 wt% of the antimicrobial composition. For example, the lower limit of the content of the compound represented by the formula (A) is 0.01% by weight, 0.05% by weight, 0.1% by weight, 1% by weight, 3% by weight, 5% by weight or more based on 100% by weight of the antimicrobial composition. , At least 7 wt%, at least 10 wt%, at least 15 wt% or at least 20 wt%. In addition, the upper limit of the content of the compound represented by the formula (A) is 30% by weight, 20% by weight, 15% by weight, 10% by weight, 9% by weight, 8.5% by weight or less based on 100% by weight of the antimicrobial composition. , 8 wt% or less, 7 wt% or less, 5 wt% or less, or 3 wt% or less. When the content of the compound represented by Formula A is lower than the numerical range, the effect of inhibiting the growth of microorganisms (specifically, bacteria) may be insignificant. On the contrary, when the content is higher than the numerical range, additional effects may not be obtained.

The antimicrobial composition of the present invention is phenoxyethanol, alkanediol, methylchloroisothiazolinone, methylisothiazolinone, benzoic acid or salts thereof, benzoic acid ester derivatives, salicylic acid or salts thereof, 4-hydroxy benzoic acid or salts thereof, Sorbic acid or salts thereof, dehydroacetic acid or salts thereof, dehydroacetic acid ester derivatives, phenoxyethanol, benzyl alcohol, 2-methylisothiazol-3 (2H) -one, 4-isopropyl-m-cresol, or It may further comprise one or more additives selected from the group consisting of zinc pyrithione. Although not particularly limited, the content of the additive is based on 100% by weight of the antimicrobial composition, such as 0.1 to 50% by weight, for example, 0.5% by weight or more, 1% by weight or more, 5% by weight, 10% by weight or more, 20% by weight or more Or 30 wt% or more, and may be 45 wt% or less, 40 wt% or less, 35 wt% or less, 30 wt% or less, 20 wt% or less, or 15 wt% or less.

The content of the compound represented by Formula A included in the antifungal composition of the present invention may be 0.005 to 30% by weight based on 100% by weight of the antifungal composition. For example, the lower limit of the amount of the compound represented by the formula (A) is 0.005% by weight, 0.01% by weight, 0.05% by weight, 0.1% by weight, 1% by weight, 3% by weight based on 100% by weight of the antifungal composition. Or at least 5 wt%, at least 7 wt%, at least 10 wt%, at least 15 wt% or at least 20 wt%. In addition, the upper limit of the content of the compound represented by the formula (A) is 30 wt% or less, 20 wt% or less, 15 wt% or less, 10 wt% or less, 9 wt% or less, 8.5 wt% based on 100 wt% of the antifungal composition. Up to 8 wt%, up to 7 wt%, up to 5 wt% or up to 3 wt%. When the content of the compound represented by the formula (A) is lower than the numerical range, the effect of inhibiting the growth of microorganisms (specifically fungi) may be insignificant. On the contrary, when the content is higher than the numerical range, additional effects may not be obtained.

The antifungal composition of the present invention is phenoxyethanol, alkanediol, methylchloroisothiazolinone, methylisothiazolinone, benzoic acid or salts thereof, benzoic acid ester derivatives, salicylic acid or salts thereof, 4-hydroxy benzoic acid or salts thereof Sorbic acid or salts thereof, dehydroacetic acid or salts thereof, dehydroacetic acid ester derivatives, phenoxyethanol, benzyl alcohol, 2-methylisothiazol-3 (2H) -one, 4-isopropyl-m-cresol, Or one or more additives selected from the group consisting of zinc pyrithione. Although not particularly limited, the content of the additive is based on 100% by weight of the antifungal composition, such as 0.1 to 50% by weight, for example, 0.5% by weight, 1% by weight, 5% by weight, 10% by weight, 20% by weight. Or at least 30% by weight, and at most 45%, at most 40%, at most 35%, at most 30%, at most 20%, or at most 15%.

According to another aspect of the invention, there is provided a formulation comprising said antimicrobial composition, antifungal composition or a combination thereof.

The antimicrobial composition and antifungal composition of the present invention have an excellent effect on the inhibition of microbial growth through the measurement of minimal inhibitory concentration (MIC) for a number of bacteria and fungi, as described in the examples below. As confirmed, it can be included as a preservative in various products. Formulations comprising an antimicrobial composition, antifungal composition or a combination thereof of the present invention may be, for example, a formulation selected from the group consisting of cosmetics, skin cosmetics, cleaning agents, coloring agents, paints and plant protection agents, but is not limited thereto. It doesn't work.

Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the scope of the present invention is not limited to these.

[ Example ]

[ Production Example  One]

Strain Culture (Activation)

Before the antimicrobial and antifungal activity test, the culture was carried out several times to increase the activity of the bacteria.

Bacteria were streaked on a NutrientAgar (NA) plate having the ingredients and contents shown in Table 1 below, cultured in a 37 ° C. incubator until colonies were identified, and colonies randomly selected after confirming colony contamination. In addition, it was cultured under the same conditions again to increase the activity of the bacteria.

The fungi were streaked identically on a Potato Dextrose Agar (PDA) plate having the ingredients and contents shown in Table 2 below, followed by culturing until growth was confirmed in a 30 ° C. incubator, and then checked for contamination and the randomly selected colonies again under the same conditions. Incubated at to increase the activity of the bacteria.

Anhydrosugar  Alcohol nuclei and alkylene Oxide Extension  Preparation of containing compound containing culture

After preparing the liquid medium according to the type of strain, the compounds of the above formulas 1 to 3 were added to each of the liquid medium to 1%, 2.5%, 5%, 7.5% and 10% by weight. Specifically, in Formulas 1 to 3, i) when R ₁ = R ₂ = R ₃ = H, m + n = 5, ii) R ₁ = R ₂ = H, R ₃ = CH ₃ , m + n = 20 Iii) R ₁ = CH ₃ , R ₂ = R ₃ = H, m + n = 3 and iv) R ₁ = CH ₃ , R ₂ = Ph, R ₃ = H, m + n = 10 The compound in case of was used.

For bacteria, Tryptic Soy Broth (TSB) having the components and contents of Table 3 was used as a liquid medium, and Potato Dextrose Broth (PDB) having the components and contents of Table 4 was used as a liquid medium for fungi. Liquid medium containing compounds with anhydrosugar alcohol nuclei and alkylene oxide extensions were prepared by dispensing into 14 ml test tubes.

inoculation Fungus  Preparations

Each colony activated by culturing in an Agar plate was used as an inoculation bacterium for inoculating a culture solution containing a compound of Formulas 1 to 3 after confirming morphological characteristics to confirm additional external contamination. Each strain was diluted with 9 ml physiological saline by using a colony of platinum. The dilution concentration at this time was adjusted to the value of McFarland standard 0.5. When the McFarland standard was adjusted to 0.5, the concentration of cells in physiological saline was 1.5 x 10 ⁸ CFU / ml.

Inoculation and Cultivation

Into each of the concentration of 3 ml of the medium containing the compound of the formula 1 to 3, 30 μl of each bacterium in which the concentration was adjusted was added, and the bacterial solution was inoculated by diluting to 1/100. Inoculated bacteria were incubated at 200 rpm for 24 hours at 37 ℃, inoculated fungi were incubated at 200 rpm for 72 hours at 30 ℃.

Confirmation of inoculation cell growth (preliminary test)

In order to simply check the growth of cells in the inoculated culture, streaking was performed on an Agar plate. Some of the bacterial cultures grown for 24 hours and some of the fungal cultures grown for 72 hours using platinum were streaked on Tryptic Soy Agar (TSA) plates and Potato Dextrose Agar (PDA) plates, respectively, and then 37 and 30 ° C, respectively. The culture was performed until the growth of bacteria was confirmed. Specifically, when the bacteria were incubated for 24 hours, the growth of the bacteria was confirmed, and the fungi were able to confirm the growth of the bacteria when they were cultured for 72 hours. After streaking and cultured, it was possible to simply check the growth, and to reset the concentration of the compound of Formulas 1 to 3.

Minimum growth inhibition concentration ( MIC ) Judgment

Experiments were performed to set the minimum growth inhibition concentration (MIC) based on the concentrations set through the preliminary tests. The bacterial solution was inoculated into a liquid medium containing a compound of Formulas 1 to 3 at a set concentration. The liquid medium containing the compounds of Formulas 1 to 3 was carried out by adding 3 ml in a 14 ml test tube, and the inoculum bacteria were prepared and used in the same manner as in the above inoculation solution preparation (1.5 x 10 ⁸ CFU in physiological saline). bacteria solution to a concentration of / ml). After inoculating 30 μl of the bacterial solution into the liquid medium, the bacteria were incubated at 37 ° C. for 24 hours, and the fungi were incubated at 30 ° C. for 72 hours. After incubation, the culture was plated on an Agar plate to check the growth of bacteria. Specifically, the bacteria were plated on a NutrientAgar (NA) plate, and the fungi were plated on a Potato Dextrose Agar (PDA) plate, and unlike the preliminary test, the colony was confirmed. After incubation by concentration, the concentration when colonies were not produced was set to the minimum growth inhibition concentration (MIC).

[ Example  1] Preliminary test of 3 bacteria and 2 fungi

Pseudomonas as three bacteria aeruginosa KCTC 2513, Staphylococcus aureussubsp. aureus KCTC 3881 and Escherichia coli was used, and after their activation, bacterial solutions were prepared according to McFarland standard 0.5. The bacteria solution was inoculated in Tryptic Soy Broth to which the compounds of Formulas 1 to 3 were added, and then cultured at 200 rpm at 30 ° C. for 24 hours. After cultured for 24 hours on a Nutrient Agar (NA) plate streaked, it was confirmed whether the growth by concentration (the concentration is the weight percent of the compound of formula 1 to 3 based on 100% by weight of the total culture medium).

Candida as two fungi albicans and Aspergillus niger were used, and after their activation, bacterial solutions were prepared according to McFarland standard 0.5. The bacteria solution was inoculated in Potato Dextrose Broth to which the compounds of Formulas 1 to 3 were added, and then cultured at 200 rpm at 30 ° C. for 72 hours. After culturing for 72 hours, the culture solution was streaked on a Potato Dextrose Agar plate, and then the growth of each concentration was determined (the concentration is the weight% of the compound of Chemical Formulas 1 to 3 based on 100% by weight of the culture medium).

As a result, as can be seen in Tables 5 to 16, the compounds of Formulas 1 to 3 exhibit antimicrobial activity against three bacteria and antifungal activity against two fungi regardless of high and low concentrations throughout various substituent structures. Showed.

[ Example  2] 3 bacteria and 2 fungi MIC  Test

Based on the preliminary test results of Example 1, the concentration range of the compound of Formulas 1 to 3 was set to proceed with the MIC test. The concentration range of the compound of Formulas 1 to 3 was set to 1,000 to 20,000 ppm, and then the experiment was conducted. MIC test results show that the antimicrobial activity is excellent in the presence of at least 10,000 ppm or more of the compound of Formulas 1 to 3, and the antibacterial activity is good in the presence of at least 5,000 ppm or more of the compound of Formulas 1 to 3, depending on the strain and the compound of Formulas 1 to 3. Confirmed.

Claims (18)

An antimicrobial composition comprising a compound represented by formula (A):
[Formula A]
XYOMO-Y'-X
In Formula A,
Each X is independently —CH ₂ NH ₂ ,
Y is-[CH ₂ CHR ₁ O] _m -CHR ₂ CHR _3- ,
Y 'is-[CH ₂ CHR ₁ O] _n -CHR ₂ CHR _3- ,
Wherein R ₁ is each independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer from 1 to 25,
M is a divalent organic group derived from isosorbide, isomannide, or isoidide. delete The antimicrobial composition of claim 1 wherein M is selected from the formula:

According to claim 1, Antimicrobial composition comprising a compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antimicrobial composition of claim 1 comprising a compound represented by the following Chemical Formula 2:
[Formula 2]

In Chemical Formula 2,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antimicrobial composition of claim 1 comprising a compound represented by the following Chemical Formula 3:
[Formula 3]

In Chemical Formula 3,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antimicrobial composition of claim 1, wherein the content of the compound represented by Formula A is 0.01 to 30 wt% based on 100 wt% of the antimicrobial composition. The phenoxyethanol, alkanediol, methylchloroisothiazolinone, methylisothiazolinone, benzoic acid or salts thereof, benzoic acid ester, salicylic acid or salts thereof, 4-hydroxy benzoic acid or salts thereof, sorbic acid Or a salt thereof, dehydroacetic acid or a salt thereof, dehydroacetic acid ester, benzyl alcohol, 2-methylisothiazol-3 (2H) -one, 4-isopropyl-m-cresol, or zinc pyrithione The antimicrobial composition further comprises one or more additives selected. An antifungal composition comprising a compound represented by formula (A):
[Formula A]
XYOMO-Y'-X
In Formula A,
Each X is independently —CH ₂ NH ₂ ,
Y is-[CH ₂ CHR ₁ O] _m -CHR ₂ CHR _3- ,
Y 'is-[CH ₂ CHR ₁ O] _n -CHR ₂ CHR _3- ,
Wherein R ₁ is each independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer from 1 to 25,
M is a divalent organic group derived from isosorbide, isomannide, or isoidide. delete The antifungal composition of claim 9, wherein M is selected from the formula:

The antifungal composition of claim 9 comprising the compound represented by Formula 1 below:
[Formula 1]

In Chemical Formula 1,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antifungal composition of claim 9 comprising a compound represented by the following Chemical Formula 2:
[Formula 2]

In Chemical Formula 2,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antifungal composition of claim 9 comprising the compound represented by the following formula (3):
[Formula 3]

In Chemical Formula 3,
Each R ₁ is independently hydrogen, alkyl or aryl,
R ₂ and R ₃ are each independently hydrogen, alkyl, aryl, heteroaryl or cycloalkyl,
m and n are each independently an integer of 0 to 15,
m + n is an integer of 1-25. The antifungal composition of claim 9, wherein the content of the compound represented by Formula A is 0.005 to 30 wt% based on 100 wt% of the antifungal composition. The method of claim 9, wherein the phenoxyethanol, alkanediol, methylchloroisothiazolinone, methylisothiazolinone, benzoic acid or salts thereof, benzoic acid esters, salicylic acid or salts thereof, 4-hydroxy benzoic acid or salts thereof, sorbic acid Or a salt thereof, dehydroacetic acid or a salt thereof, dehydroacetic acid ester, benzyl alcohol, 2-methylisothiazol-3 (2H) -one, 4-isopropyl-m-cresol, or zinc pyrithione An antifungal composition further comprising one or more additives selected. A formulation comprising an antimicrobial composition according to any one of claims 1 and 3 to 8 or an antifungal composition according to any one of claims 9 and 11 to 16. 18. The formulation according to claim 17, wherein the formulation is selected from the group consisting of cosmetics, skin cosmetics, detergents, colorants, paints or plant protection agents.