JPS61126071A - Phenoxyisobutyric acid amide derivative, and agricultural and horticultural fungicide - Google Patents

Abstract

NEW MATERIAL:A phenoxyisobutyric acid amide derivative shown by the formula I {R is lower alkyl, halogen, CF3, NO2, or lower alkoxy; n is 0-3 integer; Het is pyridine ring, pyrimidine ring, isooxazole ring, isothiazole ring, thiadiazole ring, or quinoline ring which man contain substituent group (each group in R except CF3)}. EXAMPLE:N-(4,6-Dimethylpyridin-2-yl)-alpha-(4-chlorophenoxy)isobu-tyric acid amide. USE:An agricultural and horticultural fungicide applicable to a wide range of blights, usable by application into water, or soil application besides foliage dispersion, having both preventing a remedying effects, having neither toxicity to human and animals not toxicity to fishes. PREPARATION:A compound shown by the formula II or its reactive derivative is reacted with a compound shown by the formula III in a proper solvent such as acetone, etc., in the presence of a reaction auxiliary such as triethylamine, to give a compound shown b the formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION A) Reward Ll Two Stands ■Plate■ The present invention relates to a novel phenoxyisobutyric amide derivative, which is useful as a fungicide for agriculture and horticulture.

J and Ryo 1 As a compound similar to the phenoxyisobutyric acid amide derivative of the present invention, an N-substituted monoheterocyclic monophenoxypropionic acid amide derivative has activity as a herbicide in German Published Patent Application No. 3101889AI. is listed. However, there is no mention of bactericidal action.

Conventional phenoxy fatty acid amide derivatives have herbicidal activity and cause strong phytotoxicity to useful crops, and iRm
The present invention provides phenoxyisobutyric acid derivatives and agricultural and horticultural fungicides that are novel and highly practical as agricultural and horticultural fungicides in place of these conventional derivatives.

On the other hand, various compounds have been conventionally used as agricultural and horticultural fungicides, but due to the development of resistance due to continuous use and the emergence of specific diseases due to continuous cropping, the number of diseases that are difficult to control without using new agents is increasing. The creation of a strong compound with a new structure has been long-awaited.The present invention aims to meet these needs and solve various problems in the field of agricultural and horticultural fungicides.

The present inventors, in place of the conventional heptanoxy fatty acid derivative,
A new phenoxyisobutyric acid amide derivative was synthesized and its practicality in the agricultural and horticultural fields was intensively investigated. As a result, it was discovered that the phenoxyisobutyric acid amide derivative represented by the general formula CI) is a new compound that has not been described in any literature, and that the above-mentioned problems can be solved by using these compounds.

(R) n (,;f13 where R is a lower alkyl group, a halogen atom, a CF3 group,
No2 group, lower alkoxy group, n is O~3 Ma
, Het is a lower alkyl group, a halogen atom, No
Indicates a pyridine ring, pyrimidine ring, isoxazole ring, isothiazole ring, thiadiazole ring, or quinoline ring substituted or unsubstituted with a group selected from two groups.

The compound of general formula CI) is superior to known similar compounds in both agricultural and horticultural fungicidal activity and phytotoxicity. That is, the compound of general formula CI) can be used in useful crops such as rice, barley, wheat, sugar beet, cucumber, eggplant, melon, capocha, pea, citrus, green bean, green onion, strawberry, apple, cotton, rapeseed, peach, etc. It can control various diseases without causing chemical damage. A wide range of diseases can be applied, such as rice blast, rice sesame leaf blight, rice sheath blight, sugar beet seedling blight,
These include cucumber seedling blight, cucumber powdery mildew, apple powdery mildew, wheat powdery mildew, barley rust, strawberry gray mold, and peach gray mold. The compound of the present invention has particularly high control activity against rice blast and sesame leaf blight, and also shows high control activity against downy mildew and seedling blight of rapeseed crops.The compound of the present invention is usually sprayed on the foliage of crops. However, since it has permeability, it can also be applied to water or soil to control various diseases. In addition, the compound of the present invention has both preventive and therapeutic effects, and can effectively control diseases if applied before or after the outbreak of the disease. Non-toxic and non-toxic to fish.

(Production method of the present compound) The phenoxyisobutyric amide represented by the formula (I), which is the first aspect of the present invention, is produced by the following reaction.

[■] [■] In general formula (I), [■], (m), Rln, Het
has the same meaning as above.

In order to produce the compound CI) of the present invention, first, the general formula (I
The heterocyclic amine (Ir) is dissolved in a suitable solvent such as evaporate, benzene, toluene, xylene, chlorobenzene, dioxane, tetrahydrofuran, methylene chloride, acetone, chloroform, methyl alcohol, etc., and an equivalent amount or a slight excess thereof is added. Phenoxyisobutyric acid or its reactive derivative of the general formula (n) is added as is or dissolved in an organic solvent such as benzene. The reactive derivatives of phenoxyisoacetic acid of the general formula (n) that are used include acid anhydrides, acid chlorides, acid bromides, and esters, which can be easily prepared from phenoxyisoacetic acid by applying known methods. can be obtained.

In addition, heterocyclic amines of general formula (II[) and general formula [■
] When reacting with phenoxyisobutyric acid or its reactive derivative, appropriate reaction aids such as thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, dicyclohexycarposiimide, triethylamine, pyridine, N-methylmorpholine, quinoline, N,N-dimethylaniline, N,N-diethylaniline, sodium hydroxide, sodium carbonate, sodium methylate, and the like can be used. These reaction aids are preferably selected and used depending on the type of phenoxyisoacetic acid or its reactive derivative.

The reaction is carried out at room temperature or while cooling or heating under reflux as necessary. 0. To complete the reaction, remove the reaction product of the reaction aid by filtration or washing with water, and distill off the used organic solvent. The compound of the present invention has the general formula (,
The phenoxyisobutyric acid 7mide derivative I) can be obtained with good purity and high yield. This compound further contains acetone,
It can be further purified by recrystallization with methyl alcohol, ethyl alcohol, benzene, toluene, chloroform, etc.

2-amino-4,6-
Add 1.3 g (10.6 mmol) of dimethylpyridine, 1.2 g (11.8 mmol) of triethylamine, and 15 ml of acetone, and cool with ice water to bring the internal temperature to 5°C. -chlorophenoxy)
2.33 g (10.0 mmol) of isoacetic acid chloride was dissolved in 77 tons of 5 mfL and added dropwise over 5 minutes. During this time, keep the internal temperature at 5-8℃. 0 After the dropwise addition, stir at room temperature for 15 minutes, then heat and reflux for 20 minutes to complete the reaction. After cooling the reaction solution to room temperature, 1 distill the acetone in the reaction solution. 10 mM of water is added to this, and further 15 mjL of ethyl acetate is added. The contents were transferred to a separatory funnel, the aqueous layer was removed, and 5 ml of water was added and mixed.
Remove the aqueous layer.

Separate the ethyl acetate layer, add 2 g of Glauber's salt to it, mix well, dry, and filter. By distilling off the ethyl acetate from the filtrate, the desired N-(4,6-dimethylpyridine-2-
yl)-α-(4-chlorophenoxy)isoflm amide 3, 1 g (FF rate 97%) was obtained in the form of crystals,
The melting point was 64.5-66°C.

1.1 g (10.19 mmol) of 2-amino-4-methylpyridine, 1.4 g (17.07 mmol) of anhydrous sodium charcoal, and 15 mJL of tetrahydrofuran are placed in a 50 mJL four-hole flask with a diameter of ΩΔ. While stirring,
From a separating funnel, 2.68 g (10.0 mmol) of α-(2,4-dichlorophenoxy)isoacetic acid chloride was dissolved in 5 mfL of tetrahydrofuran and added dropwise over 5 minutes. The mixture was stirred at room temperature for 20 minutes to react, then heated and refluxed for 40 minutes.The reaction solution was returned to room temperature and filtered.
When the acetone in the filtrate was distilled off, 3.33 g (yield 98%) of the target N-(4-methylpyridin-2-yl)-α-(2,4-dichlorophenoxy)isobutyric acid amide was obtained in the form of an oil. and showed rLo 1.5778.

1.64 g (10.0 mmol) of 2-7 minnow 3.5-dichloropyridine, 1.21 g (10.0 mmol) of N,N-dimethylaniline, and 15 m of toluene were placed in a 6250 ml four-bottle flask. Cool to 8°C with ice water. To this, 2.61 g (10,0
mmol) toluene 5m! Dissolve in L and drip over 5 minutes. Stir for 15 minutes at room temperature to react, then heat and react at 80°C for 1 hour. The reaction solution is returned to room temperature, filtered to remove dimethylaniline hydrochloride, and the toluene in the filtrate is distilled off. N-(3,5-dichloropyridin-2-yl)-α7(3,5-dimethyl-4-chlorophenoxy)isobutyric acid amide 3.85 g (yield 9
9%) is obtained in the form of crystals. When this was reconstituted with acetone, the melting point was 72-74°C.

-4-Rolof Noxy Iso Amide -167 0.99 g (10° 1 mmol) of 3-amino-5-methylisoxazole in a 50 ml four-neck round bottom flask.
, 1.0 g (10.0 mmol) of triethylamine and 1-5 m of acetone were added, and cooled with ice water to bring the internal temperature to 5.
℃ 0 Next, from the separating funnel, α-(3,5-dimethyl-4-chlorophenoxy)isoacetic acid chloride F2.6
1 g (10.0 mmol) is dissolved in 5 mM acetone and added dropwise over 5 minutes. After stirring at room temperature for 15 minutes, heat to reflux for 20 minutes.

After the reaction solution was returned to room temperature, the acetone was distilled off, and 10 ml of water and 15 ml of ethyl acetate were added thereto, mixed well and transferred to a separating funnel, and the aqueous layer was removed. The ethyl acetate layer is washed with water and ICmfL, and the aqueous layer is removed. Separate the organic layer, add 2 g of Glauber's salt to it, mix, dry, and filter. When the ethyl acetate in the filtrate is distilled off, the target N
-(5-methylisoxazol-3-yl)-α-(
3.20 g (yield: 99%) of 3.5-dimethyl-4-chlorophenoxy)isoacetic acid amide was obtained, which was recrystallized from acetone and had a melting point of 104.5-107°C.

In a 50 ml four-loop flask, add 2-7 minopyridyy0.
．． 942 g (10,0 mi IJ% jlz), 1.5 g (18,3 mmol) sodium carbonate and 15 acetone
Add mfL and add α-(3-trifluoromethylphenoxy)isoacetic acid chloride to 5 m of acetone from a separating funnel.
1 and dropwise over 5 minutes. After reacting by stirring at room temperature for 20 minutes, the reaction solution was heated and refluxed for 30 minutes. The reaction solution was returned to room temperature and filtered. When the acetone in the filtrate was distilled off, the desired N-(pyridin-2-yl)- α-(3-trifluoromethylphenoxy)isobutyric acid amide 3.20
g (99% yield) was obtained as an oil, 11 D1.52
It showed 37.

Examples of compounds of the general formula CI) according to the present invention are shown in Table 1.
However, it goes without saying that the compounds of the present invention are not limited to these examples, and many other compounds included in general formula (I) can be used as effectively as the specific example compounds. .

Note that the compound numbers are also referred to in the following examples and formulation examples.

In addition, in order to carry out the second agricultural and horticultural fungicide of the present invention,
The compound of the present invention of general formula CI) may be sprayed as it is on the foliage of cultivated crops, but in order to fully exhibit the bactericidal action of the compound of the present invention, it is necessary to combine the compound of the present invention with a suitable carrier and an auxiliary agent. Agent 1 For example, by mixing with a surfactant, a binder, a stabilizer, etc., a wettable powder, emulsion, aqueous solution, or
It is preferable to use it in the form of a formulation such as an oil suspension, granules, fine granules, or coarse powder.

The carrier used can be either solid or liquid, as long as it is commonly used for agricultural and horticultural chemicals.
Examples of solid carriers include, but are not limited to, mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium charcoal, apatite, white carbon, slaked lime, silica sand, sulfur, urea, etc.), vegetable powders (soybean, wheat flour, wood flour, tobacco powder, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl chloride, ketone resin, dammar gum, etc.) ), alumina, silicates, tM polymers, highly dispersed silicic acid, waxes, etc. Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, 1so-propyl alcohol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (benzene, toluene,
xylene, ethylbenzene, chlorobenzene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, monochlorobenzene, trichlorofluoromethane, dichlorodifluoromethane, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, isophorone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), ugly amides (dimethylformamide, dimethyl acetamide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane) Examples include industrial gasoline (petroleum ether, solvent naphtha, etc.) and petroleum fractions (paraffins, kerosene, light oil, etc.).

Furthermore, in the preparation of emulsions, wettable powders, flowable preparations, and the like, surfactants (or emulsifiers) are used for the purposes of emulsion dispersion, solubilization, wetting, foaming, lubrication, spreading, and the like. Such surfactants include nonionic types (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, nrubitan alkyl esters, etc.) and anionic types (alkylbenbensulfonates, alkylsulfosuccinates, etc.). esters, alkyl sulfates, polyoxyethylene alkyl sulfates, arylsulfonates, etc.),
Cationic types [alkylamines (laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.), polyoxyethylene alkylamines, etc.], amphoteric types [carboxylic acids (betaine type), sulfuric ester salts], etc. However, the invention is of course not limited to these examples.

In addition to these, various adjuvants such as polyvinyl alcohol, carboxymethyl cellulose, gum arabic, polyvinyl acetate, gelatin, casein, sodium alginate, and gum tragacanth can be used.

Furthermore, the compound of the present invention can be used in combination with other fungicides in order to improve the bactericidal efficacy or to expect a synergistic bactericidal effect. An example of this is cis-
N-(trichloromethylthio)-4-cyclohexene-
1,2-dicarpoxyimide, cis-N- (1,1,
2,2-tetra □ethylthio)-4-cyclohexene-1,2-dicarpoximide, tetrachloroisophthalonitrile, methyl-1-(butylcarbamoyl)
-2-benzimidazole carpamate, dimethyl-4
, 4''-0-phenylenebis(3-thioallophanate), 2-(4'-thiazolyl)-benzothiazole, L
-(4-chlorophenoxy)-3,3-dimethyl-1-
(IH-1,2,4-triazol-1-yl)-2-
Butanone, 1-(biphenyl-4-yloxy)-3,
3-dimethyl-1-(1,2,4-triazole)butanon-2-ol, zinc ethylene bisdithiocar octamate, tetramethylthiuram disulfide.

5-n-Butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, 6-methyl-1,3-dithiolo(4,5-b)quinoxalin-2-one, N-(3,
5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-poximide, 3-(3,5-dichlorophenyl)-5-ethynyl-5-methyl-2,4-
Oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-
Dioquin-1-imidazolidine carpoxamide, 5-methyl-1,2,4-triazolo(3,4-b)benzothiazole, 0.0-diinpropyl-3-benzylthiophosphate, 4.5,6. 7-tetrachlorophthalide, 3'-isopropoxy-2-methylbenzanilide, ? , 3-dichloroN-(4-fluorophenyl)
Maleimide, 5.10-dihydro-5,10-dioquinonenaphtho(2,3-b)-p-gutiine-2,3-dicarbonitrile, N'-dichlorofluoromethylthio-N
, N-dimethyl-N"-phenylsulfamide, manganese ethylene bisdithiocar/hemate, kasugamycin, validamycin, polyoxin, etc.
It is not limited to these.

In addition, the compound of the present invention may be used with an insecticide such as 0 or 1 if necessary.
．． 0-dimethyl S-(1,2-dicarpoethoxyethyl)phosphorodithioate, 2゜2-dichlorovinyldimethylphosphate, 02S-dimethyl N-7cetylphosphoroamidethiolate, 0,0-dimethyl 0-(
3-Methyl-4-nitrophenyl) phosphorothioate, 2-sec-butylphenyl N-methylcarbamate, 1-naphthyl N-methylcarbamate, S, S'
-(2-(dimethylamino)trimethylene)bis(thiocarbamate)hydrochloride, N-methyl-bis(
2,4-xylyliminomethyl)amine, hexakis(
A mixture of 2-methyl-2-phenylpropyl)-distannoxane, tricyclohexylhydroxystannane, and the like may be used.

Furthermore, the compound of the present invention can be used in combination with a herbicide, a plant growth regulator such as gibberellin, or a fertilizer, if necessary.

In the present invention, when manufacturing the various preparations described above, the compound of the present invention is contained in an amount of 0.1 to 95% (the same weight of 2 or less).
, preferably in the range of 0.5 to 90%.

For example, for regular powders, DL (driftless) powders, and fine granules (F), it is 0.1 to 5%, and for powders, it is 1 to 10%.
%, and in the case of aquariums, emulsions, and liquid preparations, it can be contained in the range of 5 to 95%.

The preparations prepared in this way are, for example, powders, DL powders,
In the case of fine granules (CF), it is enough to spray them directly on the stems of crops, and in the case of granules, they can be directly sprayed on the soil surface, in the soil, or in water at a dosage of about 2 to 5 kg per 1Oare (as the amount of active ingredients). (approximately 10 to 1,000 g), or in the case of emulsions, solutions, and wettable powders, dilute 500 to 2,000 times with water or an appropriate solvent, and add 5 to 1
1000 ppm, preferably about 50 to 500 ppm
This diluted solution is 100 to 300 per 10 ares.
f1. (10 to io as the amount of active ingredient.

It is sufficient to spray the foliage of crops in a range of about 0g).

Next, Examples of the formulation method of the present invention will be given, but the present invention is not limited to these Examples.

In addition, all parts in the examples mean parts by weight.

20 parts of compound No. 8, 3 parts of calcium polyoxyethylene alkylaryl ether sulfonate, and 172 parts of diatoms are uniformly mixed and pulverized to obtain a wettable powder containing 20% of the active ingredient.

1 Stand jLZ 1-1 20 parts of Compound No. 26, 60 parts of xylene and 20 parts of polyoxyethylene alkylaryl ether are uniformly dissolved and mixed to obtain an emulsion containing 20% of the active ingredient.

30 parts of Compound No. 58 and 70 parts of ethyl cellosolve are uniformly dissolved and mixed to obtain an oil solution containing 30% of the active ingredient.

1 shift 1'' Sol Flowable 10 = 40 parts of compound No. 21 crushed below,
2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of hydroxypropyl cellulose and 55 parts of water are evenly mixed to obtain a sol containing 40% of the active ingredient.

Wataru Shitane' Shiki-1 0.5 parts of compound No. 19, 0.5 parts of anhydrous silicon #fine powder.
5 parts of calcium stearate, 0.5 parts of calcium stearate, 50 parts of clay, and 48.5 parts of talc are uniformly mixed and ground to obtain a powder containing 1% of the active ingredient.

Length m grains - 3 parts of compound No. 65, 1 part of calcium lignosulfonate, 30 parts of bentonite and 66 parts of clay are uniformly mixed and pulverized, water is added and granulated, dried and sieved, Granules containing 3% of active ingredient are obtained.

C) fl Summer Death" Specific examples of the usefulness, action and effect of the compound of the general formula CI) of the present invention will be shown through test examples.

A predetermined concentration of a hydrating powder prepared according to Example 6 was sprayed on third leaf stage seedlings of paddy rice (variety: #J day) cultivated in soil using the bisque firing method and having a diameter of 9 cm in a greenhouse. After this - at night under greenhouse conditions (humidity 95-1.0%, temperature 24-25℃)
), and one day after the spraying, a spore suspension of the rice blast fungus was spray inoculated. Five days after inoculation, the number of rice blast lesions per third leaf was investigated, and the control value was calculated using a linear equation. In addition, chemical damage to rice was investigated using the following indicators.

The test is 1 concentration 3J1! The average control value was determined. The results are shown in Table 2. In addition, the investigation indicators for drug damage will be used in the same manner in the following test examples.

Investigation index for drug damage 5: Severe 2: Slight 4: Severe 1: Slightly 3: Many O: None
1 Kankyu 114, 200
72 015
200 7'5
0 other nenchi flea "Matabutsu" Gai ■1 Handuma ■5 engineering l Xuan Qiu trace 22 ZOO10002
520097, 0 39200, 970 Investigation boat No. 5 Ganbu crush' construction pressure 1 Takumi yoke 2 51 1 Xuanqiu 159 200 10
0. 060 200
too '0 kastopso 15 Kenyu' group bml ro l [0 sent IE hill genetic comparison drug A 200 due to drug damage 5
Comparative drug B that cannot be investigated 480 83
0 (compound described in German Published Patent Application No. 3101.889AI) Comparative Agent B A commercially available fungicide containing 020-diisopropyl S-benzyl phosphorothiolate (common name: IBP emulsion) was used.

The effect of controlling rice blast disease by low concentration treatment was investigated in the same manner as in Test Example 1 for rice blast using human liquid 1''. The results are shown in Table 3.

λyu1 -30Z
oo 100 9851
too 84 73 comparative drug B
23 5 0 untreated area
0 0 0 Representation 1' Rice Sesame-Paw, h A hydrating agent prepared according to Example 6 to seedlings at the fourth leaf stage of paddy rice (variety Niasahi) cultivated in clay pots with a diameter of 9 cm in a greenhouse. A chemical solution with a predetermined concentration was sprayed at a distance of 20 m per two pots. One day after the spraying, the plants were inoculated by spraying with a conidial suspension of the rice sesame leaf blight fungus, stored in a greenhouse at 24°C overnight, and then transferred to an infection greenhouse. Five days after inoculation with the disease fungus, the number of rice sesame leaf blight lesions per fourth leaf was investigated, and the control value (%) was calculated using the following formula.

(%) Average number of lesions per leaf in non-sprayed plots The results are shown in Table 4.

Plate soil barley Rice sesame presence Disease power - Mud W Abundance suppression 1 Inhalation I [Q method Mu■■8
200 too 0
Inclination υW Le 1 is Ωml pump old [0 trip l Harmful 5th comparison drug A 200 Due to drug damage
5 Comparative drug B that cannot be investigated 200 28
0 No spray area 0
- Set 0u balance port and place it in the bottom of a 7cm diameter plastic pot in advance.
A gold tooth agar disk (diameter 7 cm) of the sugar beet seedling blight bacteria cultured on DA medium was placed, and 100 g of field soil previously sterilized with chloropicrin was filled on top of the disk. This pot was cultured at 20° C. for 24 hours to allow mycelia to develop in the soil, and then a hydrating powder prepared according to Example 6 was diluted with water.

Each pot was irrigated with lomu. Thereafter, 10 sugar beet seeds were sown per 7 pots and stored in a thermostat at 20°C to promote disease onset. The disease state was investigated 14 days after sowing, and the healthy seedling rate (%) was calculated using the following formula.

The results are shown in Table 5.

Chopsticks mutual life sugar beet - standing defense - 1L Ikushi series kml Wa Ren Koju Gen ■Iku 4
, 1000 80
08 1000
too 038 1000
too 069
1000 too
0 Comparative drug A 1000 Due to drug damage 5 Comparative drug C1000955 Bacterial inoculation untreated group -〇 - No inoculated untreated group -ioo - Comparative drug C is
A commercially available hydrating powder containing 50% pentachloronitrobenzene (PCNB) was used.

Patent Applicant: Hokuko Chemical Industry Co., Ltd. Procedural Amendment Date of June 1985

Claims (1)

[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R is a lower alkyl group, a halogen atom, CF_3
group, NO_2 group, lower alkoxy group, n is 0 to 3
Het is a pyridine ring substituted or unsubstituted with a group selected from a lower alkyl group, a halogen atom, an NO_2 group and a lower alkoxy group,
A phenoxyisobutyric acid amide derivative represented by a pyrimidine ring, an isoxazole ring, an isothiazole ring, a thiadiazole ring or a quinoline ring. 2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R is a lower alkyl group, a halogen atom, CF_3
group, NO_2 group, lower alkoxy group, n is 0 to 3
Het represents a pyridine ring, pyrimidine ring, isoxazole ring, isothiazole ring, thiadiazole ring or quinoline ring substituted or unsubstituted with a group selected from lower alkyl groups, halogen atoms, NO_2 groups. An agricultural and horticultural fungicide characterized by containing a phenoxyisobutyric acid amide derivative represented by the following as an active ingredient.