JP2014136690A - Powdery antifungal agent composition, and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a powdery antifungal agent composition prevented from booking and melting which is used for preventing contamination by microorganisms such as molds in the industrial filed.SOLUTION: A powdery composition contains at least one compound selected from the group consisting of iodoalkynyl compounds represented by formula (1), and at least one compound selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds, and does not contain a water-insoluble inorganic carrier. In the formula (1), R is a hydrogen, an n-valent saturated hydrocarbon group, or the like, m is a number of methylene groups in the parenthesis and is any integer of 1-3, and n is a number of groups binding to R in the parenthesis and is any integer of 1-3.

Description

  The present invention relates to a powdery fungicide composition and a method for producing the same. More specifically, the present invention contains an iodoalkynyl compound that is used in the industrial field for preventing fouling by microorganisms such as fungi and does not easily block during storage without containing a water-insoluble inorganic carrier. The present invention relates to a powdery fungicide composition and a method for producing the same.

  Various industrial water used in papermaking process, pulp manufacturing process, cooling water circulation process, etc .; metal processing oil such as cutting oil; wood, casein, starch paste, glue, coated paper, paper coating liquid, surface size Various industrial products such as adhesives, paints, adhesives, synthetic rubber latex, inks, polyvinyl alcohol films, vinyl chloride films, resin products, cement admixtures, sealing agents, and joint agents include bacteria, molds, yeasts, and algae. Microorganisms are easy to propagate. When microorganisms propagate, harmful effects such as a decrease in productivity, a decrease in quality, and a generation of malodors occur. Therefore, various anti-fungal agents, bactericides, antibacterial agents and the like are used to suppress and control the growth of such microorganisms.

  As one of the active ingredients used for such drugs, iodoalkynyl compounds such as 3-iodo-2-propynyl-N-butylcarbamate (hereinafter sometimes abbreviated as IPBC) are known. IPBC not only prevents the germination of mold spores but also has a high effect of preventing the growth of mold after germination. Further, for the purpose of expanding the antibacterial spectrum and preventing the appearance of resistant bacteria, a mixture of two or more active ingredients, for example, a bactericidal active compound and a fungicidal active compound has been proposed.

  IPBC itself is prone to degradation during storage. In addition, when an iodoalkynyl compound such as IPBC is mixed with other pest control agents, the melting point may be significantly lowered. Therefore, the iodoalkynyl compound in a powder state is likely to be blocked by compression or by long-term storage. The blocked iodoalkynyl compound may cause problems in dry pulverization or wet pulverization, and its handling property is difficult. Various proposals have been made to solve these problems.

  For example, Patent Document 1 describes a bactericidal composition containing IPBC, white carbon, and methyl 2-benzimidazolecarbamate or 2- (thiazol-4-yl) benzimidazole. Patent Document 1 states that decomposition of IPBC can be suppressed by this sterilizing composition. Patent Document 2 states that blocking can be suppressed by adding white carbon to micronized IPBC. Patent Document 3 states that IPBC blocking can be suppressed by mixing IPBC and a solid support under heating. Patent document 4 is disclosing the powdery formulation containing IPBC and a specific kind of talc. According to Patent Document 4, this powdery formulation seems to have excellent fluidity because IPBC in the formulation is stabilized.

Japanese Patent Laid-Open No. 2-164803 JP 2000-273008 A JP 2001-270804 A JP 2004-161663 A

  In the preparation disclosed in the patent document, a water-insoluble inorganic carrier such as talc or white carbon is used to suppress blocking. The use of water-insoluble inorganic carriers may cause inconveniences depending on the application, and depending on the types of active ingredients that coexist, the chemical stability of the active ingredients may be affected. is there.

  An object of the present invention is to provide a powdery fungicide composition containing an iodoalkynyl compound that does not easily cause blocking during storage without containing a water-insoluble inorganic carrier.

  The inventors of the present invention have made extensive studies in order to achieve the above object. As a result, at least one selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds or a pest control substance having a melting point of 200 ° C. or higher. When at least one selected from the group consisting of iodoalkynyl compounds such as IPBC is added to at least one selected from the group consisting of iodoalkynyl compounds, it is difficult to cause blocking during storage without adding a water-insoluble inorganic carrier. It has been found that a powdery fungicide composition containing a compound can be obtained. The present invention has been completed based on this finding.

That is, the present invention includes the following aspects.
[1] At least one selected from the group consisting of iodoalkynyl compounds represented by formula (1);
A powdery fungicide composition containing at least one selected from the group consisting of a benzimidazole compound and an isophthalonitrile compound and containing no water-insoluble inorganic carrier.

式（１）中、Ｒは、水素原子、無置換の若しくは置換基を有する炭素数１〜２０のｎ価の脂肪族飽和炭化水素基、無置換の若しくは置換基を有する炭素数６〜２０のｎ価の芳香族炭化水素基、または無置換の若しくは置換基を有する炭素数６〜２０のｎ価の芳香環で置換された脂肪族炭化水素基、無置換の若しくは置換基を有する炭素数３〜１０のｎ価の脂環式飽和炭化水素基、または無置換の若しくは置換基を有する炭素数３〜１０のｎ価の脂環式不飽和炭化水素基を示す。ｍは括弧内のメチレン基の数を示し且つ１〜３のいずれかの整数である。ｎはＲと結合する括弧内の基の数を示し且つ１〜３のいずれかの整数である。

In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. an n-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number 3 10 to 10 n-valent alicyclic saturated hydrocarbon group, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms. m represents the number of methylene groups in parentheses and is an integer of 1 to 3. n shows the number of the group in the parenthesis couple | bonded with R, and is an integer in any one of 1-3.

[2] Contains at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1) and at least one selected from the group consisting of pest control substances having a melting point of 200 ° C. or higher, and is insoluble in water. A powdery fungicide composition containing no inorganic carrier.
[3] The powdery antifungal agent composition according to [1] or [2], wherein the iodoalkynyl compound is 3-iodo-2-propynyl-N-butylcarbamate.
[4] The powdery antifungal agent composition according to [1], wherein the benzimidazole compound is methyl benzimidazol-2-ylcarbamate.
[5] The powdery antifungal agent composition according to [1], wherein the isophthalonitrile compound is 2,4,5,6-tetrachloroisophthalonitrile.

[6] including adding at least one selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds to at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1) A method for preventing blocking of a powder containing an iodoalkynyl compound.
[7] Adding at least one selected from the group consisting of pesticidal substances having a melting point of 200 ° C. or higher to at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1) A method for preventing blocking of a powder containing an iodoalkynyl compound.
[8] including mixing at least one selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds and at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1) , [1] The manufacturing method of the powdery antifungal agent composition.
[9] including mixing at least one selected from the group consisting of pest control substances having a melting point of 200 ° C. or higher and at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1) The manufacturing method of the powdery antifungal agent composition as described in [2].

  According to the present invention, powders containing an iodoalkynyl compound that are used in the industrial field for preventing fouling by microorganisms such as molds and hardly contain blocking during storage without containing a water-insoluble inorganic carrier. An antifungal composition is provided.

  The powdery fungicide composition according to one embodiment of the present invention comprises at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1), a benzimidazole compound and an isophthalonitrile compound. It contains at least one selected from the group and does not contain a water-insoluble inorganic carrier.

  The iodoalkynyl compound used in the present invention is a compound represented by the formula (1). In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. an n-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number 3 10 to 10 n-valent alicyclic saturated hydrocarbon group, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms. m represents the number of methylene groups in parentheses and is an integer of 1 to 3. n shows the number of the group in the parenthesis couple | bonded with R, and is an integer in any one of 1-3. R is an n-valent group.

First, the term “unsubstituted” means only the group serving as the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure as the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C 1-6” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of groups that can be “substituents” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n-propyl, i-propyl, n-butyl, and s-butyl. A C1-6 alkyl group such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; C3-6 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group C2-6 alkenyl groups such as nyl group, 3-hexenyl group, 4-hexenyl group and 5-hexenyl group; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group and 3-cyclohexenyl group Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl Group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group A C2-6 alkynyl group such as;

  C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy group and butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryl groups such as phenyl group and naphthyl group; phenoxy group and 1-naphthoxy group A C7-11 aralkyl group such as a benzyl group or a phenethyl group; a C7-11 aralkyloxy group such as a benzyloxy group or a phenethyloxy group; a formyl group, an acetyl group, a propionyl group, a benzoyl group, C1- such as a cyclohexylcarbonyl group Acyl group; C1-7 acyloxy group such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group A C1-6 alkoxycarbonyl group such as n-butoxycarbonyl group or t-butoxycarbonyl group; a carboxyl group;

  Oxy group; C 1-6 haloalkyl such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group Group; C2-6 haloalkenyl group such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5- C2-6 haloalkynyl group such as bromo-2-pentynyl group; C1-6 haloalkoxy group such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group, 3-bromo C2-6 haloalkenyloxy groups such as butenyloxy group; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophen C6-10 haloaryl group such as 4-fluorophenyloxy group, C6-10 haloaryloxy group such as 4-chloro-1-naphthoxy group; chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4- A C1-7 haloacyl group such as a chlorobenzoyl group;

  Cyano group; isocyano group; nitro group; isocyanato group; cyanato group; azide group; amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group and diethylamino group; C6- such as anilino group and naphthylamino group 10 arylamino group; C7-11 aralkylamino group such as benzylamino group and phenylethylamino group; formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group, etc. C1-7 acylamino group; C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; carbamoyl group; dimethyl Substituted carbamoyl groups such as rubamoyl group, phenylcarbamoyl group, N-phenyl-N-methylcarbamoyl group; imino C1-6 alkyl such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group Group; hydroxyimino C1-6 alkyl group such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; C1 such as methoxyiminomethyl group and (1-methoxyimino) ethyl group A -6 alkoxyimino C1-6 alkyl group;

  Mercapto group; isothiocyanato group; thiocyanato group; C 1-6 alkylthio such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; thiazolylthio groups and pyridylthio groups A heteroarylthio group of C7-11 aralkylthio group such as benzylthio group and phenethylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbonyl group, n- butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (C1-6 alkylthio such as carbonyl groups) carbonyl group;

  C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group and the like A C6-10 arylsulfinyl group such as thiazolylsulfinyl group and heteroarylsulfinyl group such as pyridylsulfinyl group; C7-11 aralkylsulfinyl group such as benzylsulfinyl group and phenethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, t- C1-6 alkylsulfonyl group such as butylsulfonyl group; C2-6 alkenylsulfonyl group such as allylsulfonyl group; C2 such as propargylsulfonyl group A C6-10 arylsulfonyl group such as a phenylsulfonyl group; a heteroarylsulfonyl group such as a thiazolylsulfonyl group or a pyridylsulfonyl group; a C7-11 aralkylsulfonyl group such as a benzylsulfonyl group or a phenethylsulfonyl group;

  5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl group, pyridinyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl And a tri-C1-6 alkylsilyl group such as a silyl group and a t-butyldimethylsilyl group; a triphenylsilyl group;

  These “substituents” may have another “substituent” therein. For example, a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.

  In addition, these “substituents” may be divalent or higher valent groups that can be substituted at two or more locations. For example, examples of the divalent substituent include a C1-8 alkylene group such as a butylene group, a pentylene group, and a hexylene group; an oxyoxalyloxy group;

  The n-valent aliphatic saturated hydrocarbon group in R is a group having a structure in which n hydrogen atoms in the aliphatic saturated hydrocarbon are removed. Examples of the aliphatic saturated hydrocarbon include methane, ethane, propane, butane, 2-methylpropane, pentane, and hexane. Preferred groups that can be a substituent in the n-valent aliphatic saturated hydrocarbon group having a substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methoxy group, an ethoxy group, an n-propoxy group, C1-C6 alkoxy groups such as i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group and t-butoxy group;

The n-valent aromatic hydrocarbon group in R is a group having a structure in which n hydrogen atoms in the aromatic hydrocarbon are removed. Examples of aromatic hydrocarbons include benzene and naphthalene.
In the n-valent aromatic hydrocarbon group having a substituent, preferred groups that can be a substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methyl group, an ethyl group, an n-propyl group, C1-6 alkyl groups such as i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; cyclopropyl group, cyclobutyl group, cyclopentyl Groups, C3-6 cycloalkyl groups such as cyclohexyl groups; methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, t-butoxy groups, etc. A C1-6 alkoxy group; a hydroxyl group; a C1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, or a trifluoromethyl group; Alkoxy groups, 2,2,2 Cl to 6 haloalkoxy group such as trifluoroethoxy; 3-chloro-5-trifluoromethyl-pyridin-2-yloxy group; and the like.

  The aliphatic hydrocarbon group substituted with an n-valent aromatic ring in R is a group having a structure in which n hydrogen atoms in the aliphatic hydrocarbon substituted with an aromatic ring are removed. Examples of the aliphatic hydrocarbon substituted with an aromatic ring include methylbenzene and ethylbenzene. Preferred groups that can be substituted in an aliphatic hydrocarbon group substituted with an n-valent aromatic ring having a substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methyl group, an ethyl group, C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group; It is done.

  The n-valent alicyclic saturated hydrocarbon group in R is a group having a structure in which n hydrogen atoms in the alicyclic saturated hydrocarbon are removed. Examples of the alicyclic saturated hydrocarbon include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane and the like. In the n-valent alicyclic saturated hydrocarbon group having a substituent, preferred groups that can serve as a substituent include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl And C1-6 alkyl groups such as a group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, and the like.

  The n-valent alicyclic unsaturated hydrocarbon group in R is a group having a structure in which n hydrogen atoms in the alicyclic unsaturated hydrocarbon group are removed. Examples of the alicyclic unsaturated hydrocarbon include cyclopentene, cyclohexene, and cyclooctene. In the n-valent alicyclic unsaturated hydrocarbon group having a substituent, preferred groups that can serve as a substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methyl group, an ethyl group, and an n- And C1-6 alkyl groups such as a propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group;

  Specific examples of the iodoalkynyl compound include 3-iodo-2-propynylcarbamic acid ester (abbreviation IPC), 3-iodo-2-propynylpropylcarbamate, 3-iodo-2-propynyl-N-butylcarbamate (abbreviation IPBC). ), 3-iodo-2-propynyl-N-hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynylphenyl carbamate, 3-iodo-2-propynyl-m-chlorophenyl carbamate, di ( 3-iodo-2-propynyl) hexyl dicarbamate and the like. Of these, IPBC is preferred. These iodoalkynyl compounds may be used singly or in combination of two or more.

  Content of the said iodoalkynyl compound is 1-90 mass% normally with respect to the whole composition, Preferably it is 5-60 mass%.

  The benzimidazole compound used in the present invention is a compound having a benzimidazole structure. Examples of the benzimidazole compound preferably used in the present invention include a compound represented by the formula (2).

式（２）中、Ｒ¹はＮＨＣＯＯＲ¹¹（Ｒ¹¹は無置換の若しくは置換基を有するＣ１〜６アルキル基を示す。）で表される基、無置換の若しくは置換基を有するフェニル基、または無置換の若しくは置換基を有する５員複素芳香環基を示す。Ｒ²は水素原子またはＣＯＮＨＲ²¹（Ｒ²¹は無置換の若しくは置換基を有するＣ１〜６アルキル基を示す。）で表される基を示す。

In formula (2), R ¹ is a group represented by NHCOOR ¹¹ (R ¹¹ represents an unsubstituted or substituted C 1-6 alkyl group), an unsubstituted or substituted phenyl group, or An unsubstituted or substituted 5-membered heteroaromatic group is shown. R ² represents a hydrogen atom or a group represented by CONHR ²¹ (R ²¹ represents an unsubstituted or substituted C 1-6 alkyl group).

Examples of the unsubstituted or substituted C1-6 alkyl group for R ¹¹ or R ²¹ include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i- Examples thereof include a butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group.
Examples of the 5-membered heteroaromatic group in R ¹¹ include pyrrolyl groups such as a pyrrol-1-yl group, a pyrrol-2-yl group, and a pyrrol-3-yl group; a furan-2-yl group and a furan-3-yl group A thienyl group such as a thiophen-2-yl group and a thiophen-3-yl group; an imidazol-1-yl group, an imidazol-2-yl group, an imidazol-4-yl group, and an imidazol-5-yl group Imidazolyl groups such as: pyrazol-1-yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazolyl-5-yl group, etc .; oxazol-2-yl group, oxazol-4-yl group Oxazolyl groups such as oxazol-5-yl group; isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group Any isoxazolyl group; thiazolyl groups such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5- Isothiazolyl groups such as yl group; 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2, Triazolyl groups such as 4-triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group; 1,2,4-oxadiazole-3 Oxadiazolyl groups such as -yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; 1,2,4-thiadiazol-3-yl group 1, , 4-thiadiazol-5-yl group, 1,3,4-thiadiazol-2-yl-thiadiazolyl group such as a group; and the like; tetrazol-1-yl group, tetrazolyl group, such as tetrazol-2-yl group.

  Specific examples of the benzimidazole compound include methyl benzimidazol-2-ylcarbamate (abbreviation BCM, generic name carbendazim), methyl 1-butylcarbamoylbenzimidazol-2-ylcarbamate (generic name benomyl), 2- (Thiazol-4-yl) benzimidazole (generic name thiabendazole), methyl 5- (propylthio) benzimidazol-2-ylcarbamate (generic name albendazole), 2- (2-chlorophenyl) benzimidazole (generic name chlorfe) Nazole), methyl 1- (5-cyanopentylcarbamoyl) benzimidazol-2-ylcarbamate (generic name cipendazole), 2- (2-ethoxyethoxy) ethylbenzimidazol-2-ylcarbamic acid (generic name devacarb), 2 (2-furyl) benzimidazole (generic name fuberidazole), 1- (2-methylthioethylcarbamoyl) benzimidazol-2-ylcarbamic acid methyl (generic name mecarbindide), 2- (3,5-dimethylpyrazol-1-yl ) Benzimidazole (generic name rabenzazole), methyl 2- (2-furylmethylene) aminophenylaminothioxomethylcarbamate (generic name furophanate), 4,4- (o-phenylene) bis (3-thioallophanate) diethyl (general Name thiophanate), 4,4- (o-phenylene) bis (3-thioallophanate) dimethyl (generic name thiophanate methyl), and the like. Of these, carbendazim is preferred. These benzimidazole compounds may be used alone or in combination of two or more.

  The isophthalonitrile compound used in the present invention is a compound having an isophthalonitrile structure. Examples of the isophthalonitrile compound preferably used in the present invention include compounds represented by the formula (3).

式（３）中、Ｘ¹〜Ｘ⁴は独立に塩素原子またはフッ素原子を示す。

In formula (3), X < ¹ > -X < ⁴ > shows a chlorine atom or a fluorine atom independently.

  Specific examples of the isophthalonitrile compound include 2,4,5,6-tetrachloroisophthalonitrile (generic name chlorothalonil), 2,4,5,6-tetrafluoroisophthalonitrile, 5-chloro-2, Examples include 4,6-trifluoroisophthalonitrile. Of these, chlorothalonil is preferred. These isophthalonitrile compounds may be used alone or in combination of two or more.

The content of the benzimidazole compound or isophthalonitrile compound is preferably 1 to 90% by mass, more preferably 5 to 70% by mass, based on the entire composition.
The ratio of the total mass of the benzimidazole compound or the isophthalonitrile compound to the total mass of the iodoalkynyl compound contained in the composition of the present invention is preferably 1/100 to 100/1, more preferably 1. / 10 to 10/1, more preferably 1/4 to 2/1.
The particle size of the benzimidazole compound or isophthalonitrile compound is not particularly limited, but is preferably 0.1 to 200 μm, more preferably 1 to 50 μm in the raw material state. The particle size is a volume-based particle size distribution obtained by measuring a benzimidazole compound or an isophthalonitrile compound with a laser diffraction scattering particle size distribution analyzer (model: LS 13 320) manufactured by Beckman Coulter. Is the value of the average particle diameter.

  A powdery fungicide composition according to another embodiment of the present invention is at least one selected from the group consisting of iodoalkynyl compounds represented by formula (1), and a pest control property having a melting point of 200 ° C. or higher. It contains at least one selected from the group consisting of substances and does not contain a water-insoluble inorganic carrier.

  In the present embodiment, the content of the iodoalkynyl compound represented by the formula (1) is usually 1 to 90% by mass, preferably 5 to 60% by mass with respect to the entire composition, as in the above-described embodiment. It is.

  The pest control substance used in the present invention is a substance having the ability to kill pests, the ability to suppress the survival or reproduction of pests, or the ability to repel pests. For example, an antiseptic, a fungicide, an algae, an ant, or an insecticide can be used.

  The pest control material used in the present invention has a melting point of 200 ° C. or higher, preferably 250 ° C. or higher. When the melting point is in the above range, blocking during storage can be suppressed.

  Pesticides having a melting point of 200 ° C. or higher include benzimidazole compounds such as carbendazim, thiabendazole, and fuberidazole; isophthalonitrile compounds such as chlorothalonil; pyrithione compounds such as copper pyrithione; decalinium chloride and hexabromide bromide Quaternary ammonium salt compounds such as decyltrimethylammonium; metals such as copper, zinc and silver, salts or compounds containing the same, and the like. These pest control substances may be used alone or in combination of two or more. Of these, carbendazim and chlorothalonil are particularly preferred.

The content of the pesticidal substance having a melting point of 200 ° C. or higher is preferably 1 to 90% by mass, more preferably 5 to 70% by mass with respect to the entire composition.
The ratio of the total mass of the pest control substance having a melting point of 200 ° C. or higher to the total mass of the iodoalkynyl compound contained in the composition of the present invention is preferably 1/100 to 100/1, more preferably. Is 1/10 to 10/1, more preferably 1/4 to 2/1.

  The particle size of the pest control substance having a melting point of 200 ° C. or higher is not particularly limited, but is preferably 0.1 to 200 μm, more preferably 1 to 50 μm in the raw material state.

The composition of the present invention does not contain a water-insoluble inorganic carrier. Here, “water-insoluble” means that the solubility in water at 20 ° C. is 0.01% by mass or less.
Examples of water-insoluble inorganic carriers include talc, kaolinite, diatomaceous earth, clay, bentonite, zeolite, sepiolite, attapulgite, vermiculite, perlite, sericite, silica, carborundum, calcium carbonate, apatite, zinc oxide, aluminum oxide, Examples include titanium dioxide.

  The powdery fungicide composition of the present invention may contain a solid carrier other than the water-insoluble inorganic carrier, a surfactant and the like.

Solid carriers other than the water-insoluble inorganic carrier are not particularly limited, but water-insoluble organic polymer carriers such as water-insoluble organic polymers such as cellulose and nitrocellulose, gel-like particles composed of polysaccharides such as agarose and starch, And potassium chloride, sodium chloride, potassium sulfate, sodium sulfate, ammonium sulfate, ammonium hydrochloride, dipotassium hydrogen phosphate, sodium carbonate, sodium hydrogen carbonate, glucose, fructose, sucrose, lactose, urea, water-soluble starch, dextrin, carboxymethylcellulose And water-soluble carriers such as polyethylene glycol, polyvinyl alcohol, and polyvinylpyrrolidone. Solid carriers other than these water-insoluble inorganic carriers can be used alone or in combination of two or more.
The content of the solid carrier other than the water-insoluble inorganic carrier contained in the composition of the present invention is preferably 0 to 95% by mass, more preferably 0 to 90% by mass, and further preferably 0 to 0% by mass with respect to the entire composition. 50% by mass.

Although it does not specifically limit as said surfactant, Nonionic surfactant, anionic surfactant, cationic surfactant, amphoteric surfactant is mentioned.
Examples of nonionic surfactants include polyoxyalkylene alkyl phenyl ether, polyoxyalkylene aryl phenyl ether, polyoxyalkylene alkyl ether, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, and polyoxyalkylene vegetable oil.

  Examples of the anionic surfactant include alkylbenzene sulfonate, alkyl naphthalene sulfonate, lignin sulfonate, naphthalene sulfonate formaldehyde condensate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate. And dialkylsulfosuccinate.

Examples of the cationic surfactant include aliphatic amine salts and quaternary ammonium salts.
Examples of amphoteric surfactants include alkyl betaine surfactants, amidopropyl betaine surfactants, imidazolinium betaine surfactants, sulfobetaine surfactants, and phosphobetaine surfactants. Can be mentioned.
These surfactants can be used alone or in combination of two or more. The content of the surfactant contained in the composition of the present invention is preferably 0 to 30% by mass, more preferably 1 to 10% by mass with respect to the entire composition.

  When other additives such as a solid carrier other than a water-insoluble inorganic carrier and a surfactant are added in a powder state, the particle size is not particularly limited, but is preferably 0.1 to 200 μm in the raw material state. Preferably it is 1-50 micrometers. The particle size is the value of the average particle size in the volume-based particle size distribution obtained by measuring other additives with a laser diffraction scattering particle size distribution analyzer (model: LS 13 320) manufactured by Beckman Coulter. It is.

  When other additives such as a solid carrier other than a water-insoluble inorganic carrier and a surfactant are added in a liquid state, a powder of iodoalkynyl compound and the benzimidazole compound or isophthalonitrile compound or a melting point of 200 ° C. It can also be set as the film | membrane which coat | covers the surface of the powder of the above pesticidal substances.

The composition of the present invention may contain a pest control substance having a melting point of less than 200 ° C. within a range not impairing the effects of the present invention.
Pesticides having a melting point of less than 200 ° C. include pyridine compounds such as 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine (TCMSP); zinc pyrithione, sodium pyrithione; imazalyl, tebuconazole, Azole compounds such as hexaconazole and epoxiconazole; 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-n-octyl-4-isothiazoline Isothiazoline compounds such as -3-one and 1,2-benzisothiazolin-3-one; thiocyanate compounds such as 2- (4-thiocyanomethylthio) benzothiazole and methylenebisthiocyanate; 2,2-dibromo-2- Nitroethanol (DBNE), 2-bromo-2-nitropropa Nitroalcohol compounds such as -1,3-diol (BNPD); guanidine compounds such as dodecylguanidine hydrochloride, dodecylguanidine acetate, iminotadine acetate, iminoctazinealbesylate; cetylpyridium chloride, benzalkonium chloride Quaternary ammonium salt compounds such as benzethonium chloride and didecyldimethylammonium chloride; phenylurea compounds such as 3- (3,4-dichlorophenyl) -1,1-dimethylurea (DCMU); 2-methylthio-4-t -Triazine compounds such as butylamino-6-cyclopropylamino-S-triazine; pyrethroid compounds such as cyfluthrin, cypermethrin, deltamethrin, phenpropatoline, bifenthrin; nedacloprid, acetamiprid, etc. Nicotinoid-based compounds; and the like.
The content of the pesticidal substance having a melting point of less than 200 ° C. is preferably 0 to 50% by mass, more preferably 0 to 20% by mass with respect to the entire composition.

  The powdery fungicide composition of the present invention is not particularly limited by the particle size. For example, it can be 0.1 to 200 μm. The particle size is a value obtained by measuring the composition with a laser diffraction scattering method particle size distribution analyzer (model: LS 13 320) manufactured by Beckman Coulter.

The powdery fungicide composition of the present invention is not particularly limited by its production method. For example, powder of the iodoalkynyl compound, powder of the benzimidazole compound or isophthalonitrile compound or a pest control substance having a melting point of 200 ° C. or higher, and solids other than the water-insoluble inorganic carrier as necessary. By mixing powder such as carrier and surfactant; powder of the iodoalkynyl compound and powder of the benzimidazole compound or isophthalonitrile compound or a pest control substance having a melting point of 200 ° C. or higher And a solution of a solid carrier other than the water-insoluble inorganic carrier or a surfactant as required, can be obtained.
Mixing can be performed by a dry mixing method or a wet mixing method.
The dry mixing method is not particularly limited. For example, it can be performed using a mixing apparatus such as a Henschel mixer, a high speed mixer, a Nauter mixer, a ribbon blender, or a power mill.
The method of wet mixing is not particularly limited. For example, an apparatus such as a ball mill, a homogenizer, a vibration mill, or a bead mill can be used.
After mixing, it can be granulated. Examples of the granulation method include spray granulation method and rolling granulation method.

The method for preventing blocking of a powder containing an iodoalkynyl compound according to an embodiment of the present invention includes at least one selected from the group consisting of a benzimidazole compound and an isophthalonitrile compound from the group consisting of the iodoalkynyl compound. Adding to at least one selected.
According to another embodiment of the present invention, there is provided a method for preventing blocking of a powder containing an iodoalkynyl compound, wherein at least one selected from the group consisting of pesticidal substances having a melting point of 200 ° C. or higher is used. Adding to at least one selected from the group consisting of compounds.
The method of addition is not particularly limited. For example, the method similar to the manufacturing method of the said powdery antifungal agent composition is mentioned.

The mechanism by which blocking of the powder containing an iodoalkynyl compound is prevented is not clear, but is presumed as follows. The melting point of iodoalkynyl compounds decreases with the addition of other substances. For example, pure IPBC has a melting point of about 66 ° C., but when mixed with other materials, the mixture may begin to melt below 54 ° C. However, when at least one selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds or at least one selected from the group consisting of pesticides having a melting point of 200 ° C. or higher is added, the melting point of the iodoalkynyl compound It seems that the decrease in the temperature is suppressed, and the powder containing the iodoalkynyl compound melts during storage and is suppressed from being fused to each other.
In the blocking prevention method according to the present invention, a water-insoluble inorganic carrier may be added as long as the effects of the present invention are not impaired.

  The powdery fungicide composition according to the present invention can be formulated into powders, granules, pellets and the like by mixing, pulverizing, granulating and the like as described above. And by adding the powdery fungicide composition according to the present invention to industrial water, metal processing oils, various industrial products, etc., microorganisms such as bacteria, molds, yeasts, algae and the like can suppress and control the growth. It is possible to prevent adverse effects such as a decrease in productivity, a decrease in quality, and the generation of malodors.

  Hereinafter, the present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

The melting points of the substances used in the examples or comparative examples are as follows.
IPBC: 65.8-66.5 ° C;
Carbendazim: 302-307 ° C .; average particle size 14.61 μm
Chlorothalonil: 252.1 ° C .; average particle size 17.26 μm
Hexaconazole: 110-112 ° C .; average particle size 35.39 μm
Tebuconazole: 105 ° C .; average particle size 37.62 μm
DCMU: 158-159 ° C .; average particle size 8.962 μm
Sibutrin: 128-133 ° C .; average particle size 12.78 μm
Bronopol: 130 ° C .;
TCMSP: 152 ° C .; average particle size 46.85 μm

[Evaluation of blocking properties]
1) Compression test The powdery fungicide composition was put in a polyethylene bag and compressed by hand, and the blocking property was evaluated according to whether it became a lump by the following index.
○: Not a lump ×: A lump.

2) High-temperature storage test 4 g of the powdery fungicide composition was put into a vial with a capacity of 20 ml and an inner diameter of 14.5 mm and capped. This was left still at 54 ° C. for 14 days. Thereafter, the lid was removed, and the mouth of the vial was faced down and held in that state for 10 seconds. The liquidity was evaluated using the following indicators.
○: The amount of the powdery fungicide composition discharged from the bottle mouth was 2 g or more.
X: The amount of the powdery fungicide composition discharged from the bottle mouth was less than 2 g.
#: A partially viscous liquid was formed by melting.

Example 1
15 parts by mass of IPBC and 15 parts by mass of carbendazim were mixed and pulverized with a wonder blender (manufactured by Osaka Chemical Co., Ltd.) for 30 seconds to obtain a powdery fungicide composition having an average particle size of μm. The results of the compression test are shown in Table 1.

(Example 2)
15 parts by weight of IPBC, 15 parts by weight of carbendazim, and 1 part by weight of sodium alkylnaphthalene sulfonate were mixed, and pulverized with a wonder blender (manufactured by Osaka Chemical Co., Ltd.) for 30 seconds. Obtained. The results of the compression test are shown in Table 1.

(Examples 3-4, Comparative Examples 1-2)
A powdery fungicide composition having an average particle size of μm was obtained in the same manner as in Example 1 except that the blending amounts of IPBC, carbendazim, and sodium alkylnaphthalenesulfonate were changed to the formulation shown in Table 1. The results of the compression test are shown in Table 1.

(Example 5)
15 parts by mass of IPBC and 15 parts by mass of carbendazim were mixed and pulverized with a wonder blender (manufactured by Osaka Chemical Co., Ltd.) for 60 seconds to obtain a powdery fungicide composition having an average particle size of μm. Table 2 shows the results of the compression test and the high temperature storage test.

(Examples 6-7 and Comparative Examples 3-10)
A powdery fungicide composition having an average particle size of μm was obtained in the same manner as in Example 5 except that the formulations shown in Table 2 and Table 3 were changed. Tables 2 and 3 show the results of the compression test and the high temperature storage test.

  As shown in the table, when a pest control substance having a melting point of less than 200 ° C. is added to IPBC, melting occurs at 54 ° C. or less, or blocking occurs. On the other hand, according to the present invention, when a pest control substance having a melting point of 200 ° C. or higher such as carbendazim or chlorothalonil, a benzimidazole compound or an isophthalonitrile compound is added to an iodoalkynyl compound such as IPBC, blocking or Melting at 54 ° C. or lower can be prevented. It can be seen that the powdery fungicide composition of the present invention can be stored stably for a long period of time even at high temperatures.

Claims (9)

Formula (1)

(In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. N-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number N represents an n-valent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is methylene in parentheses. I represents the number of groups and is an integer of 1 to 3. n represents the number of groups in parentheses bonded to R and is an integer of 1 to 3). At least one selected from the group consisting of compounds;
A powdery fungicide composition containing at least one selected from the group consisting of a benzimidazole compound and an isophthalonitrile compound and containing no water-insoluble inorganic carrier. Formula (1)

(In formula (1), a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted n-valent carbon group having 6 to 20 carbon atoms. An aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon group having 3 to 10 carbon atoms N-valent alicyclic saturated hydrocarbon group or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is the number of methylene groups in parentheses. And is an integer of any one of 1 to 3. n represents the number of groups in parentheses bonded to R, and is an integer of any of 1 to 3). At least one selected from a group;
A powdery fungicide composition containing at least one selected from the group consisting of pest control substances having a melting point of 200 ° C. or higher and containing no water-insoluble inorganic carrier.   The powdery fungicide composition according to claim 1 or 2, wherein the iodoalkynyl compound is 3-iodo-2-propynyl-N-butylcarbamate.   The powdery fungicide composition according to claim 1, wherein the benzimidazole compound is methyl benzimidazol-2-ylcarbamate.   The powdery fungicide composition according to claim 1, wherein the isophthalonitrile compound is 2,4,5,6-tetrachloroisophthalonitrile. At least one selected from the group consisting of a benzimidazole compound and an isophthalonitrile compound,
Formula (1)

(In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. N-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number N represents an n-valent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is methylene in parentheses. I represents the number of groups and is an integer of 1 to 3. n represents the number of groups in parentheses bonded to R and is an integer of 1 to 3). Adding to at least one selected from the group consisting of compounds,
A method for preventing blocking of a powder containing an iodoalkynyl compound. At least one selected from the group consisting of pest control substances having a melting point of 200 ° C. or higher,
Formula (1)

(In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. N-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number N represents an n-valent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is methylene in parentheses. I represents the number of groups and is an integer of 1 to 3. n represents the number of groups in parentheses bonded to R and is an integer of 1 to 3). Adding to at least one selected from the group consisting of compounds,
A method for preventing blocking of a powder containing an iodoalkynyl compound. At least one selected from the group consisting of benzimidazole compounds and isophthalonitrile compounds;
Formula (1)

(In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. N-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number N represents an n-valent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is methylene in parentheses. I represents the number of groups and is an integer of 1 to 3. n represents the number of groups in parentheses bonded to R and is an integer of 1 to 3). At least one selected from the group consisting of compounds;
The manufacturing method of the powdery antifungal agent composition of Claim 1 including mixing. At least one selected from the group consisting of pest control substances having a melting point of 200 ° C. or higher;
Formula (1)

(In the formula (1), R is a hydrogen atom, an unsubstituted or substituted n-valent aliphatic saturated hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted carbon group having 6 to 20 carbon atoms. N-valent aromatic hydrocarbon group, an unsubstituted or substituted aliphatic hydrocarbon group substituted with an n-valent aromatic ring having 6 to 20 carbon atoms, an unsubstituted or substituted carbon number N represents an n-valent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, or an unsubstituted or substituted n-valent alicyclic unsaturated hydrocarbon group having 3 to 10 carbon atoms, where m is methylene in parentheses. I represents the number of groups and is an integer of 1 to 3. n represents the number of groups in parentheses bonded to R and is an integer of 1 to 3). Mixing with at least one selected from the group consisting of compounds. Method for producing a powdery antifungal composition according to.