JPH01308262A - Imidazole based compound and germicide for agriculture and horticulture containing above-mentioned compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R<1> is alkyl which may be replaced with a halogen; R<2> is Cl, Br or I). EXAMPLE:4-Chloro-1-dimethylsulphamoyl-5-n-propylimidazole-2-ca-rbothio amide- S-oxide. USE:An insecticide for agriculture and horticulture. PREPARATION:A compound expressed by formula II is reacted with an oxidant (e.g. hydrogen peroxide, tert. butylhydroperoxide or perbenzoic acid) in a solvent (e.g. methanol, acetone or benzene) at -20-100 deg.C for 0.5-10hr to provide the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel imidazole compounds, methods for their production, and agricultural and horticultural fungicides containing them as active ingredients.

[Disclosure of the invention]

The inventors conducted various tests on imidazole-based compounds and found that a new compound having a force/l i-thioamide-8-oxo1 at the 2-position of the imidazole ring was found.
A saw that shows high sterilizing viscosity.

That is, the present invention provides an imidazole represented by the following formula; Related to system compounds.

In the above formula (1), examples of the alkyl-based halokene atom which may be substituted with the halokene atom represented by R' include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, ``alkyl'' which may be substituted with a halokene atom represented by R1 may also be used as the ar/l ha 1-al group of the piece, and has a carbon number of 1 to 12, such as a methyl group, a conidel group, a propyl group ( , butyl (, pendel, !I), henitosyl, hebutylnonyl, decyl, etc. These alkyl groups also include structural isomers of linear or branched aliphatic chains.

Compound LJ of formula (1) can be produced, for example, by the following production method.

(In the formula, R' and l', !2L'A are as described above.

) The oxidizing agent used in the reaction is hydrogen peroxide;
Examples include hydroperoxides such as t-butylhydroberoxide and t-amylhydroberoxide; organic peroxides such as peracetic acid, perbenzoic acid, and m-chloroperbenzoic acid; the amount thereof is usually - The amount is 0.7 to 2.0 equivalents relative to the compound of formula (II). Furthermore, a metal oxide such as vanadium pentoxide may be added to further promote the oxidation reaction.

n: The reaction in step 1 is carried out in the presence of a solvent at -20 to 100°.
The reaction time was η! Ii10.5~1
It is 0 hours.

Examples of solvents include alcohols such as methanol, ethanol, and t-butanol; amides such as N-methylpyrrolidone; carboxylic acids such as acetic acid; ketones such as acetone; pyridine, picoline, lutidine, Hensen, and chloride. Aromatic (such as Hensen's) carriers include dichloroform, dichloromethane, sulporan, and acetolyl.

The compound represented by the above-mentioned formula (II) can be produced, for example, by the following method.

SO□N(CI+3)2 1 l1I SO3M (C113) z 11?1 (u -b) (B) R' (IV) (III) +1' (wherein, Y is a halogen atom, and Y' is a chlorine atom atom, bromine atom, or iodine atom, and R1 and R2 are as described above.) The compound (Vl) can be produced by halogenating 2-cyanoimidazole with a commonly used halogenating agent. I can do it.

The solvents described in the reactions (A) and (B) include aromatic hydrocarbons such as henzene, toluene, xylene, and chlorohensen; chloroborum, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, n-hexane ( )°n, cyclobeki4no.

Cyclic or acyclic aliphatic hydrocarbons such as diethylnitrile, dioxane, tetrahydrofuran, etc.; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone; acetonitrile; dimethylbormamide, N-methylpyrrolidone, dimethyl Examples include aprotic polar solvents such as sulfoxide and sulfolane. The acid acceptor may be either an inorganic base or an organic base. Examples of the inorganic base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as anhydrous potassium carbonate and anhydrous calcium carbonate. Carbonates of metals or alkaline earth metals; alkali metal hydrides such as sodium hydride; alkali metals such as sodium metal, and organic bases include triethylamine.

The compound of formula (1) above represents (1-a) (1-b), and the compound of formula (II) represents SO□N(C1h)2 (n-a) (n b)
and the compound of formula (III) above is (III-a) (III-b
).

The compound of formula (IV) has a tautomer represented by (1) (wherein R' and R2 are as described above). Therefore, when the compound of the formula (III) is produced using the compound of the general formula (IV) as a raw material, the compound of the formula (III-a) and/or the compound of the formula (III-b) is obtained. It will be done.

Then, using the compound of the -system formula (■I-a) and/or the compound of the -system formula (ITI-b) as a raw material, the -system formula (n
), the above-mentioned - corresponding to the raw material is produced.
A compound of the formula (II-a) and/or a compound of the formula (II-a)
When the compound b) is obtained and the compound of the general formula (1) is produced using the compound of the formula (II-a) and/or the compound of the formula (It-b) as a raw material, the compound of the general formula (1) corresponding to the raw material The compound of the formula (1-a) and/or the formula (1-a)
The compound Ib) is obtained. In this way, for a certain raw material compound that has tautomers, -3O2N (CI+3)
As a result of the reaction in which 2% is introduced, a mixture of two isomers or one or the other is obtained. Whether a mixture or one of the isomers is obtained is determined by the compound used as the raw material, the type of reaction from the raw material to the target product, each reaction condition, etc. If a mixture is obtained, its mixing ratio is similarly determined.

Next, a specific synthesis example of the compound of the present invention represented by the above-mentioned formula (1) will be described.

Synthesis example 1 4. Synthesis of -chloro-1-dimethylsulfamoyl-5n-probylimidazole-2-carbothioamide F-3-oxide (compound No. 2 below) [1] In a four-eye flask under a nitrogen atmosphere, 2-cyano -4,5-dichloro-1-dimethylsulfamoylimidazole 6.0 g and dry tetrahydrofuran 10 18
Prepare 0 mβ and dilute with lye ice-acetone.
Kirin to 1.6Mn-phthyllithium while keeping the temperature below 5°C? and 15.3 mβ was gradually added dropwise. After the dropwise addition was completed, the temperature was maintained at the same temperature for 15 minutes. Next, a solution of 5.7 g of n-propyl cola in TeI/rahydrofuran 1
5 mρ was added dropwise at -70°C or below. After the dropwise addition was completed, the mixture was stirred overnight and gradually returned to room temperature to allow the reaction to continue for one winter.

After the reaction was completed, the reaction mixture was poured into water and diluted with 50% methylene chloride.
The extract was extracted at 0 mff, washed with water, and then dried over anhydrous 1-lium sulfate. Methylene chloride was distilled off, and the residue was purified and separated using silica gel column chromatography.
(using ethyl acetate, once each), melting point 66
2.8 g of 4-chlorol:I-'l-cyano-1-dimethylsulfamoyl-5-n-propylimidazole at ~68°C were obtained.

[2] In the above step [1], put j′,) in a four-eye flask.
2.7 g of 4-chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole.

Charge 4.0 mβ of dioquinone, 10 g of triethylamine, and 0.8 g of pyridine, and add 20 to 25° to this mixture.
Hydrogen sulfide gas was introduced at C for about 30 minutes until the raw material disappeared, and the reaction was completed.

After the reaction was completed, the mixture was poured into water, and the precipitated crystals were filtered off using a Nusoche filter and dried. The crystals were separated by silica gel column chromatography (rfl opening solvent: methylene chloride) to give a 4-
2.3 g of chloro-]-]dimethylsulfamoyl-5-n propylimidazole-2-carbothioamide was obtained.

[3] Anhydrous sodium acetate 2.5. g (5 mmo
+) in acetic acid (30 ml) solution containing 4-chloro-1-dimethylsulfamoyl-5-n- obtained in the above step [2].
Propylimidazole-2-carbothioamide 1.55
g (5 mmol), then 30% hydrogen peroxide solution 0.57 mj! (5 mmol) was added dropwise, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was added to 100 mβ of water and extracted twice with 50 mβ of ethyl acetate.

The organic layer was washed twice with water and then twice with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Moyl-5-n-probylimidazole-2-carbodeoamide-8-oxide (compound No. 2 below) 1
．． 22g was obtained.

Synthesis example 2 4-chloro-5-(3-chloropropyl)
-Synthesis of -1-dimethylsulfamoylimidazole-2-carbothioamide=S-oxide (compound No. 4 below) [1] In a four-eye flask under a nitrogen atmosphere, 2-dia2-4,5-dichloro- 9.4 g of 1-dimethylsulfamoylimidazole and 152 g of dry tetrahydrofuran
Prepare m1 and make 175 with Dora Ice-Acetone.
1.6Mn-phyllithium hexane while keeping the temperature below ℃? Yong? 28.6 ml of IQ was gradually added dropwise. After the dropwise addition was completed, the temperature was maintained at the same temperature for 15 minutes. Then, a solution of 14.3 g of 1-chloro-3-a-tofuran in 31 ml of tetrahydrofuran was added dropwise at a temperature below -70°C.

After the dropwise addition was completed, the temperature was gradually returned to room temperature while stirring overnight to complete the reaction.

After the reaction was completed, the reaction mixture was poured into water, extracted with methylene chloride, washed with water, and then dried over anhydrous sodium sulfate. Thereafter, methylene chloride was distilled off, and the residue was separated using silica gel column chromatography using 244 blue (one time each using methylene chloride and n-hexane-ethyl acetate as the developing solvent). Melting point 102-105
4-ri0-5-(3-chloropropyl)-2- at °C
Cyano-1-dimethylsulfamoylimidazole4.
1g was obtained.

[2] 4-obtained in the above step [1] in a four-eye flask
Chloro-5-(3-chloropropyl)-2-cyano-1
- 2.8 g of dimethylsulfamoylimidazole, 62 ml of dioxane, and 0.9 g of triethylamine were charged, and hydrogen sulfide gas was introduced into this mixture at 20 to 25°C for about 10 minutes, and then stirred at room temperature for 2 hours to complete the reaction. .

After the reaction is complete, the mixture is poured into water, and the precipitated crystals are filtered and dried to obtain a melting point of 118-120°C.
2.5 g of 4-chloro-5-(3-chloropropyl)-1-dimethylsulfamoylimidazole-2-carbothioamide was obtained.

[3] In a four-eye flask, put the 4-obtained in step [2] above.
Chloro-5-(3-chloropropyl)-1-dimethylsulfamoylimidazole-2-carbothioamide O,
f; 9 g, acetic acid 12 mn and anhydrous sodium acetate 1
Prepare 0.228 g of 30% hydrogen peroxide solution at room temperature.
was dripped. After the dropwise addition was completed, the mixture was stirred at room temperature for 3 hours to complete the reaction.

After the reaction is complete, the mixture is poured into ice water, and the precipitated crystals are filtered through a Nusoche and dried to give a melting point of 104 to 106°.
0.43 g of 4-chloro-5-(3-chloropropyl)-1-dimethylsulfamoylimidazole-2-carbodeoamide-8-oxide (Compound 4 described later) of C was obtained.

Representative examples of the compounds of the present invention are shown in Table 1.

Table 1 Compound Let of the present invention, useful as a fungicide for agriculture and horticulture, rice potato r) Iq, rice sheath blight, -1-, J, cucurbit anthracnose, key, - cucurbit powdery mildew, l-71 plague, 171
Symptomosis, (11) black spot of Ai species, mitori mold of columnar fruits, nano-spot, apple spot defoliation, blue-ube leaf spot,
Soil caused by various diseases such as gray mold, sclerotium, and rust, as well as plant pathogenic bacteria such as Fusarium fungi, Pythium fungi, Rhizuktonia fungi, Ticilium fungi, and Plasmodiopora fungi. Shows excellent control effects against diseases. In 2011, various soil diseases such as late blight of potato and potato I, mildew of cucumber and blackberry, blue mold of blackberry, Plasmodiopora spp., Aphanomyces spp., Pisciu J, and F. It shows an excellent control effect against ji'7 damage caused by algae and fungi. The compound of the present invention has a long residual effect and has a preventive effect on cold sores, and also has a therapeutic effect on cold sores, so it is possible to control the disease by post-infection treatment. In addition, since it has osmotic properties, it is also possible to control diseases on grass leaves by soil treatment.

When used, it is the same as in the case of conventional agrochemical formulations.9 In addition to adjuvants, emulsions, powders, wettable powders, liquids, granules,
! ! :i, It can be formulated into various forms such as cloudy preparations. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. Examples of auxiliary agents include carriers, emulsifiers, suspending agents, clouding agents, spreading agents, penetrants, moistening agents, thickeners, stabilizers, etc. Just add it.

Carriers are divided into solid carriers and liquid carriers, and solid carriers include 'rj, 15], sand 117j, cellulose ↑5), Soclodex I/phosphorus, activated carbon, soybean flour (, wheat flour, rice husk powder, wood). Animal and plant products such as powder, fish meal, and milk powder
5) Calcium carbonate, calcium sulfate,
Examples include mineral powders such as thorium bicarbonate, zeolite, diatom, hydrous amorphous silicon dioxide, clay, alumina, silica, and sulfur powder; liquid carriers include water, animal and plant materials such as soybean oil, cottonseed oil, etc. oil, ethyl alcohol,
Alcohols such as ethylene glycol, acetin,
Keynes such as methyl ethyl getone, diio)-
Ethers such as San, TeI-Rahydro Cofuran, aliphatic hydrocarbons such as kerosene, kerosene, and liquid paraffin,
Aromatic hydrocarbons such as xylene, trimethylhembin, tetramethylhembin, cyclohe-1-thane, turchent naphtha, and methylnafculene, halogenated hydrocarbons such as chloroform and chlorohenzene, and acid amides such as dimethylpolamide. , ethyl acetate, esters such as glycerin ester of fatty acids, nitriles such as acetonylyl, sulfur-containing compounds such as dinotyl sulfoxide, N-methylpyrrolidone, N,N-dimethylborumami F, etc. .

A suitable blending weight ratio of the compound of the present invention and the adjuvant is generally 0.05; 99.95 to 90.10, preferably O,
199,8-B (120.

The concentration of the compound of the present invention varies depending on the target crop, usage method, formulation form, application amount, etc. - Although it cannot be generally specified, in the case of foliage treatment, the concentration is 0.1 per active ingredient.
~10,000 ppm, preferably 1-2.00
It is 0 ppm. For soil treatment, '14"rm
l O ~ 100,000 g/ha, preferably
200-20.000 g/ha.

The compound of the present invention may be mixed or mixed with other agricultural chemicals, such as insecticides, acaricides, nematicides, fungicides, anti-virus agents, attractants, herbicides, plant growth regulators, etc., as necessary. ](can be used, and in this case, it may have a negative effect.

For example, as an insecticide, acaricide, or nematocide,
0-(4-1'lomo-2-chlorophenyl)Q-ethyl)
S-bu1cobyl Phosphorothiocony-1,2,2
-dichlorovinyl dimethyl phosphene-1-, ethyl 3-methyl-4-(methylthio)phenyl isopropylvosboroamide 1-1O.

O-dimethyl 0-4--1-rho-m-1-lyl phosborothiony-1., 〇-ethyl 0-4-nitrophenyl phenylbosbothiony-1., 0.0-diethyl 0-2-isopropyl-6- Methylpyrimidine-4-
Il bosborothioate, 0゜0-dimethyl 0-
(3,5,6-1-dichloro-2-pyridyl) bosborothiony 1., O,S-dimethyl acetylbosboroamidethiony 1.,0- (2,4-dichlorophenyl) 0-ethyl S- Organophosphate ester compounds such as propyl bosborodithione 1; 1-naphdylmethyl carhamate, 2-isopropoxyphenylmethyl carbamate, 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime , 2,3-dihydro-2,2-dimethylhenzofuran-7-yl methyl carbamate, dimethyl N, N
' -Cthiobis[(methylimino)carbonyloxy]bisethanimidothioate, S-methyl N-
(Methylcarbamoyloxy)thioace1-imidate, N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenyl methylcarbamate, 2-dimethylamino-5,6- dimethylpyrimidin-4-yl
Carbame-1-based compounds such as dimethyl carbamate, s, s'-2-dimethylamino I-rimethylenebis (thiocarbame-1); 2゜2.2 trichloro-1
, 1-bis(4-chlorophenyl)ethanol, 4-chlorophenyl 2゜4.5-1-dichlorophenyl sulfone; organometallic compounds such as tricyclohexyltine hydroxide; (
R3)-α-cyano-3-phenoxybenzyl (R3)
-2-(4-chlorophenyl)-3-methylbutycy 1
-13-phenoxyhensyl (In2)-cis, 1-
lance-1-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate-1, (R3)
-α-cyano-3-phenoxyhensyl (In2)
-cis,1-lanse-3-(2゜2-dichlorovinyl)-2,2-dimethylcyclopropane-1
・, (R3)-α-cyano-3-phenoxybenzyl
(In2)-cis-3-(2,2-dibromovinyl)-
2,2-dimedylcyclopropane lupoxylene 1.
, (R3)-α-cyano-3-phenoxyhensyl (I
n2)-cis,trans-3-(2-chloro-3,3゜3-trifluoropropenyl)-2,2-dimethylcyclopropane; pyrethroid compounds such as 1-(4-chlorophenyl); )-3-(2,6-
difluorobenzoyl)urea, 1-(3,5-dichloro-4-(3-chloro-5-).lifluoromethyl-
2-pyridyloxy)phenyl)-3-(2,6-difluorobenzoyl)urea, 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea benzoylurea-based compound 12t6rj-butylimino-3-isopropyl-5-phenyl-3,4,5,6-titrahydro 20
-1.3.5-thiadiazin-4-one, trans-5
-(4-chlorophenyl)-N-cyclohexyl-4-
Compounds such as methyl-2-oxothiazolidinone-3-carboxamide, N-methylbis(2,4-xylyliminomethyl)amine; isopropyl (2E, 4.E
)-11-methoxy-3,7,111-limethyl-2,
Juvenile hormone-like compounds such as 4-dodecasinoate:
In addition, examples of other compounds include dinibutyl compounds, organic sulfur compounds, urea compounds, triazine compounds, and the like. Furthermore, it can be mixed or used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, as a fungicide, S-hensyl 0゜0-diisopropylbosborothioate, 0-ethyl S, S-
Diphenyl bosborothioate, aluminum ethylhydrogen Phosphonate-1, O-2,6-dichloro-p-tolyl 0°0-dimethyl Bosborothioate, and other organophosphorus compounds i4,5.6.7-te 1
- Organic chlorine compounds such as laclo-l-cophthalide and tetrachloroisofucronitrile; Manganese polymers of ethylenebis(dithiocarhame-1-), polymers of zinc ethylenebis(dithiocarhame-1), zinc and 7-nebu 311 3a, 4.7.7a-tel, lahydro-N-(+
・Lichloronocunesulfenyl)phthalimide, 3a
, 4.7.7a-Te1rahydro-N-(+,, +,
, 2. 2 N-halokenotioalkyl compounds such as 1-exunsulfenyl)phthalimyl, N-(1-rif 1:1 notylsulfninyl)phthalim; 3 (3 ,,5-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxyrimide, (R3)-3-(
3,,5-dichlorophenyl)-5-notyl-5-vinyl-1,3-dione, N
Dicarboximide compounds such as -(3,5-dichlorophenyl)-i, 2-dimethylsifurob-1-]pan-1゜2-dicarboximide; methyl 1-(butylcarbamoyl)benzimidazol-2-yl 1-(4-chlorophenoxy)-3,
I
H-1,2,4-1-riazol-1-yl)butane-
2-ol, 1-(N-(,1,-ri-l colo-2-1-
1(2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolane-2-
ylmethyl]-111-1,2,4-triazole, 1
-(2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-11■-
1,2,4-1-riazole, 1. -(2-(2゜4-
dichlorophenyl)pentyl)-1H-1.

2. Azole compounds such as 4-1-riazole; 2
．． 4'-dichloro-α-(pyrimidin-5-yl)
Carbinol-based compounds such as benzhydryl alcohol, (±1-2,4'-difluoroα-(], H-1-,2,4-1-lyazol-1-ylmethyl)benzhydryl alcohol; 3 ” -Isobrophonitoshi-
Henzanilide compounds such as o-toluanilide, trifluoro-3'-isopropoxy o-l-ylanilide; methyl N-
(2-methodi1-diacetyl)-N- (2.6-
Acylalanine compounds such as 3-chloro-N-(3-chloro-2,6-
Sinitro 4-α, α. α-l・lifluorotril)−
Viridinamine compounds such as 5-1-lifluoro I-comethyl-2-pyridinamine; and other compounds,
Piperazine compounds, maltumerin compounds, anthraquinone compounds, 6-methyl-1,3-dithiolo (4.
5-b) Quinoxaline compounds such as quinoxalin-2-one, crotonic acid compounds, sulfenic acid compounds, phenylcarhame-1 compounds such as isopropyl-3,4-shedquin phenylcarbamate, and urea. Examples thereof include cyanoacetamine U-based compounds such as 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea, antibiotics, and the like.

Test examples and formulation examples of the agricultural and horticultural fungicide according to the present invention are described below.

The evaluation in the test example was based on the following criteria.

The quasi-controlling effect was determined by visual observation of the degree of disease onset of the test plants during the survey, and the control index was determined using the following five levels.

[Control index] [Severity of disease onset] 5: No lesions are observed 4: The lesion area, number of lesions, or lesion length is less than 1046 in the untreated area 3; The lesion area, number of lesions, or lesion length The length is less than 40% of the untreated area2: The lesion area, number of lesions, or lesion length is less than 70% of the untreated area1: The lesion area, number of lesions, or lesion length is less than the untreated area 70% or more of test MJ11 Gyūlbeto・oka straight elbow and test diameter 7.
Cultivate cucumbers (variety: four-leaf) in 5cm plastic pots,
When the two-leaf stage was reached, the plants were inoculated by spraying with a spore suspension of downy mildew. After 24 hours, 10 mβ of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun. 22~
After being kept in a constant temperature room at 24°C for 6 days, the lesion area on the first leaf was investigated, the control index was determined according to the evaluation criteria, and the second
Obtained the results in the table.

Table 2 5 layers 12 Tomato 1" - 6° diameter" diameter 1..5
Tomatoes (variety: Bonterosa) were grown in cm-sized polyethylene pots, and when they reached the four-leaf stage, 10 mρ of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun.

After being kept in a thermostatic chamber at 22 to 24° C. for one day, a suspension of zoosporangia of Phytophthora Phytophthora was inoculated by spraying. Five days after inoculation, the lesion area was investigated and the control index was determined according to the evaluation test described above, and the results shown in Table 3 were obtained.

Table 3 Formulation Example 1 (a) Compound No. 1, 50 parts by weight (b) Kaolin 40 (c)
A wettable powder can be obtained by uniformly mixing lignin sulfonic acid soda 7 (d) dialkyl sulfonate 1.3 or more.

Formulation Example 2 (a) Compound No. 2 20 parts by weight (
b) Kaolin 72 (c) Sodium lignin sulfonate 4 (d) Polyoxyethylene alkyl allyl ether
4. Wettable powders can be obtained by uniformly mixing the above ingredients.

Formulation Example 3 (-) Compound No. 3 6 parts by weight (b) Diatoms ± 89 to (c) Dialkyl sulfosuccine-1, 2 (d) Polyoxyethylene alkylphenyl ether sulfe 1-4 The above Wettable powders can be obtained by uniformly mixing the ingredients.

Formulation example 4 (a) Kaolin 78 parts by weight (b)
β-Nafuku 1/Sodium sulfonic acid polymerin condensate
2 (c) Polyoxyethylene alkyl allyl phenylene fluoride 1.5 (d) Hydrous amorphous silicon dioxide 15 ...The mixture of each of the components in 2 below and compound No. 4 in a weight ratio of 4=1 to obtain a wettable powder.

Formulation Example 5 (a) Compound No. 4 5 parts by weight (
b) Talc 94.57/
(iii) HIXm alcohol phosphate ester (0.57) A powder can be obtained by uniformly mixing the two ingredients.

Formulation Example 6 (a) Compound No. 2 20 parts by weight (
b) Xylene 60 (c) Polyoxyethylene alkyl allyl ether
An emulsion is obtained by mixing and dissolving the above components.

Formulation Example 7 (a) Compound No. 4 1 part by weight (
(b) Bentonite l-61 (c) Kaolin 33 (d) Sodium lignin sulfonate 5 An appropriate amount of water required for granulation is added to each of the above components, mixed and granulated to obtain granules.

Claims (1)

[Claims] 1. General formula: ▲There are numerical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1 is an alkyl group that may be substituted with a halogen atom, and R^ 2 is a chlorine atom, a bromine atom, or an iodine atom. 2. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1 is an alkyl group that may be substituted with a halogen atom, and R^2 is a chlorine atom, bromine atom An agricultural and horticultural fungicide characterized by containing as an active ingredient an imidazole-based compound represented by the following formula: atom or iodine atom. 3. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 is an alkyl group that may be substituted with a halogen atom, and R^2 is a chlorine atom, a bromine atom, etc.) A general formula characterized by the reaction of a compound represented by an atom or an iodine atom with an oxidizing agent: ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^ 1 and R^2 are as described above.) A method for producing an imidazole compound represented by