JPH0717817A - Funigcidal composition comprising silicon-containing azole-based compound - Google Patents

Abstract

PURPOSE:To obtain an agricultural and horticultural mixed fungicide having a wide antimicrobial spectrum and a synergistic effect, preventing development of resistant microorganisms by combining a silicon azole-based compound with an ergosterol biosynthesis inhibitor. CONSTITUTION:A fungicidal composition comprises one or more selected from a silicon azole-based compound of the formula [A is 1,2,4-triazol-1-yl or imidazolyl; (n) is 1-3; X is H, halogen, phenyl, (halogenated)alkyl or (halogenated) alkoxyl] and its salt and one or more selected from an ergosterol biosynthesis inhibitors as active ingredients. (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 may be cited as the ergosterol biosynthesis inhibitor.

Description

Detailed Description of the Invention

[0001]

OBJECT OF THE INVENTION It is an object of the present invention to provide an agricultural / horticultural compounded bactericide having a broad antibacterial spectrum, having a synergistic effect and preventing the development of resistant bacteria.

[0002]

FIELD OF THE INVENTION The present invention relates to a novel fungicidal composition for agricultural and horticultural use which comprises a combination of a silicon-containing azole compound and an ergosterol biosynthesis inhibitor and has an excellent fungicidal effect.

[0003]

The compound (I) used as the active ingredient of the present invention is described in Japanese Patent Application No. 4-267234.

These compounds have therapeutic and preventive effects against many plant diseases, and when used as a spraying agent or a water-applying agent, they can effectively suppress the blight and blast, which are important diseases of rice cultivation. Can be controlled. In addition, by using it as a soil treatment or seed treatment agent, Rhizoc
In addition to controlling dead-end disease of various crops such as beet, cotton, wheat, cucurbits, and legumes caused by tonia fungus, soil such as white silk disease of eggplants and cucurbits, black rot of potatoes, and eye-spot of wheat. Infectious diseases can be effectively controlled.

The other compound group (II) used as the active ingredient of the present invention (II) (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-dioxolane-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) hexan-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) thioacetamidate 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 “pyriphenox”) (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,
"Tridemorph") (hereinafter, these compounds of group (II) are collectively referred to as "ergosterol biosynthesis inhibitors") are agricultural and horticultural fungicides having an activity of inhibiting fungal ergosterol biosynthesis. It is well known and has been used as a spraying agent, seed treating agent or soil treating agent for controlling various diseases such as vegetables, fruit trees and grains. These drugs have excellent antibacterial spectra and have excellent properties that they do not show phytotoxicity to various crops at practically used concentrations.

[0006]

However, the compound (I) and the ergosterol biosynthesis inhibitor (II) are
If it is applied in a too large amount, there is a risk of causing chemical damage such as growth inhibition. Further, when the ergosterol biosynthesis inhibitor (II) is repeatedly used for a long period of time, pathogenic bacteria with reduced susceptibility to these agents may appear. For example, the udon noodles of wheat and vegetables, which have been effective so far, may appear. It is difficult to control the disease and the rice seedling disease.

The present inventors have found that the compounding agent of the present invention exerts an unexpectedly enhancing effect on various diseases, and that the compounding agent of the present invention has a synergistic enhancing effect. The present invention has been completed.

[0008]

[Constitution of the invention]

[0009]

The present invention has the general formula (I)

[0010]

[Chemical 2]

[Wherein A represents a 1,2,4-triazol-1-yl group or an imidazol-1-yl group, and n
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, the same or different 1 to 3 It represents a lower alkyl group optionally substituted with halogen or a lower alkoxy group optionally substituted with 1 to 3 halogens which are the same or different. ] One or more selected from the compound represented by the formula or a salt thereof, and 1 selected from the group (II) of ergosterol biosynthesis inhibitors described below.
A bactericidal composition containing at least one species as an active ingredient.

[Group (II) of biosynthesis inhibitors] (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) hexan-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) thioacetamidate 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 formula (I) above, the "halogen atom" for X is 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 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 or isopentyl. , 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,
Carbon number 1 such as 2,3-dimethylbutyl and 2-ethylbutyl
To 6 straight or branched chain alkyl groups, preferably 1 to 4 carbon straight or branched chain alkyl groups,
More preferably, it is a methyl or ethyl group.

In the above formula (I), the "lower alkyl group which may be substituted with 1 to 3 halogens which are the same or different" is not limited to the above-mentioned unsubstituted "lower alkyl group" but also includes, for example, Trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, 2,2,2-trichloroethyl, 2,2,2-
The aforementioned "lower alkyl group" such as trifluoroethyl, 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl, 2,2-dibromoethyl, chloropropyl, trifluoropropyl, fluorobutyl, trichloropentyl, trifluorohexyl. Is a group in which 1 to 3 halogen atoms which are the same or different are substituted. At this time, as the lower alkyl group substituted with the same or different 1 to 3 halogens, it is preferable that the same halogen atom is 1 to 3 in the linear or branched alkyl group having 1 to 3 carbon atoms. A group in which one or three fluorine or chlorine atoms are substituted in a methyl or ethyl group is more preferable, and a trifluoromethyl group is most preferable.

In the above formula (I), the "lower alkoxy group" for 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 or branched chain alkoxy group having 1 to 6 carbon atoms such as 1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy and 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 which may be substituted with 1 to 3 halogen atoms which are the same or different" is not limited to the above-mentioned unsubstituted "lower alkoxy group" but also includes, for example, 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 "lower alkoxy group" such as trifluorohexyloxy is a group in which 1 to 3 halogen atoms which are the same or different are substituted. At this time, the lower alkoxy group substituted with the same or different 1 to 3 halogens is preferably a straight-chain or branched alkoxy group having 1 to 3 carbon atoms and the same halogen atom being 1 to 3 A group in which 1 to 3 fluorine or chlorine atoms are substituted in a methoxy or ethoxy group, and a trifluoromethoxy group is most preferable.

In the above 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, and more preferably 1.

In the above general 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 the 2-position, 4-position, or 2, -position of the benzene ring.
It is fourth, and more preferably fourth.

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]

[Chemical 3]

[0023]

[Table 1] ──────────────────────────────────── Compound number 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 6 1,2,4-triazol-1-yl 4-CF ₃ 7 1,2,4-triazol-1-yl 4-OCH ₃ 8 1,2,4-triazol-1- Il 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- Il 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 imizosol-1-yl H 40 imizosol-1-yl 4-Cl 41 imizosol- 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 Imidazole-1-yl 2,4-F ₂ 51 Imidazole-1-yl 2-Cl, 4-F 52 Imidazole-1-yl 2-F, 4-Cl 53 Imidazole-1-yl 2 -OCH ₃ 54 Imidazole-1-yl 2-Cl 55 Imidazole-1-yl 2-F 56 Imidazole-1-yl 2,6-Cl ₂ 57 Imidazole-1-yl 2,6-F ₂ 58 Imidazole-1- Ill 2-Cl, 6-F 59 Imidazole-1-yl 3-OCH ₃ 60 Imidazole-1-yl 3-Cl ────────────── ─────────────────────── Of the above exemplified compounds, 1, 2, 3, 4,
5, 6, 9, 11, 12, 13, 14, 15, 16, 1
Nos. 7, 18, and 19 compounds, more preferably 1,
The compounds of Nos. 2, 3, 6, 11, 12, 13, and 14 are most preferred, and the compounds of Nos. 2, 3, 12 are most preferred.

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

[0025]

[Chemical 4]

[In the above scheme, A, X, and n
Represents the same meaning as described above, and M represents a lithium atom or MgZ.
Represents a group (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. ] Each step will be described in more detail below.

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

Ketone (VII) can be obtained from JP-B-63-460.
It can be manufactured according to the method described in JP-A-75.

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

This step is carried out 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, relative to the compound of the formula (VII). Is.

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

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

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

(Method B) In Step B-1, the ketone (IV) is used.
Is a step of producing the compound (V) by adding the silyl compound (III) to, and can be performed according to the step A.

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 give compound (I) of the present invention via epoxide (VI). Is.

The reaction is carried out by reacting 1 equivalent or more of 1,2,4-triazole or imidazole with respect to the compound of the general formula (V) in a solvent in the presence of 1 equivalent or more of a base, or It is carried out by reacting a basic salt of 2,2,4-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, but preferably, it is an aliphatic carbonization such as hexane, heptane, ligroin or petroleum ether. Hydrogen; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane , Ethers such as dimethoxyethane, 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, 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 alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate and carbonic acid are preferred. Alkali metal hydrogen carbonate such as potassium hydrogen; Alkali metal hydride such as lithium hydride, sodium hydride, potassium hydride; Sodium hydroxide, potassium hydroxide,
Alkali metal hydroxides such as barium hydroxide; sodium methoxide, sodium ethoxide, bota-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
U) or an organic metal base such as butyllithium or lithium diisopropylamide,
More preferred are alkali metal carbonates such as sodium carbonate and potassium carbonate.

In order to effectively carry out the reaction, quaternary ammonium salts such as benzyltriethylammonium chloride and tetrabutylammonium chloride,
It is also possible to add alkaline earth metal halides such as sodium iodide, sodium bromide and lithium bromide, crown ethers such as dibenzo-18-crown-6-, and the like.

The reaction temperature is −78 ° C. to 200 ° C., preferably −20 ° C. to 150 ° C.

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

The ketone of (IV) is Beilsteins Handbuc
It can be produced according to the method described in h der Organischen Chemie, 7 , 285, 7 , 283.

The mixing ratio of the compound (I), which is the active ingredient of the composition of the present invention, and the ergosterol biosynthesis inhibitor (II) can be varied within a relatively wide range, but usually the azole derivative (I) is 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, spraying,
Compound (I) and ergosterol biosynthesis inhibitor (II) for surface application or treatment of soil or seed,
It can also be used individually within a short period of time.

The admixtures of the present invention are usually used together with the auxiliaries customarily used in the pharmaceutical field. The active ingredients of the azole derivative (I) and the ergosterol biosynthesis inhibitor (II) can be prepared by known methods, for example, emulsion stock solutions, sprayable pastes,
It can be formulated as sprayable or dilutable solutions, emulsions, wettable powders, water solutions, powders and capsules, eg with polymeric substances. Also, for the purpose of labor saving and safety, etc., an agrochemical formulation that is easily dispersed or dissolved in water or on the surface of water (granules,
It is also possible to coexist with a suitable water repellent, foaming agent, spreading agent, etc. in the form of tablets, wettable powders, capsules, etc., and directly wrap this in water-soluble paper and throw it into water.

The above-mentioned preparation is applied as it is or diluted with water or the like, and applied to the plant or water surface, or applied to soil.

That is, the above-mentioned preparation is sprayed or dusted on a plant, sprayed on the water surface of a paddy field or the surface of soil, dusted or granulated, or if necessary, further mixed with soil in various forms. Can be used.

When used as a seed treatment agent,
It can be used after seed dressing treatment, seed dipping treatment and the like. In addition, it can be expected to enhance the bactericidal effect by mixing with other bactericides.

Further, other fungicides, insecticides, acaricides,
It can also be used simultaneously with or without mixing 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, uplands, orchards, meadows, lawns 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 form, application time, method, place, target disease, target crop, etc., but is usually 0.01 g per are. 1000 g, preferably 0.1 g
It is 100 g, and when an emulsion, a wettable powder, a suspending agent, a liquid agent or the like is diluted with water and applied, the application concentration is 0.0001.
-1%, preferably 0.001-0.5%. Granules, powders, etc. are applied as they are without any dilution.

For seed treatment, the total amount of active ingredients is, for example, about 0.001 to about 50 g per 1 kg of seeds.
Preferably about 0.01 to about 10 g can be used.

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

In surface treatment of paddy fields, the total amount of active ingredients may be, for example, about 0.001 to about 40 kg, preferably about 0.01 to about 10 kg per hectare. When processing the nursery box, one box (80 cm x 60
cm × 8 cm) about 0.1 to about 1 as the total amount of active ingredients
00 g, preferably about 0.1 to about 50 g can be used.

When the composition of the present invention is used in rice cultivation, it can be used from the time when the rice seedlings are grown in the nursery box to the harvest after rice planting, and the effect is long-lasting. .

[0057]

EFFECTS OF THE INVENTION The compounded fungicide of the present invention is effective against plant diseases caused by the following fungi, for example.

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

[0059]

EXAMPLES The present invention will be described in more detail below with reference to Examples, Reference Examples and Test Examples, but the compounds, additives and their compounding ratios in the Examples are not limited to these. In addition,% used in the examples is% by weight unless otherwise specified.

[0060]

Example 1 (Wettable powder) 20 parts of triadimenol, 20 parts of compound 3 (showing compound numbers in Table 1, the same applies hereinafter), white carbon 2
0 part, 3 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate 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, Using a homomixer, mix and disperse evenly,
Further, 10 parts of 2% xanthan gum aqueous solution is added and stirred,
A flowable agent was obtained.

[0064]

[Example 5] (Wettable powder) 10 parts of triadimenol, 10 parts of triflumizole,
20 parts of compound 3, 20 parts of white carbon, 3 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate and 35 parts of clay were mixed and sufficiently 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. It was sufficiently pulverized to obtain a wettable powder.

[0066]

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

[0067]

[Example 8] (Wettable powder) 10 parts of triflumizole and 10 parts of triadimenol were added.
Parts, 10 parts of compound 2, 10 parts of white carbon, 5 parts of sodium alkylbenzene sulfonate and 55 clay
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) into 2- (1H-1,2,2,1) 4-triazol-1-yl) acetophenone (0.505
g, 2.7 mmol) was added and the solution was stirred at room temperature under a nitrogen stream, and trimethylsilylmethylmagnesium chloride (tetrahydrofuran 1 mol solution 13.5 ml, 13.5) 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, then heated under reflux for 6 hours, then cooled and cooled with ice water (10
0 ml) and adjusted to pH 6 with 5% hydrochloric acid, ethyl acetate (3 x
It was extracted with 50 ml). The organic layers were combined and saturated brine (3 x
After washing with water (50 ml), the organic layer is dried (Na ₂ So ₄ ) and evaporated to give a crude oily substance. Purification is performed by silica gel column chromatography (ethyl acetate: hexane = 1: 1 → 2: 2).
It was subjected to 1) to give the title compound. 0.112 g (15% yield) (Preparation 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 ~ 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,
4-Triazol-1-yl) -3-trimethylsilyl-2-propanol To dimethylformamide (60 ml), 60% sodium hydride (1.62 g, 0.04 mol) was added, and the mixed solution was cooled and stirred with ice water. Bottom 1,2,4-triazole (2.91 g, 0.04 mol) is added. The reaction mixture was further stirred at room temperature for 30 minutes, then 1-chloro-2- (4-fluorophenyl) -3-obtained in Reference Example 1.
Trimethylsilyl-2-propanol (5.5 g, 0.
021 mol) and the mixture is heated with stirring at 90 ° C. for 30 minutes. Then cool and pour into ice water (200 ml),
Extract with ethyl acetate (300 ml), wash the ethyl acetate layer with saturated brine (100 ml x 3) with water, dry the ethyl acetate layer (Na ₂ SO ₄ ) and evaporate to give a crude oil. Chromatography (ethyl acetate: hexane = 1: 5 → 1: 1 → 2: 1) gave the title compound. 2.9 g (yield 47%) (Production method B) Melting point 118-119 ° C NMR spectrum (CDCl ₃ ) δppm: -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 ~ 7.01 (2H, m), 7.26 ~
7.31 (2H, m), 7.91 (1H, s), 7.99 (1H, s) Mass spectrum (M / Z): 293 (M ⁺ ), 278,211 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-Bromphenyl) -1- (1H-1,2,4
-Triazol-1-yl) -3-trimethylsilyl-
2-Propanol yield 11%, melting point 120-121 ° C NMR spectrum (CDCl ₃ ) δppm: -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 spectrum (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 ) δppm: -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%, melting point 97-100 ° 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 yield 8%, mp 144 ° C. NMR spectrum _{(CDCl 3) δppm: -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 = 14.8Hz), 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 Yield 13%, melting point 85-87 ° C NMR spectrum (CDCl ₃ ) δppm: -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-methoxyphenyl) -1- (1H-1,
2,4-Triazol-1-yl) -3-trimethylsilyl-2-propanol Yield 12%, melting point 91-92 ° C NMR spectrum (CDCl ₃ ) δppm: -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,
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 Yield 12%, melting point 135-136 ° C NMR spectrum (CDCl ₃ ) δppm: -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 ) δppm: -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 ~ 6.79 (1H, m), 7.40 ~ 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 ) δppm: -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 ) δppm: -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 spectrum (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 ) δppm: -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,
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 stirred in a nitrogen stream with stirring trimethylsilylmethylmagnesium chloride (ether solution 200 ml, 0.057 mol)
Is added dropwise at a rate such that the temperature of the reaction mixture does not exceed 15 ° C to 20 ° C, and then the mixture is stirred at room temperature for 1 hour. The reaction solution is ice water 2
The mixture was poured into 00 ml, adjusted to pH 6 to 7 with 5% hydrochloric acid and added with 100 ml of ethyl acetate for extraction.
The organic layer was dried (Na ₂ SO ₄ ) and evaporated to obtain a crude oily substance. Purification was performed by silica gel column chromatography (ethyl acetate: n-hexane = 1: 10 → 1 :). 5)
The oily matter of the title compound (8.8 g, yield 67.7%) 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: δppm (CDCl ₃ ) −0.18 (9H, s), 1.23 (1H, d, J = 14.7Hz), 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 Control Effect Using beet (variety: Monohill) at the 6-leaf stage, the area of one ward was set to 5 m ^2, and the test was carried out in triplicate.

Inoculation of the diseased bacteria was carried out by shredding the diseased leaves in the field where the benzimidazole-based drug was continuously sprayed and inoculating the entire test field on June 25. Drug spraying starts from July 10 1
It was sprayed 3 times at intervals of 4 days. 20 days after the final application 1
Regarding 0 strain, the degree of occurrence of beet brown spot disease was investigated according to the following disease index, and the disease degree was calculated by the following formula. Based on this, the control value (%) was calculated from the comparison with the non-scattered area.

Disease index (degree of disease occurrence) 0: No lesions 1: Disease occurs in less than 10% of the leaf area 2: Disease occurs in 10% or more and less than 40% of the leaf area 3: 40% or more and less than 70% of the leaf area Illness 4: 70% or more of the leaf area is ill

[0091]

[Equation 1] degree of disease (%) = (Σ (disease index × number of strains)) ÷
(4 x total number of investigated leaves) x 100 Control value (%) = {1- (disease level of treated plot ÷ disease spread of non-dispersed plot)} x 100 Investigation of phytotoxicity was carried out according to the following index. The results are shown in Table 2.

Chemical damage index 0: none, 1: small, 2: medium, 3: large, 4: severe

[0093]

[Table 2]

[0094]

[Test Example 2] Seed disinfection effect test against paddy rice seedling fungus infected rice (disinfection by seed dipping method) Triflumizole resistant rice bran disease fungus and susceptible rice diarrhea fungus ( gibberella ) cultured in rice straw medium sterilized by test seed steam・ Fujikuroi: Gibberella fujikuroi ) as a spore suspension,
The rice (cultivar: Nihonbare) at the flowering stage was sprayed and inoculated twice each to obtain rice paddy-rice seedlings infected rice (two types of rice, resistant rice infected rice and susceptible rice infected rice).

Seed disinfection method Rice bran disease fungus-infected paddy rice obtained by the above method was added to the seed paddle-to-liquid solution ratio (V / V) in a diluted solution of a predetermined concentration prepared according to the wettable powder of Example 1. Immersion treatment was performed at a ratio of 1: 1 at 20 ° C. for 24 hours. The next day, the chemicals were discarded, and tap water was newly added at a ratio of 1: 2 to seed paddy (V / V), and the seeds were soaked at 20 ° C. for 3 days. After that, germination treatment was carried out at 30 ° C. for 24 hours, and 5 g of each Kumiai granular soil (180 cm ² per ward) was sown. After germination treatment at 32 ° C. for 2 days, it was transferred to a glass greenhouse for cultivation management.

The disease occurrence survey was carried out 30 days after sowing by investigating the number of diseased seedlings and healthy seedlings that showed symptoms of rice bran seedling disease such as maternity and death (the total number of seedlings per ward was 350 on average). The seedling rate (%) was calculated. From this, as shown by 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, the degree of growth, etc. were observed, and the following phytotoxicity index was displayed.

[0097]

[Formula 2] Diseased seedling rate (%) = (Number of diseased seedlings / Total number of surveyed leaves) x 100 Seed disinfection rate (%) = {1- (Rate of diseased seedlings in treated area / Rate of diseased seedling in untreated area)} x 100 Drug damage index O = no drug damage, 1 = small, 2 = medium, 3 = large, 4 =
50 This test is conducted in a system of 1 treatment and 3 wards, and average seed disinfection rate (%)
Is shown in Table 3.

[0098]

[Table 3] Note 1) TMTD is bis (dimethylthiocarbamoyl)
Indicates a disulfide. Note 2) The figures in parentheses in the table indicate the disease incidence (%) in the untreated plot.

[0099]

[Test Example 3] Control effect on barley powdery mildew The barley seedlings (cultivar: Akakami Riki) at the 1-leaf stage were prepared according to the wettable powder of Example 1 (using propiconazole and posigrolol instead of triadimenol). ) Or a wettable powder of Example 3 (compound 3 in place of compound 11) was prepared and sprayed at a predetermined concentration of each drug solution, and the next day, barley powdery mildew (Erysiphe graminis f. Sp. hordei) and sprinkled with conidia. After culturing in a glass chamber at a temperature of 15 to 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. The results are shown in Table 4.

[0100]

[Table 4]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display area A01N 43/653 C 9155-4H B 9155-4H 43/84 101 9155-4H 47/38 B 9155- 4H 47/40 Z 9155-4H (72) Inventor Yukiyoshi Takahisa 1041 Yasu-cho, Yasu-gun, Shiga Prefecture In-house (72) Inventor Hideo Takeshiba 1041 Yasu-cho, Yasu-cho, Yasu-gun In-house, Sankyo Stock Company

Claims (1)

[Claims] 1. A compound represented by the general formula (I): [In the formula, A represents a 1,2,4-triazol-1-yl group or imidazol-1-yl group, and n represents 1, 2 or 3 (when n is 2 or 3, 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 halogen, or the same or different 1 to 3 Represents a lower alkoxy group which may be substituted with halogen. ] One or more selected from the compound represented by the formula or a salt thereof and one or more selected from the group (II) of the following ergosterol biosynthesis inhibitors, as an active ingredient: Composition. [Group (II) of biosynthesis inhibitors] (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) hexan-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) thioacetamidate 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