JP3343437B2 - Disinfecting composition containing silicon-containing azole compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

An object of the present invention is to provide a combined fungicide for agricultural and horticultural use which has a broad antibacterial spectrum, has a synergistic effect and prevents the development of resistant bacteria.

[0002]

The present invention relates to a novel germicidal composition for agricultural and horticultural use having an excellent bactericidal effect, comprising a combination of a silicon-containing azole compound and an ergosterol biosynthesis inhibitor.

[0003]

2. Description of the Related Art Compound (I) used as an active ingredient of the present invention is described in Japanese Patent Application No. 4-267234.

[0004] These compounds have a therapeutic and preventive effect on many plant diseases, and when used as a spray or water application agent, they can potently control sheath blight and blast, which are important diseases of rice cultivation. Can be controlled. In addition, by using as a soil treatment or seed treatment agent, Rhizoc
In addition to controlling the damping-off disease of various crops such as beet, cotton, wheat, cucumber, and legumes caused by tonia fungus, soil such as white silk disease such as eggplant and cucurbit, black bruise of potato, and eye spot disease of wheat Infectious diseases can be effectively controlled.

Another compound group (II) used as an active ingredient of the present invention is (1RS, 2RS; 1RS, 2SR) -1- (4-chlorophenoxy) -3,3-dimethyl-1- ( 1H-1,
2,4-Triazol-1-yl) butan-2-ol (hereinafter referred to as "triadimenol") 1- [2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2- Ilmethyl] -1H-
1,2,4-triazole (hereinafter referred to as “propiconazole”) (RS) -2- (2,4-dichlorophenyl) -1-
(1H-1,2,4-triazol-1-yl) hexane-2-ol bis (4-fluorophenyl) (methyl) (1H-1,
2,4-triazol-1-ylmethyl) silane (E) -4-chloro-α, α, α-trifluoro-N-
(1-Imidazol-1-yl-2-propoxyethylidene) -O-toluidine (hereinafter "triflumizole")
N-propyl-N- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1-carboxamide (hereinafter referred to as "prochloraz") cis-4- [3- (4-tert-butyl) Phenyl) -2-
Methylpropyl] -2,6-dimethylmorpholine (hereinafter referred to as “fenpropimorph”) (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H -1,
2,4-triazol-1-ylmethyl) cyclopentanol 2,2-dimethyl-4-chloro-5- (4-chlorobenzylidene) -1-cyclopentanone (2RS, 3RS; 2RS, 3SR) -2- ( 4-chlorophenyl) -3-cyclopropyl-1- (1H-1,
2,4-triazol-1-yl) butan-2-ol 4-chlorobenzyl-N-2,4-dichlorophenyl-
2- (1H-1,2,4-triazol-1-yl) thioacetamidoate 2-p-chlorophenyl-2- (1H-1,2,4-triazol-1-ylmethyl) hexanenitrile pent-4- Enyl-N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate (hereinafter, referred to as "pefurazoate") 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime (hereinafter, referred to as "pefurazoate") (Referred to as "pyrifenox") (RS) -1-p-chlorophenyl-4,4-dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol 1- (4- Chlorophenoxy) -3,3-dimethyl-1
-(1H-1,2,4-triazol-1-yl) butanone 2,6-dimethyl-4-tridecylmorpholine (hereinafter, referred to as
(Hereinafter, these compounds of group (II) are collectively referred to as “ergosterol biosynthesis inhibitors”). These compounds are used as agricultural and horticultural fungicides having an activity of inhibiting fungal ergosterol biosynthesis. It is known and has been used as a spraying agent, a seed treatment agent or a soil treatment agent for controlling various diseases such as vegetables, fruit trees, and cereals. These agents have an excellent property that they have a broad antibacterial spectrum and do not show harm to various crops at practical use concentrations.

[0006]

However, compound (I) and ergosterol biosynthesis inhibitor (II)
When applied in an excessively large amount, there is a possibility that chemical damage such as growth inhibition may occur. In addition, when ergosterol biosynthesis inhibitor (II) is used repeatedly for a long period of time, pathogens with reduced sensitivity to these drugs may appear, for example, wheat and vegetable noodles which have been effective so far. It has become difficult to control rice scab and rice blight seedling disease.

The present inventors have found that the combination preparation of the present invention exerts an unexpectedly potentiating effect on various diseases, and that the combination preparation of the present invention has a synergistic effect. Thus, the present invention has been completed.

[0008]

Configuration of the Invention

[0009]

The present invention provides a compound represented by the general formula (I):

[0010]

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Wherein A represents a 1,2,4-triazol-1-yl group or an imidazol-1-yl group;
Represents 1, 2 or 3 (when n is 2 or 3, each X may be different); X represents a hydrogen atom, a halogen atom, a phenyl group, 1 to 3 identical or different It represents a lower alkyl group optionally substituted with halogen or a lower alkoxy group optionally substituted with 1 to 3 identical or different halogens. And at least one selected from the group consisting of the following ergosterol biosynthesis inhibitors (II):
A fungicidal composition characterized by containing at least one species as an active ingredient.

[Biosynthesis inhibitor group (II)] (1RS, 2RS; 1RS, 2SR) -1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,
2,4-Triazol-1-yl) butan-2-ol 1- [2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-ylmethyl] -1H-
1,2,4-triazole (RS) -2- (2,4-dichlorophenyl) -1-
(1H-1,2,4-triazol-1-yl) hexane-2-ol bis (4-fluorophenyl) (methyl) (1H-1,
2,4-triazol-1-ylmethyl) silane (E) -4-chloro-α, α, α-trifluoro-N-
(1-Imidazol-1-yl-2-propoxyethylidene) -O-toluidine N-propyl-N- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1-carboxamide cis-4- [ 3- (4-tert-butylphenyl) -2-
Methylpropyl] -2,6-dimethylmorpholine (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,
2,4-triazol-1-ylmethyl) cyclopentanol 2,2-dimethyl-4-chloro-5- (4-chlorobenzylidene) -1-cyclopentanone (2RS, 3RS; 2RS, 3SR) -2- ( 4-chlorophenyl) -3-cyclopropyl-1- (1H-1,
2,4-triazol-1-yl) butan-2-ol 4-chlorobenzyl-N-2,4-dichlorophenyl-
2- (1H-1,2,4-triazol-1-yl) thioacetamidoate 2-p-chlorophenyl-2- (1H-1,2,4-triazol-1-ylmethyl) hexanenitrile pent-4- Enyl-N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime (RS) -1-p-chlorophenyl-4 , 4-Dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol 1- (4-chlorophenoxy) -3,3-dimethyl-1
-(1H-1,2,4-triazol-1-yl) butanone 2,6-dimethyl-4-tridecylmorpholine In the above formula (I), the "halogen atom" in X represents a fluorine atom, a chlorine atom, It represents a bromine atom or an iodine atom, and is preferably a fluorine atom or a chlorine atom.

In the above formula (I), the "lower alkyl group" for X is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, iso-pentyl , 2-methylbutyl, neopentyl, 1-
Ethylpropyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl,
3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
1 carbon atoms such as 2,3-dimethylbutyl and 2-ethylbutyl
A straight-chain or branched alkyl group having 1 to 6 carbon atoms, preferably a straight-chain or branched alkyl group having 1 to 4 carbon atoms,
More preferably, it is a methyl or ethyl group.

In the above formula (I), the “lower alkyl group optionally substituted with 1 to 3 identical or different halogens” in X includes, in addition to the unsubstituted “lower alkyl group”, Trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, 2,2,2-trichloroethyl, 2,2,2-
The above-mentioned "lower alkyl group" such as trifluoroethyl, 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl, 2,2-dibromoethyl, chloropropyl, trifluoropropyl, fluorobutyl, trichloropentyl, and trifluorohexyl; Is a group substituted by the same or different 1 to 3 halogen atoms. At this time, the lower alkyl group substituted with the same or different 1 to 3 halogens is preferably a linear or branched alkyl group having 1 to 3 carbon atoms in which the same halogen atom has 1 to 3 halogen atoms. It is a substituted group, more preferably a methyl or ethyl group substituted with 1 to 3 fluorine atoms or chlorine atoms, and most preferably a trifluoromethyl group.

In the above formula (I), the "lower alkoxy group" in X is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentoxy, Isopentoxy,
2-methylbutoxy, neopentoxy, 1-ethylpropoxy, n-hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy, 1-methylpentoxy, 3,3-dimethylbutoxy, 2, 2-dimethylbutoxy, 1,
A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as 1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy It is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy or ethoxy group.

In the above formula (I), the “lower alkoxy group optionally substituted with 1 to 3 identical or different halogens” in X includes, in addition to the unsubstituted “lower alkoxy group”, Trifluoromethoxy, trichloromethoxy, difluoromethoxy, dichloromethoxy,
Dibromomethoxy, fluoromethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, 2-bromoethoxy, 2-chloroethoxy, 2-fluoroethoxy, 2,2-
Dibromoethoxy, chloropropoxy, trifluoropropoxy, fluorobutoxy, trichloropentoxy,
The above-mentioned "lower alkoxy group" such as trifluorohexyloxy is a group in which the same or different 1 to 3 halogen atoms are substituted. At this time, as the lower alkoxy group substituted with the same or different 1 to 3 halogens, preferably, the same halogen atom as the 1 to 3 carbon atoms in the straight or branched chain alkoxy group has 1 to 3 halogen atoms. It is a substituted group, more preferably a methoxy or ethoxy group substituted with 1 to 3 fluorine atoms or chlorine atoms, and most preferably a trifluoromethoxy group.

In the general formula (I), A is preferably a 1,2,4-triazol-1-yl group.

In the above general formula (I), n is preferably 1 or 2, more preferably 1.

In the above formula (I), X is preferably a hydrogen atom or a halogen atom, more preferably a fluorine atom or a chlorine atom.

In the above general formula (I), the substitution position of X is preferably 2-position, 4-position, or 2,
It is the fourth position, more preferably the fourth position.

Examples of the silicon-containing azole derivative represented by the general formula (I) used in the present invention are shown in Table 1, but the compound (I) of the present invention is not limited thereto.

[0022]

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[0023]

[Table 1] {Compound No. A (X) _n} ───────────────────────────────── 1 1,2,4-triazol-1-yl H 2 1,2 , 4-Triazol-1-yl 4-Cl 3 1,2,4-triazol-1-yl 4-F 4 1,2,4-triazol-1-yl 4-Br 5 1,2,4-triazol- 1-yl 4-CH ₃ 1,2,4-triazol-1-yl 4-CF ₃ 1,2,4-triazol-1-yl 4-OCH ₃ 8 1,2,4-triazol-1-yl Yl 4-Ph 9 1,2,4-triazol-1-yl 4-OCF ₃ 10 1,2,4-triazol-1-yl 4-CH ₂ CH ₃ 11 1,2,4-triazol-1-yl 2,4-Cl ₂ 12 1,2,4- Toriaso Bu Lumpur-1-yl 2,4-F ₂ 13 1,2,4- Toriaso Bu Lumpur-1-yl 2-C , 4-F 14 1,2,4- Toriaso Bu Lumpur-1-yl 2-F, 4-Cl 15 1,2,4- Toriaso Bu Lumpur-1-yl 2-OCH ₃ 16 1,2,4- Toriaso Bu Lumpur -1- Yl 2-Cl 17 1,2,4-triazol-1-yl 2-F 18 1,2,4-triazol-1-yl 2,6-Cl ₂ 19 1,2,4-triazol-1-yl 2 , 6-F ₂ 20 1,2,4-Triazol-1-yl 2-Cl, 6-F 21 1,2,4-Triazol-1-yl 3-OCH ₃ 22 1,2,4-Triazol-1 -Yl 3-Cl 23 1,2,4-triazol-1-yl 2,4,6-Cl ₃ 24 1,2,4-triazol-1-yl 2,4,6-Me ₃ 25 1,2, 4-triazol-1-yl 4-CH (CH ₃ ) ₂ 26 1,2,4-triazol-1-yl 4-CH ₂ CH ₂ CH ₃ 27 1,2,4-triazol-1-yl 4-CH _{2 CH 2 CH 2 CH 3 28} 1,2,4- Toriaso Bu Lumpur-1-yl 4 OCF ₂ CF ₃ 29 1,2,4- Toriaso Bu Lumpur-1-yl 3,4-Cl ₂ 30 1,2,4- Toriaso Bu Lumpur-1-yl 3,4-F ₂ 31 1,2,4- Toriaso Bu Lumpur -1 -Yl 3,4-Br ₂ 32 1,2,4-triazol-1-yl 4-CH ₂ F 33 1,2,4-triazol-1-yl 4-CHF ₂ 34 1,2,4-triazol- 1-yl 4-OCH ₂ F 35 1,2,4-triazol-1-yl 4-OCHF ₂ 36 1,2,4-triazol-1-yl 4-OCF ₂ Br 37 1,2,4-triazol- 1-yl 4-CF ₂ Cl 38 1,2,4-triazol-1-yl 3,5-Cl ₂ -4-OCF ₃ 39 imidazol-1-yl H 40 imidazol-1-yl 4-Cl 41 imidazol-yl 1- yl 4-F 42 Imita Bu Seo Bu Lumpur-1-yl 4-Br 43 Imita Bu Seo Bu Lumpur-1-yl 4-CH ₃ 44 Imita Bu Seo Bu Lumpur-1-yl 4 F ₃ 45 Imita Bu Seo Bu Lumpur-1-yl 4-OCH ₃ 46 Imita Bu Seo Bu Lumpur-1-yl 4-Ph 47 Imita Bu Seo Bu Lumpur-1-yl 4-OCF ₃ 48 Imita Bu Seo Bu Lumpur-1-yl 4-CH ₂ CH ₃ 49 Imita Bu Seo Bu Lumpur-yl 2 , 4-Cl ₂ 50 imidazol-1-yl 2,4-F ₂ 51 imidazol-1-yl 2-Cl, 4-F 52 imidazol-1-yl 2-F, 4-Cl 53 imidazol-1-yl 2 —OCH ₃ 54 imitasol-1-yl 2-Cl 55 imitasol-1-yl 2-F 56 imitasol-1-yl 2,6-Cl ₂ 57 imitasol-1-yl 2,6-F ₂ 58 imitasol-1-yl yl 2-Cl, 6-F 59 Imita Bu Seo Bu Lumpur-1-yl 3-OCH ₃ 60 Imita Bu Seo Bu Lumpur-1-yl 3-Cl ─────────────の う ち Of the above exemplified compounds, preferably 1, 2, 3, 4,
5, 6, 9, 11, 12, 13, 14, 15, 16, 1
Compounds Nos. 7, 18, and 19, more preferably 1,
Compounds Nos. 2, 3, 6, 11, 12, 13, and 14, most preferably compounds Nos. 2, 3, and 12.

The compound (I) of the present invention can be produced by the production method shown in the following scheme.

[0025]

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[In the above scheme, A, X and n
Is as defined above, and M is a lithium atom or MgZ
(Z represents a chlorine atom or a bromine atom), and Y represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Hereinafter, each step will be described in more detail.

(Method A) In step A, ketone (VII) is
In this step, the compound (I) of the present invention is produced by adding the silyl compound (III).

Ketone (VII) is disclosed in JP-B-63-460.
It can be produced according to the method described in JP-A-75-75.

The silyl compound (III) can be obtained from halomethyltrimethylsilyl and metallic magnesium or metallic lithium by a conventional method.

This step is performed in the presence of a solvent.

The amount of the organometallic compound represented by the formula (III) used in this step is preferably 1 to 10 equivalents, more preferably 1 to 2 equivalents to the compound of the formula (VII). It is.

The solvent used is not particularly limited as long as it does not inhibit the reaction, but is preferably a hydrocarbon such as hexane, cyclohexane, benzene or toluene, dichloromethane, chloroform, dichloroethane, or the like.
Halogenated hydrocarbons such as tetrachloroethane, dioxane, diethyl ether, tetrahydrofuran (TH
F), ethers such as ethylene glycol dimethyl ether, dimethylformamide, dimethylacetamide,
An amide such as hexamethylphosphoric triamide (HMPA) or a mixed solvent thereof, and more preferably an ether.

The reaction temperature is usually -20 ° C to 80 ° C, preferably 10 ° C to 40 ° C.

The reaction time depends mainly on the reaction temperature, the starting compound and the type of solvent used, but is usually from 5 minutes to 24 hours, preferably from 3 hours to 10 hours.

(Method B) In the step B-1, the ketone (IV)
Is a step of producing a compound (V) by adding a silyl compound (III) to the compound (III).

Step B-2 is a step of reacting compound (V) with an excess of 1,2,4-triazole or imidazole in the presence of a base to obtain compound (I) of the present invention via epoxide (VI). It is.

The reaction is carried out by reacting one or more equivalents of 1,2,4-triazole or imidazole with respect to the compound of the formula (V) in a solvent in the presence of one or more equivalents of a base, or , 2,4-triazole or imidazole.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. Preferably, the solvent is an aliphatic hydrocarbon such as hexane, heptane, ligroin or petroleum ether. Hydrogens; aromatic hydrocarbons such as benzene, toluene, xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane , Dimethoxyethane, ethers such as diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, isoamyl alcohol, diethylene glycol, glycerin Octanol, cyclohexanol, methyl cellosolve, alcohols such as;
Nitro compounds such as nitroethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; formamide, dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide, 1,
Amides such as 3-dimethyl-2-imidazolidinone; sulfoxides such as dimethylsulfoxide and sulfolane; more preferably, formamide, dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide, and 1,3- Amides such as dimethyl-2-imidazolidinone.

The base to be used is not particularly limited as long as it is used as a base in a usual reaction, but is preferably an alkali metal carbonate such as sodium carbonate or potassium carbonate; sodium hydrogen carbonate, carbonate Alkali metal bicarbonates such as potassium hydrogen; alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride; sodium hydroxide, potassium hydroxide;
Alkali metal hydroxides such as barium hydroxide; sodium methoxide, sodium ethoxide, potassium-t
-Alkali metal alkoxides such as butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-
Dimethylamino) pyridine, N, N-dimethylaniline, N,
N-diethylaniline, 1,5-diazabicyclo [4.3.0] nona
-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABC
O), 1,8-diazabicyclo [5.4.0] undec-7-ene (DB
Organic bases such as U) or organometallic bases such as butyllithium and lithium diisopropylamide;
More preferably, it is an alkali metal carbonate such as sodium carbonate or potassium carbonate.

In order to carry out the reaction effectively, quaternary ammonium salts such as benzyltriethylammonium chloride and tetrabutylammonium chloride,
Alkaline earth metal halides such as sodium iodide, sodium bromide and lithium bromide, and crown ethers such as dibenzo-18-crown-6- can also be added.

The reaction is carried out at a temperature of -78 ° C to 200 ° C, preferably -20 ° C to 150 ° C.

The reaction time varies depending mainly on the reaction temperature, the starting compound and the kind of the solvent used, but is usually 1 hour to 24 hours, preferably 2 to 10 hours.

The ketone (IV) can be obtained from Beilsteins Handbuc
h, Organischen Chemie, 7 , 285, 7 , 283.

The mixing ratio of the compound (I), which is an active ingredient of the composition of the present invention, to the ergosterol biosynthesis inhibitor (II) can be varied within a relatively wide range, but the azole derivative (I) is usually used. The ergosterol biosynthesis inhibitor (II) is used in an amount of 0.01 to 100 parts by weight, preferably 0.5 to 10 parts by weight, based on 1 part by weight.

In order to obtain the same effect as the present invention,
Compound (I) and ergosterol biosynthesis inhibitor (II) for surface application or treatment of soil or seed,
It can also be used individually and continuously within a short time.

The mixture of the present invention is used together with auxiliaries usually used in the field of pharmaceutical preparations. The active ingredients of the azole derivative (I) and the ergosterol biosynthesis inhibitor (II) can be produced in a known manner, for example, by using an emulsion stock solution, a sprayable paste,
Formulated in sprayable or dilutable solutions, emulsions, wettable powders, aqueous solvents, powders, and capsules, for example, with polymeric substances. And, for the purpose of labor saving and safety, etc., pesticide formulations (granules,
(Tablets, wettable powders, capsules, etc.) in the form of an appropriate water repellent, foaming agent, spreading agent, etc., and can be directly wrapped in water-soluble paper and thrown into water.

The above-mentioned preparations are used as they are or diluted with water or the like, and are applied to plants or water, or applied to soil.

That is, the above formulation is sprayed or dusted on a plant, sprayed, dusted or granulated on the surface of water such as a paddy field or the surface of a soil, or further mixed with the soil if necessary. Can be used.

When used as a seed treating agent,
It can be used after a seed dressing treatment, a seed dipping treatment and the like. In addition, by mixing and using other bactericides, it is expected that bactericidal efficacy is enhanced.

In addition, other fungicides, insecticides, acaricides,
It can also be used with or without admixture with nematicides, herbicides, seed disinfectants, fertilizers or soil conditioners.

The composition of the present invention can be used as an active ingredient of a fungicide for paddy fields, fields, orchards, pastures, turf, and the like.

The application rate of the composition of the present invention varies depending on the mixing ratio of active ingredients, weather conditions, formulation, application time, method, place, target disease, target crop, etc., but is usually from 0.01 g per 1 are. 1000 g, preferably 0.1 g to
100 g. When the emulsion, wettable powder, suspension, liquid preparation, etc. are diluted with water and applied, the application concentration is 0.0001.
１1%, preferably 0.001 to 0.5%, and granules, dusts and the like are applied as they are without any dilution.

At the time of seed treatment, the total amount of the active ingredients is, for example, about 0.001 to about 50 g per kg of seed,
Preferably, about 0.01 to about 10 g can be used.

In the soil treatment, usually about 0.01 g to 1000 g as the total amount of active ingredients per 1 are,
Preferably, about 0.1 g to 100 g can generally be used.

In the water surface treatment of a paddy field, the total amount of the active ingredients can be, for example, about 0.001 to about 40 kg, preferably about 0.01 to about 10 kg per hectare. For seedling box processing, one box (80 cm × 60
cm × 8 cm), the total amount of the active ingredient is about 0.1 to about 1
00 g, preferably about 0.1 to about 50 g.

When the composition of the present invention is used in rice cultivation, it can be used from the time when rice seedlings are raised in a nursery box to the time after rice transplanting and harvesting, and the effect lasts for a long time. .

[0057]

The combined fungicide of the present invention is effective against plant diseases caused by, for example, the following bacteria.

Ascomycetes; Erysiphe, Sphaerotheca, Po
dosphaera, Gibberella, Pyrenophora, Venturia, Coch
liobolus, Sclerotinia, Monilinia Basidiomycetes; Ustilago, Tilletia, Puccinia, Gymnospo
rangium, Uromyces, Corticium, Pellicularia, Typhul
a Incomplete fungi; Phoma, Ascochyta, Septoria, Phomopsis,
Colletotrichum, Pestalotia, Monilia, Verticilliu
n, Helminthosporium, Alternaria, Fusarium, Rhizoct
onia, Sclerotium, Pyricularia The combined fungicide of the present invention exerts a high synergistic effect on various airborne, soil-borne and seed-borne diseases,
It is possible to exceed the effect of using each active ingredient alone and to reduce the amount of active ingredient to be applied. As a treatment method, besides foliage application and soil treatment, a seed dressing that can be carried out with a small amount of an active ingredient is possible. In addition, in paddy fields, besides being applied to the surface of water in the form of granules, it is wrapped in water-soluble paper together with a suitable water repellent, foaming agent, spreading agent, etc. in the form of an agrochemical formulation that disperses or dissolves easily in water or on the surface of water. It has features in terms of labor saving and safety as it can be used.

[0059]

The present invention will be described in more detail with reference to the following Examples, Reference Examples and Test Examples, but the compounds, additives and their mixing ratios in the Examples are not limited thereto. The percentages used in the examples are percentages by weight unless otherwise specified.

[0060]

Example 1 (Wettable powder) 20 parts of triadimenol, 20 parts of compound 3 (indicating the compound number in Table 1, hereinafter the same), white carbon 2
0 parts, 3 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate and 35 parts of clay were mixed and sufficiently pulverized to obtain a wettable powder.

[0061]

Example 2 (Wettable powder) 20 parts of triflumizole, 10 parts of compound 2, 10 parts of white carbon, 5 parts of sodium alkylbenzenesulfonate and 55 parts of clay were mixed and pulverized to obtain a wettable powder.

[0062]

Example 3 (Wettable powder) 50 parts of tridemorph, 5 parts of compound 11, 5 parts of white carbon, 3 parts of polyoxyethylene nonylphenol ether, 2 parts of sodium naphthalenesulfonate and 35 parts of clay were mixed and sufficiently pulverized. , A wettable powder was obtained.

[0063]

Example 4 (Flowable agent) 45 parts of water, 1 part of polyoxyethylene nonylphenyl ether and 4 parts of sodium ligninsulfonate were added and stirred well, and then 20 parts of compound 3 and 20 parts of prochloraz were added. Mix and disperse uniformly using a homomixer,
Further, 10 parts of a 2% xanthan gum aqueous solution is added and stirred,
A flowable was obtained.

[0064]

Example 5 (Wettable powder) 10 parts of triazimenol, 10 parts of triflumizole,
20 parts of Compound 3, 20 parts of white carbon, 3 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate and 35 parts of clay were sufficiently mixed and pulverized to obtain a wettable powder.

[0065]

Example 6 (Wettable powder) 10 parts of triadimenol, 10 parts of prochloraz, 20 parts of compound 3, 20 parts of white carbon, 3 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate and 35 parts of clay are mixed. And pulverized sufficiently to obtain a wettable powder.

[0066]

Example 7 (Wettable powder) 10 parts of triadimenol, 20 parts of fenpropimorph,
20 parts of Compound 3, 20 parts of white carbon, 3 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate and 35 parts of clay were sufficiently mixed and pulverized to obtain a wettable powder.

[0067]

Example 8 (Wettable powder) 10 parts of triflumizole and 10 parts of triazimenol
Parts, 10 parts of compound 2, 10 parts of white carbon, 5 parts of sodium alkylbenzenesulfonate and clay 55
The parts were mixed and pulverized to obtain a wettable powder.

[0068]

[Reference example]

[0069]

REFERENCE EXAMPLE 1 2-Phenyl-1- (1H-1,2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol ether (50 ml) was poured into 2- (1H-1,2,2,2-propanol). 4-triazol-1-yl) acetophenone (0.505
g, 2.7 mmol), and the solution was stirred at room temperature under a nitrogen stream, and trimethylsilylmethylmagnesium chloride (13.5 ml of a 1 mol solution of tetrahydrofuran, 13.5 ml) was added.
Mmol) was added dropwise at a rate such that the temperature of the reaction mixture did not exceed 25 ° C. The added mixture was stirred at room temperature for 30 minutes and then heated to reflux for 6 hours, then cooled and cooled with ice water (10%).
0 ml), adjusted to pH 6 with 5% hydrochloric acid and ethyl acetate (3 ×
50 ml). The organic layers are combined and saturated saline (3 ×
(50 ml), and the organic layer was dried (Na ₂ So ₄ ) and evaporated to give a crude oil. Purification was by silica gel column chromatography (ethyl acetate: hexane = 1: 1 → 2:
1) to give the title compound. 0.112 g (15% yield) (Production method A) Melting point 86-87 ° C NMR spectrum (CDCl ₃ ) δppm: -0.20 (9H, s), 1.20 (1
H, d, J = 14.5Hz), 1.41 (1H, d, J = 14.5Hz), 4.48 (1H, d, J = 14.8
Hz), 4.58 (1H, d, J = 14.8Hz), 7.35 to 7.24 (5H, m), 7.97 (1H,
s), 8.59 (1H, s) Mass spectrum (M / Z): 276 (M ⁺ ), 260, 193

[0070]

Reference Example 2 2- (4-fluorophenyl) -1- (1H-1,2,2
4-Triazol-1-yl) -3-trimethylsilyl-2-propanol 60% sodium hydride (1.62 g, 0.04 mol) was added to dimethylformamide (60 ml), and the mixture was cooled and stirred with ice water. The lower 1,2,4-triazole (2.91 g, 0.04 mol) is added. The reaction mixture was further stirred at room temperature for 30 minutes, and then the 1-chloro-2- (4-fluorophenyl) -3- obtained in Reference Example 1 was obtained.
Trimethylsilyl-2-propanol (5.5 g, 0.
021 mol), and the mixture is heated and stirred at 90 ° C. for 30 minutes. Then cool and pour into ice water (200 ml)
The mixture was extracted with ethyl acetate (300 ml), the ethyl acetate layer was washed with saturated saline (100 ml × 3), the ethyl acetate layer was dried (Na ₂ SO ₄ ), and evaporated to give a crude oil, which was further purified by silica gel column chromatography. Chromatography (ethyl acetate: hexane = 1: 5 → 1: 1 → 2: 1) gave the title compound. 2.9 g (47% yield) (Production method B) Melting point 118-119 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.18 (9H, s), 1.16 (1
H, d, J = 14.5Hz), 1.33 (1H, d, J = 14.5Hz), 4.36 (1H, d, J = 14.0
Hz), 4.43 (1H, d, J = 14.0Hz), 6.93 to 7.01 (2H, m), 7.26 to
7.31 (2H, m), 7.91 (1H, s), 7.99 (1H, s) Mass spectrum (M / Z): 293 (M ⁺ ), 278, 211 Hereinafter, Reference Example 1 (Production Method A) and Reference Example 2 ( The following compounds were obtained in the same manner as in Production Method B).

[0071]

Reference Example 3 2- (4-chlorophenyl) -1- (1H-1,2,4
-Triazol-1-yl) -3-trimethylsilyl-
2-propanol yield 7%, melting point 108-110 ° C NMR spectrum (CDCl ₃ ) δppm: -0.19 (9H, s), 1.15 (1
(H, d, J = 14.5Hz), 1.31 (1H, d, J = 14.5Hz), 4.35 (2H, s), 7.17
-7.33 (4H, m), 7.80 (1H, s), 7.88 (1H, s) Mass spectrum (M / Z): 309 (M ⁺ ), 294,227,
211

[0072]

Reference Example 4 2- (4-bromophenyl) -1- (1H-1,2,4
-Triazol-1-yl) -3-trimethylsilyl-
2-propanol yield 11%, melting point 120-121 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.18 (9H, s), 1.20 (1
H, d, J = 14.5Hz), 1.35 (1H, d, J = 14.5Hz), 4.43 (1H, d, J = 13.9
Hz), 4.51 (1H, d, J = 13.9Hz), 7.25 (2H, d, J = 8.1Hz), 7.41
(1H, d, J = 8.1Hz), 7.96 (1H, s), 8.50 (1H, s) Mass spectrum (M / Z): 353 (M ⁺ ), 273,257

[0073]

Reference Example 5 2- (4-methylphenyl) -1- (1H-1,2,4
-Triazol-1-yl) -3-trimethylsilyl-
2-propanol yield 4%, melting point 101 ° C NMR spectrum (CDCl ₃ ) δppm: -0.19 (9H, s), 1.15 (1
H, d, J = 14.4Hz), 1.36 (1H, d, J = 14.4Hz), 2.30 (3H, s), 4.35
(1H, d, J = 14.0Hz), 4.43 (1H, d, J = 14.0Hz), 7.07 (2H, dd, J
= 8.3,1.8Hz), 7.18 (2H, dd, J = 8.3Hz), 7.90 (2H, s) mass vector (M / Z): 289 (M ⁺ ), 274,256,207

[0074]

Reference Example 6 2- (4-ethylphenyl) -1- (1H-1,2,4
-Triazol-1-yl) -3-trimethylsilyl-
2-propanol yield 4.0%, melting point 80-81 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.16 (9H, s), 1.23 (3
H, t, J = 7.6Hz), 1.74 (1H, d, J = 14.1Hz), 1.95 (1H, d, J = 14.1H
z), 2.64 (2H, q, J = 7.6Hz), 4.11 (1H, d, J = 12.1Hz), 4.38 (1
H, d, J = 12.1Hz), 7.05 (2H, dd, J = 8.5,2.0Hz), 7.90 (2H, dd, J
= 8.5,2.0Hz), 8.11 (1H, s), 8.48 (1H, s) Mass spectrum (M / Z): 303 (M ⁺ ), 272,131

[0075]

Reference Example 7 2- (4-phenylphenyl) -1- (1H-1,2,2
4-triazol-1-yl) -3-trimethylsilyl-2-propanol yield 16%, mp 97 to 100 ° C. NMR spectrum _{(CDCl 3) δppm: -0.17 (} 9H, s), 1.20 (1
H, d, J = 14.6Hz), 1.42 (1H, d, J = 14.6Hz), 4.50 (2H, s), 7.33
7.62 (9H, m), 7.96 (1H, s), 8.34 (1H, s) Mass spectrum (M / Z): 351 (M ⁺ ), 269, 179

[0076]

Reference Example 8 2- (4-trifluoromethylphenyl) -1- (1H
-1,2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol 8% yield, melting point 144 ° C. NMR spectrum (CDCl ₃ ) δ ppm: −0.19 (9H, s), 1.20 (1
H, d, J = 14.5Hz), 1.34 (1H, d, J = 14.5Hz), 4.44 (1H, d, J = 14.8
Hz), 4.45 (1H, d, J = 14.8 Hz), 7.93 (1H, s), 8.10 (1H, s) Mass spectrum (M / Z): 344 (M + 1) ⁺ , 328, 26
1,234,171

[0077]

Reference Example 9 2- (4-methoxyphenyl) -1- (1H-1,
2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol 13% yield, melting point 85-87 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.14 (9H, s), 1.72 (1
H, d, J = 14.5Hz), 1.93 (1H, d, J = 14.5Hz), 4.11 (2H, d, J = 11.9
Hz), 4.33 (2H, d, J = 11.9Hz), 6.88 (2H, dd, J = 9.0,2.2Hz),
7.08 (2H, dd, J = 9.0,2.2Hz), 8.01 (1H, s), 8.19 (1H, s) Mass spectrum (M / Z): 305 (M ⁺ ), 290,274,
133

[0078]

Reference Example 10 2- (3-Methoxyoxyphenyl) -1- (1H-1,
2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol 12% yield, melting point 91-92 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.17 (9H, s), 1.15 (1
(H, d, J = 14.4Hz), 1.25 (1H, d, J = 14.4Hz), 3.77 (3H, s), 4.39
(2H, s), 6.78 (1H, m), 6.86 (2H, m), 7.22 (1H, m), 7.84 (1H, m
s), 7.89 (1H, s) Mass spectrum (M / Z): 305 (M ⁺ ), 290, 275,
221

[0079]

Reference Example 11 2- (2-methoxyphenyl) -1- (1H-1,
2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol 12% yield, melting point 135-136 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.197 (9H, s), 1.78
(1H, d, J = 14.1Hz), 2.26 (1H, d, J = 14.1Hz), 3.60 (3H, s),
4.02 (1H, d, J = 11.7Hz), 4.56 (1H, d, J = 11.7Hz), 6.85-7.0
2 (2H, m), 7.14-7.33 (2H, m), 7.92 (1H, s), 8.25 (1H, s) Mass spectrum (M / Z): 305 (M ⁺ ), 290, 275,
221

[0080]

Reference Example 12 2- (2,4-difluorophenyl) -1- (1H-
1,2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol yield 26.5%, melting point 112-114 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.17 (9H, s), 1.23 ( 1
H, d, J = 14.5Hz), 1.48 (1H, dd, J = 14.5,2.0Hz), 4.41 (1H, d, J
= 13.7Hz), 4.43 to 4.72 (1H, br), 4.69 (1H, d, J = 13.7Hz),
6.69 to 6.79 (1H, m), 7.40 to 7.49 (1H, m), 7.83 (1H, s), 7.8
7 (1H, s) mass spectrum (M / Z): 312 (M + 1) ⁺ , 296,229

[0081]

Reference Example 13 2- (2,4-dichlorophenyl) -1- (1H-1,
2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol yield 4.1%, melting point 136-137 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.10 (9H, s), 1.36 (1
H, d, J = 14.5Hz), 2.04 (1H, d, J = 14.5Hz), 4.6 (1H, d, J = 14.0H
z), 5.38 (1H, d, J = 14.0Hz), 7.3 (1H, dd, J = 8.1,2.1Hz), 7.42
~ 7.5 (1H, m), 7.78 (1H, d, J = 8.1Hz), 7.98 (1H, s), 8.04 (1
H, s) Mass spectrum (M / Z): 344 (M ⁺ ), 326, 261,
214

[0082]

Reference Example 14 2- (2-fluoro-4-chlorophenyl) -1- (1
H-1,2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol Yield 6%, melting point 129-130 ° C. NMR spectrum (CDCl ₃ ) δ ppm: −0.164 (9H, s), 1.20 ( 1
H, d, J = 14.6Hz), 1.50 (1H, dd, J = 14.6,1.9Hz), 4.48 (1H, d, J
= 13.7Hz), 4.74 (1H, d, J = 13.8Hz), 4.51 ~ 4.77 (1H, br), 6.
99 ~ 7.05 (2H, m), 7.37 ~ 7.45 (1H, m), 7.87 (1H, s), 8.21 (1
H, s) Mass vector (M / Z): 327 (M ⁺ ), 312, 245, 155

[0083]

Reference Example 15 2- (2-chloro-4-fluorophenyl) -1- (1
H-1,2,4-triazol-1-yl) -3-trimethylsilyl-2-propanol Yield 5%, melting point 139-140 ° C NMR spectrum (CDCl ₃ ) δ ppm: -0.17 (9H, s), 1.20 ( 1
H, d, J = 14.6Hz), 2.04 (1H, d, J = 14.6Hz), 4.53 (1H, d, J = 14.0
Hz), 5.34 (1H, d, J = 14.0Hz), 6.87 (1H, ddd, J = 9.0,8.2,6.3H
z), 7.06 (1H, dd, J = 8.2,2.7Hz), 7.65 (1H, dd, J = 9.0,6.3H
z), 7.86 (1H, s), 8.23 (1H, s) Mass spectrum (M / Z): 327 (M ⁺ ), 312, 245,
155

[0084]

Reference Example 16 2- (4-fluorophenyl) -1- (1H-1,3-
Imidazol-1-yl) -3-trimethylsilyl-2
- propanol 5% yield, amorphous NMR spectrum _{(CDCl 3) δppm: -0.18 (} 9H, s), 1.21 (1
H, d, J = 16.1Hz), 1.42 (1H, d, J = 16.1Hz), 3.95 (2H, bs), 6.95
~ 7.05 (2H, m), 7.12 (2H, s), 7.25 ~ 7.35 (2H, m), 7.72 (1H, m
s) Mass spectrum (M / Z): 293 (M + 1) ⁺ , 277, 21
1,203

[0085]

Reference Example 17 1-chloro-2- (4-fluorophenyl) -3-trimethylsilyl-2-propanol 2-chloro-4'-fluoroacetophenone (8.63
g, 0.05 mol) in ether (60 ml) and trimethylsilylmethylmagnesium chloride (ether solution 200 ml, 0.057 mol) in a nitrogen stream with stirring.
Is added dropwise at such a rate that the temperature of the reaction mixture does not exceed 15 ° C. to 20 ° C., followed by stirring at room temperature for 1 hour. Ice solution 2
Then, the mixture was adjusted to pH 6 to 7 with 5% hydrochloric acid, extracted with 100 ml of ethyl acetate, and the organic layer was washed with saturated saline (50 ml).
1 × 2), and the organic layer was dried (Na ₂ SO ₄ ) and evaporated to give a crude oil. Purification was by silica gel column chromatography (ethyl acetate: n-hexane = 1: 10 → 1: 5)
Then, 8.8 g (yield 67.7%) of an oily substance of the title compound was obtained.

Elemental analysis value: C ₁₂ H ₁₈ ClFOSi; Calculated value (%) C 55.26 H 6.96 Cl 13.59 F
7.26 Analytical value (%) C 55.02 H 6.96 Cl 13.58 F
7.43 NMR spectrum: δ ppm (CDCl ₃ ) −0.18 (9H, s), 1.23 (1H, d, J = 14.7 Hz), 1.45 (1H, d, J = 14.7H)
z), 3.70 (1H, d, J = 11.0Hz), 3.80 (1H, d, J = 11.0Hz), 6.99-
7.09 (2H, m), 7.35-7.43 (2H, m)

[0087]

[Test example]

[0088]

[Test Example 1] Beet brown spot disease controlling effect Using 6-leaf beet (cultivar: Monohill), the area of one section was 5 m ^2, and the test was performed in triplicate.

Disease inoculation was carried out by cutting diseased leaves of a field where a benzimidazole drug was continuously sprayed and inoculating the entire test field on June 25. Chemical spraying is 1 from July 10
A total of three applications were made at 4 day intervals. 20 days after the last application
About 0 strains, the onset degree of beet brown spot was investigated according to the following onset index, and the onset degree was calculated by the following equation. Based on this, the control value (%) was determined from the comparison with the non-sprayed plot.

Disease index (degree of disease) 0: No lesion 1: Less than 10% of leaf area is affected 2: 10% or more to less than 40% of leaf area is affected 3: 40% or more to less than 70% of leaf area 4: Disease occurs more than 70% of leaf area

[0091]

[Equation 1] Severity (%) = ({(Severity index x number of strains))}
(4 × total number of investigated leaves) × 100 Control value (%) = {1− (degree of disease in treated area ÷ degree of disease in non-sprayed area)} × 100 Investigation of phytotoxicity was performed according to the following index. Table 2 shows the results.

Chemical damage index 0: none, 1: small, 2: medium, 3: many, 4: serious

[0093]

[Table 2]

[0094]

[Test Example 2] Seed disinfection effect test (disinfection by seed immersion method) on rice infected with Inaba sapling disease fungus Triflumizole- resistant and susceptible rice scabies ( gibberella ) grown in steam-sterilized rice straw medium・ Fujikuroi: Gibberella fujikuroi ) as a spore suspension,
The flowering rice (variety: Nipponbare) was spray-inoculated twice each to obtain paddy rice disease-infected seedling-infected paddy (two types of resistant bacteria-infected rice and susceptible bacteria-infected rice).

Seed Disinfection Method The rice paddy infected with the fungus obtained by the above method was diluted with a predetermined concentration of each chemical solution prepared according to the wettable powder of Example 1 to a ratio of seed rice to chemical solution (V / V). Immersion treatment was performed at 20 ° C. for 24 hours at a ratio of 1: 1. The next day, the drug solution was discarded, and tap water was newly added at a ratio of 1: 2 to the seed rice (V / V), followed by soaking at 20 ° C. for 3 days. Then, the seeds were germinated at 30 ° C. for 24 hours, and were seeded on granular Kumiai soil (180 cm ² per section) in an amount of 5 g per section. After germination treatment at 32 ° C. for 2 days, the plants were transferred to a glass greenhouse and cultivated.

The disease incidence was investigated 30 days after sowing, by examining the number of diseased seedlings and the number of healthy seedlings that exhibited symptoms such as stunting and death of rice seedlings (the total number of seedlings per ward was 350 on average). Seedling rate (%) was determined. From this, as shown in the following formula, the seed disinfection rate (%) was calculated in comparison with the diseased seedling rate (%) in the untreated plot. Regarding phytotoxicity, the emergence rate, growth degree, etc. were observed and indicated by the following phytotoxicity index.

[0097]

[Equation 2] Diseased seedling rate (%) = (Number of diseased seedlings ÷ Total number of investigated leaves) × 100 Seed disinfection rate (%) = {1− (Rate of diseased seedlings in treated area / rate of diseased seedlings in untreated area)} × 100 Injury index O = No injury, 1 = Small, 2 = Medium, 3 = High, 4 =
50 This test was conducted in one treatment and three plots, and the average seed disinfection rate (%)
Is shown in Table 3.

[0098]

[Table 3] Note 1) TMTD is bis (dimethylthiocarbamoyl)
Shows disulfide. Note 2) The values in parentheses in the table indicate the disease severity (%) in the untreated plot.

[0099]

[Test Example 3] Barley Powdery Mildew Control Effect According to the wettable powder of Example 1 on barley seedlings (variety: Akagami Riki) in the 1-leaf stage (using propiconazole and posigrol instead of triadimenol) ) Or a diluted solution of a predetermined concentration of each drug solution prepared in accordance with the wettable powder of Example 3 (using Compound 3 instead of Compound 11), and spray the barley powdery mildew seedling (Erysiphe graminis f. Sp. hordei). After cultivation in a glass room at a temperature of 15-20 ° C. for 10 days, the control value was calculated in the same manner as in Test Example 1 based on the area of the lesion formed on the first leaf. Table 4 shows the results.

[0100]

[Table 4]

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification code FI A01N 43/653 A01N 43/653 J 43/84 101 43/84 101 47/38 47/38 B 47/40 47/40 Z ( 72) Inventor Yukiyoshi Takanichi 1041, Yasu-cho, Yasu-cho, Yasu-gun, Shiga Pref. (72) Inventor Hideo Takeshiba 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga pref. JP, A) (58) Fields surveyed (Int. Cl. ⁷ , DB name) A01N 55/00 A01N 35/06 A01N 43/40 A01N 43/50 A01N 43/653 A01N 43/84 A01N 47/38 A01N 47 / 40 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. A compound of the general formula (I) [Wherein, A represents a 1,2,4-triazol-1-yl group or an imidazol-1-yl group, n represents 1, 2 or 3 (when n is 2 or 3, each represents X may be different), X is a hydrogen atom, a halogen atom, a phenyl group, the same or different lower alkyl group optionally substituted with 1 to 3 halogens, or the same or different 1 to 3 Represents a lower alkoxy group which may be substituted with halogen. A germicidal composition comprising, as active ingredients, at least one selected from the compounds represented by the following formulas or salts thereof, and at least one selected from the following ergosterol biosynthesis inhibitor group (II): Composition. [Biosynthesis inhibitor group (II)] (1RS, 2RS; 1RS, 2SR) -1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,
2,4-Triazol-1-yl) butan-2-ol 1- [2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-ylmethyl] -1H-
1,2,4-triazole (RS) -2- (2,4-dichlorophenyl) -1-
(1H-1,2,4-triazol-1-yl) hexane-2-ol bis (4-fluorophenyl) (methyl) (1H-1,
2,4-triazol-1-ylmethyl) silane (E) -4-chloro-α, α, α-trifluoro-N-
(1-Imidazol-1-yl-2-propoxyethylidene) -O-toluidine N-propyl-N- [2- (2,4,6-trichlorophenoxy) ethyl] imidazole-1-carboxamide cis-4- [ 3- (4-tert-butylphenyl) -2-
Methylpropyl] -2,6-dimethylmorpholine (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,
2,4-triazol-1-ylmethyl) cyclopentanol 2,2-dimethyl-4-chloro-5- (4-chlorobenzylidene) -1-cyclopentanone (2RS, 3RS; 2RS, 3SR) -2- ( 4-chlorophenyl) -3-cyclopropyl-1- (1H-1,
2,4-triazol-1-yl) butan-2-ol 4-chlorobenzyl-N-2,4-dichlorophenyl-
2- (1H-1,2,4-triazol-1-yl) thioacetamidoate 2-p-chlorophenyl-2- (1H-1,2,4-triazol-1-ylmethyl) hexanenitrile pent-4- Enyl-N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone-O-methyloxime (RS) -1-p-chlorophenyl-4 , 4-Dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol 1- (4-chlorophenoxy) -3,3-dimethyl-1
-(1H-1,2,4-triazol-1-yl) butanone 2,6-dimethyl-4-tridecylmorpholine