JPS58150590A - Novel n,n'-substituted azolecarboxamide derivative and agricultural and horticultural fungicide containing it as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formulaI(R1 is H, methyl, or ethyl; R2 is lower alkyl; X and Y are C or N, with the proviso that Y is C or N when X is N, and Y is N when X is C). EXAMPLE:N-( 1-Ethoxycarbonylethyl )-N-( 2-furfuryl )-imidazole-1-carboxyamide shown by the formula II. USE:An agricultural and horticultural fungicide. PROCESS:A carbamoyl halide shown by the formula III (Hal is halogen) is reacted with an azole shown by the formula IV in an inert solvent at 0 deg.C- the reflux temperature at the boiling point of the solvent for about 10min-several hours, to give a compound shown by the formulaI. A hydrogen halide evolved during the reaction is preferably trapped with a tertiary amine (e.g., triethylamine, pyridine, etc.) or excess azole shown by the formula IV.

Description

[Detailed description of the invention] (In the formula, & represents a hydrogen atom, a methyl group or an ethyl group,
R2 represents a lower alkyl group, and X and Y each represent a carbon atom or a nitrogen atom.

However, when X is a nitrogen atom, Y represents a nitrogen atom or a carbon atom, and when X is a carbon atom, Y represents a nitrogen atom. )
The present invention relates to an agricultural and horticultural fungicide containing a novel N,N'-substituted azole carboxamide derivative represented by (hereinafter abbreviated as "the compound of the present invention") and one or more thereof as an active ingredient.

Conventionally, it has been used as a control agent for agricultural and horticultural crop diseases.

There are organic chlorine agents, organic sulfur agents, gas agents, etc.

Organic chlorine agents tend to cause phytotoxicity, and do not have a control effect unless they are treated at high concentrations.
Organic sulfur agents tend to cause drug damage and may cause skin irritation, while gas agents have drawbacks such as having a pungent or unpleasant odor.

The present inventors have discovered that a novel compound represented by the formula (Il) exhibits a wide range of control effects without taking into account the drawbacks of conventional fungicides, and does not have any adverse effects on plants, such as phytotoxicity. was completed.

The compound of the present invention is produced by the following method (A) or (B).

(3) Formula (wherein R□ and R2 are the same as in formula (I).
indicates a halogen atom. ) A carbamoyl halide represented by the formula (wherein,
A compound of the present invention can be obtained by carrying out a reaction for several hours. The hydrogen halides generated during the reaction are tertiary amines (
For example, triethylamine.

It is preferable to use an excess of the azole represented by formula (III) such as pyridine.

(In the formula, X and y rA"i (I) are the same.) Carbonylbisazole represented by the formula (In the formula, + R1 and R2 are the same as the formula (Il).) The compound of the present invention can be obtained by reacting in an inert solvent at oC to the boiling point reflux temperature of the solvent for about 10 minutes to several hours.

The inert solvent in the above production process is aliphatic and aromatic optionally chlorinated carbon (L hydrogens, eg everbenzene, toluene, xylene).

Examples include chlorobenzene, methylene chloride, 1,1,1-trichloroethane, chloroform, carbon tetrachloride, etc., and ethers such as diethyl ether-dioxane and tetranohydrofuran.

The carbamoylnolide represented by formula 1 is a combination of secondary amines represented by 2M and carbonyl halide represented by formula (Vl) or formula (■) (in the formula, 11 Hal is the same as in formula I). and oC in an inert solvent
It is obtained by reacting for about 10 minutes to several hours at the boiling point reflux temperature of the solvent.

The carbonylbisazole represented by the formula (IV) is a combination of an azole represented by the formula (m) and a carbonyl halide represented by the formula (■ or formula (■)) in the inert solvent at OC to the boiling point and reflux temperature of the solvent. The reaction is advantageously carried out in the presence of a suitable acid binder such as triethylamine or tertiary amines such as pyridine.

An example of the carbonylno-ride represented by formula (Vl) is preferably phosgene, and an example of the carbonyl halide represented by formula (■) is preferably trichloromethyl chloroformate. These compounds are created by known synthetic methods, and a specific example is imidazole.

Examples include pyrazoles and triazoles. Further, the secondary amines represented by formula M are produced by the following known synthesis method.

(wherein +Ft, and R2 are in formula (I), and Hat
is the same as equation 0. ) is obtained by reacting a halogenated carboxylic acid nystere represented by the following formula with furfurylamine.

The lower alkyl group represented by R2 in formula (Il) includes groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and secondary butyl.

(Represented by HaJ in formula 0) - Examples of the rogene atom include a chlorine atom and a bromine atom.

Typical compounds of the present invention produced as described above are shown in Table 1.

Table 1 N,N'-Substituted Azole Carboxamide Derivatives Next, the method for producing the compounds of the present invention will be illustrated in more detail with reference to the following Examples.

Example 1. N-(1-ethoxycarbonylethyl)-N
-(2-Furfuryl)-imidazole-1-carboxamide (N12) (Method B) Trichloromethylchloroformate LOy-(0,05
mol) dissolved in dry tetrahydrofuran 100mA!
In it, imidazole l 3.6 Sl- (0.2 mol) and triethylamine 10. 100++ l of a dry tetrahydrofuran solution containing I P (0.1 mol) at OC~10
Drop while keeping the temperature at C. After stirring for about 1 hour -N-(1-
40 ml of a dry tetrahydrofuran solution containing 19.7 fi (0.1 mol) of (ethoxycarbonylethyl)-N-2-furfurylamine is gradually added dropwise while maintaining the temperature between 5C and 10C. After that, it was refluxed for 1 hour, cooled to room temperature, poured into water, extracted with ethyl acetate, washed with water, separated, dehydrated,
After a conventional concentration process, the product was purified by silica gel column chromatography to obtain 16@(0,055 mol) of an oily substance.

The physical constants of the above compound N2 are as follows.

Infrared absorption spectrum (KBr tablet): 1700cm
-' (C=0 stretching, amide absorption), 174 ocn
r'< c=o stretching, ester absorption) Proton signal 7.01) pm (s, IH), 6.35 ppm (s
, 2I()-furan ring proton signal Example 2. N-(ethoxycarbonylmethyl)-N-(
2-furfuryl)-triazole-1-carboxamide (1'1&14) N-(1-ethoxycarbonyl) was added to a solution containing 100 mJ of dry tetrahydrofuran and 10F-(0, osmol) of trichloromethylchloroformate under cooling at OC to 5C. methyl)-N-2-furfurylamine 13i (0,07
30ml of dry tetrahydrofuran solution containing 1 mol)
Drip 1. The mixture is then stirred at room temperature for 300' and a solution of 9.85' (0.121 mol) of triazole in 200 ml of dry tetrahydrofuran is added at 10C-15C'. Thereafter, the mixture is gradually heated and reacted under reflux for about 1 hour. After cooling at room temperature 1, pour into water, perform extraction with ethyl acetate, wash with water, separate and dehydrate in the usual manner, concentrate the ethyl acetate layer, and purify the residue by silica gel chromatography to obtain 13P(0, 0468 mol) of an oil is obtained.

The physical constants of the above compound Nn4 are as follows.

Infrared absorption spectrum (KBr tablet): 1700z-'
(C=0 stretching, amide absorption) -1740z (C=0
stretching, ester absorption) NMR, spectrum (CDC13): 8.91) pm
(s, IH) -7,95 ppm (S, IH)...triazole ring proton signal, 7.4 ppm (s, I
H) -6,4ppm (a, 2H piece-7 run ring proton signal reference example t N -(1-ethoxycarbonylethyl)
-furfurylaminefurfurylamine19.451-(
0.2 mol) and α-bromopropionic acid ester 18.
17 (0.1 mol) was added dropwise while cooling with ice water while maintaining the temperature at io' to 20C. After stirring overnight at room temperature, it is poured into water and the resulting oil is extracted with 100 Fnl of ethyl acetate.

After washing the ethyl acetate layer with water and drying with anhydrous sodium sulfate,
By concentrating and performing vacuum distillation, 1627 (0,08
2 mol) of an oil are obtained. Boiling point is 120C to 125C
/ 3 mmHg (colorless and transparent liquid).

When the compound of the present invention is used as a fungicide for agriculture and horticulture, depending on the purpose of use, it is generally used in the field of agrochemical manufacturing, in which a pesticide adjuvant is used to enhance or stabilize the effect. It can be used in the production form of powders, fine granules, granules, irrigation agents, flowable preparations, emulsions, etc. by the method described above.

These various formulations are used in actual use.

It can be used directly or diluted with water to the desired concentration.

The agrochemical auxiliaries mentioned here include carriers (diluents) and other auxiliaries such as spreading agents and emulsifiers.

Wetting agents - dispersing agents, fixing agents, disintegrants, etc. can be mentioned.

Liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and methylnaphthalene.

Examples include cyclohexane, animal and vegetable oils, fatty acids, and fatty acid esters.

Solid carriers include clay, kaolin, and talc.

Diatomaceous earth, silica, calcium carbonate, montmorillonite,
Examples include bentonite, feldspar, quartz, alumina, and sawdust.

Surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. , nonionic surfactant 1 and amphoteric ionic surfactant.

All formulations can not only be used alone, but may also be mixed with fungicides, insecticides, plant growth regulators, acaricides, herbicides, soil fungicides, soil conditioners, or nematicides. Furthermore, it can be used in combination with fertilizers and other agricultural and horticultural fungicides.

The active ingredient compound content in the agricultural and horticultural fungicide of the present invention is:
It varies depending on the formulation form, method of application, and other conditions, and in some cases only the active ingredient compound may be used.
Usually 0.5 to 95% (weight), light and heavy, 2 to 70% (by weight)
weight).

When actually using the agricultural and horticultural fungicide of the present invention, it is best to apply it as a foliage spray at a concentration of 10 to 4,000 ppm, and as a soil spray, the compound of the present invention should be applied at a concentration of 0.05 kg to 10 are. It is appropriate to apply 10 kg.

Next, the agricultural and horticultural fungicide of the present invention will be explained in more detail using specific examples, but the type and mixing ratio of the agricultural chemical auxiliary agent are not limited to these, and can be used in a wide range. Note that "parts" means "parts by weight."

Powder Example 1, Powder Compound r11[1t(N-(1-ethoxycarbonylmethyl)-N-(2-furfuryl)-imitasol-
10 parts of l-carboxamide), 41 parts of talc, and 49 parts of clay were mixed and ground to form a powder.

Formulation example 2. Irrigation agent (f4 product rb 2 (N-(1-ethoxycarbonylethyl)-N-(2-furfuryl)-imidazole-1
- 80 parts of carboxamide), 15 parts of kaolin, 3 parts of sodium higher alkyl sulfate, and 2 parts of sodium polyacrylate are mixed in a powder ratio to prepare an irrigation agent.

Formulation example 30 grains Compound rk5 (N-(1-ethoxycarbonylethyl)-N-(2-furfuryl)-triazole-1-carboxamide) 3 parts, diatom ±35 parts, bentonite 23
1 part of water, 37 parts of talc, and 2 parts of disintegrant.
8 parts were added, moistened evenly, first extruded through an injection molding machine, granulated, dried, passed through a crusher, and then sized with a sieve to a particle size of 0.6 yxtx to 1 x m. Take the form of granules.

Formulation Example 4 parts Microgranules Compound Th13 (N-(1-ethoxycarbonylethyl)-N-(2-furfuryl)-imidazole-1-carboxamide) 5 parts and bentonite 6 parts.

Mix and grind evenly with 9 parts of clay to form a thick powder. Separately, 80 parts of non-oil-absorbing mineral coarse powder of 105 .mu.m to 74 .mu.m was placed in a suitable mixer, and 20 parts of water was added thereto while making one rotation to moisten it, and the above-mentioned thick powder was added thereto.

Coat and dry to form fine granules.

Formulation example 5. Emulsion compound 1'h2 (N-(1-ethoxycarbonylethyl)-N-(2-furfuryl)-imidazole-1
- 20 parts of carboxamide) are dissolved in 63 parts of xylene,
To this was added a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (8:2
) are mixed and dissolved to form an emulsion.

Next, it will be explained using experimental examples that the active ingredient compound of the present invention has excellent control effects against a wide range of agricultural and horticultural crop diseases.

Experimental example 1. Cucumber powdery mildew control test The emulsion containing the compound of the present invention as an active ingredient prepared in Example 5 was diluted with water and applied to potted cucumbers (cultivar 2F1 strong kagreen nodules) in the stage of first true leaf development. After spraying and air-drying, the cucumber powdery mildew fungus (5phaeroihecaful 1g1nea
) was inoculated and placed in a greenhouse, and two weeks later, the degree of disease onset was investigated and the control value was calculated. Thiophanate methyl 70% water conservancy (active ingredient: 1,2-bis(
3-methoxycarbonyl-2-thioureido)benzene) was used. The results are shown in Table 2. The disease index and control value were calculated as follows.

A: Number of stocks with severe disease B: Number of stocks with severe disease C: Number of stocks with slight disease D: Number of healthy stocks Experimental example 2. The emulsion containing the compound of the present invention prepared in Preparation Example 5 for controlling cucumber scabrous blight is diluted with water and sprayed on cucumber (variety: Tokiwa Jizoi) at the first true leaf stage. Clado
A spore suspension of Sporium cucumerinum was spray inoculated, kept in a greenhouse at 20C for one day, and then allowed to develop in the greenhouse. Seven days after inoculation, the degree of disease onset was investigated and the control value was calculated.

The results are shown in Table 3. The disease index and control value were calculated as follows.

Disease index - 19.9''''''Wangdany99n'-!−'−
x 1o.

(AfB10C+D) An emulsion containing the compound of the present invention was diluted with water and sprayed on primary leaves of common beans (variety: Shin-Edo). After air-drying, mycelia of Botrytis cinerea were punched out with a cork pole with a diameter of 5 mm. The pieces were left to stand and kept in a greenhouse to allow the disease to develop, and 48 hours later, the lesion diameter was examined and the control value was calculated. Benomyl 50% aqueous agent (active ingredient: methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate) was used as a control drug. The results are shown in Table 4. The control value was calculated as follows.

Table 4 Experimental Example 4. Cucumber seedling damping-off control test 12crn A clay pot is filled with field soil IK, and on top of this, seedling damping-off fungus (Rh
1zoctonia 5olani) was uniformly inoculated onto the soil surface. Then add 1 cucumber seed (variety: F11 strong turnip) per pot.
0 seeds were sown, and 50 m of a chemical solution prepared by diluting the emulsion containing the compound of the present invention prepared in Formulation Example 5 with water was added per pot.
1 irrigation. Infection was carried out in a greenhouse. Cabtan 80% irrigation agent (active ingredient: N-t+f chloromethylthiotetrahydrophthalimide) was used as a control drug. Sowing 1
After 0 days, the disease state was investigated and the healthy seedling rate was calculated. The results are shown in Table 5. The healthy seedling rate is calculated as follows.

Table 5 Patent Applicant Nippon Kayaku Co., Ltd. Continued from page 1 307100 7043-4 C2491
00) 7132-4C@Inventor
Kengo Koike 493-3 Jitogata, Ageo City 0 Inventor Shizuo Shimano 2-11-23 Kamimachi, Ageo City @ Inventor 606 Koshikitani, Nakayo Taisumi Ageo City ■・Inventor Kaoru Omori 943-133 Shimohideya, Okegawa City Procedures Amendment May 13, 1980 Commissioner of the Japan Patent Office Shima 1) Spring tree l Case indication 1982 Patent Application No. 33040 No. 2-1 Marunouchi-chome, Chiyoda-ku, Tokyo (408) Representative of Nippon Kayaku Co., Ltd. Person President Tsunekazu Sakano 5 Date of supplementary order (voluntary) b Number of inventions increased by amendment None 7 Amendments
Subject: Supplement to the “Detailed Description of the Invention” column in the specification
Correct content 1: “Wilting disease, etc.” in the specification, page 3, line 5 from the bottom
It says, ``Wild wilt, rice blast, and sesame leaf blight.

Corrected to ``Tsuruwari disease, etc.''.

2, same, page 8, Table 1, the following table with the following data is added to the column of melting point or refractive index and appearance of compounds 6, 7 and 8.

4 rKBrJ in the same place as ``rKBr tablet''
Correct.

(II, page 10, first line.

(2) Page 11, line 8.

5 Same, page 11, lines 6 to 5 from the bottom, “Reference example 1
...Furfurylamine 19.4 P (0.2 J,
Correct t-+ru as follows.

1 [Example 1. Synthesis of N-(1-ethoxycarbonylethyl)-furfurylamine.

Furfurylamine t9.4y (o2) 6, same page, 3rd line from the bottom, "lOo" is r
lc) Correct C).

7. Ibid., p. 14, line 8, ``When actually using,
``Stems and leaves'' are sprayed on foliage or soil and have excellent control effects against crop diseases by either method of application, but in particular, it is effective against above-ground diseases such as powdery mildew, scab, etc. It has a premature control effect against gray mold, etc.Then, it has been corrected to ``Stems and leaves''.

8 Same, page 15, line 8, it says "mixed powder ratio".
Corrected to "mixed crushing".

9. Ibid., page 16, the first line "imidazole" is corrected to "pyrazole."

10, ibid., page 21, the following text and table are added after table 5.

"Experimental Example 5. Cucumber Powdery Mildew Control Test by Soil Application 1 An emulsion containing the compound of the present invention prepared in Formulation Example 5 was applied to cucumbers (cultivar: Tokiwa Jizoui) at the first true leaf stage grown in 1Ocrn pots. 25 ml of the chemical solution diluted with water was applied to the soil per pot.
) inoculated with spores.

The degree of disease onset was investigated after 2 weeks after being placed in a greenhouse.

The control value was calculated. Dumethylimole 12 as a control drug
．． A 5% solution (active ingredient: 5-butyl-2-dimethylamine-6-methylpyrimidin-4-ol) was used. The results are shown in Table 6. The criteria for the degree of disease onset and the method for calculating the control value were in accordance with Experimental Example 1.

Table 6 Experimental Example 6. Cucumber scabosis control test by soil application 10crn A chemical solution prepared by diluting with water an irrigation agent containing the compound of the present invention prepared in Formulation Example 2 on cucumbers (cultivar: Tokiwa Jizoi) grown in pots at the first true leaf stage. was applied to 25 m of soil per pot. Cladosporium cucumerinum
) was spray inoculated with a spore suspension and kept in a greenhouse at 20°C for 1 day.

The disease was caused to develop in a greenhouse, and the degree of disease onset was investigated 7 days after inoculation, and the control value was calculated. Criteria for severity of disease onset.

Experiment 1 One cucumber at the first true leaf stage (cultivar: 2F1 strong kagreen) grown in an Ocrn pot was treated with 1 dose of the emulsion containing the compound of the present invention prepared in Formulation Example 5 diluted with water.
25 ml of soil was applied per pot. Three days later, a mycelial piece of Botrytis cinerea punched out with a cork pole with a diameter of 5 mm was placed on the first true leaf and kept in a greenhouse to allow the disease to develop. After 48 hours, the lesion diameter was examined. The control value was calculated. The results are shown in Table 8. The method for calculating the control value was in accordance with Experimental Example 3.

Table 8 Experimental Example 8. 5 Tests for Controlling Kiucumber Vine Disease] Field soil was packed in a 2Cr pot, and then on top
Sarium oxysporum (, Sp+cuc
umerinum) tl cultured pathogenic soil was uniformly inoculated onto the soil surface. Thereafter, 10 seeds of Ki= and Cucurbita (variety 2F6 strong green joints) were sown per pot, and a chemical solution prepared by diluting the emulsion containing the compound of the present invention prepared in Formulation Example 5 with water was added per pot. 50ml was irrigated. Infection was carried out in a greenhouse. As a control drug, Benomy Kokuru 50% water conservancy (active ingredient 2-methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate) was used. Ten days after sowing, the disease state was investigated and the percentage of healthy seedlings was calculated. The results are shown in Table 9. The method for calculating the healthy seedling rate was in accordance with Experimental Example 4.

Experimental example 9. Mandarin orange storage disease control test Mandarin fruit was immersed in a chemical solution prepared by diluting the emulsion containing the compound of the present invention prepared in Formulation Example 5 with water, air-dried, and then scratched with a needle.
talicum) was spray-inoculated and kept in a greenhouse to induce disease.

Thiophanate methyl 70% aqueous solution (active ingredient = 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene) was used as a control drug. The results are shown in Table 10.

Experimental example 10. Antibacterial activity test An agar plate containing a prescribed concentration of the drug was prepared by the agar plate dilution method using a potato agar medium, and the test bacteria shown in Table 11 was inoculated onto it, and after culturing for 5 days at 25C, the minimum growth inhibitory concentration ( MIC) 7 was obtained. The results are shown in Table 11.

Table 11 The numbers in Table 1 are MIC (mc'g/ml).

A value of 50 or less indicates strong antibacterial activity, a value of 50 to 250 indicates somewhat strong antibacterial activity, and a value of 250 to 500 indicates moderate antibacterial activity.

Experimental example 11. Antibacterial activity test Agar plates containing the drug at a predetermined concentration were prepared using the agar plate dilution method using potato agar medium.

The test bacteria were inoculated thereon, and after culturing for 5 days at 25C, the minimum inhibitory concentration (MIC) of the bacteria was determined. Verti as a test bacterium
cillium albo-a! I used rum.

knee/ The results are shown in Table 12.

Procedural amendment filed in July 1980 by the Commissioner of the Japan Patent Office Kazuo Sugi 1 Display of case Patent Application No. 53040 of 1983 Representative Tsunekazu Sakano, President and CEO 6 Number of inventions to be increased from amendment meeting None 7 Subject of amendment Amendment to the “Detailed Description of the Invention” column of the specification
Contents 1. Procedural amendment to the description (dated May 13, 1988)
The table in paragraph 3 on page 1 of ``Contents of Amendment'' is amended and added as follows.

2. In the same article, page 2, line 9 from the bottom, ``soil application j'' should be corrected to ``soil application.''

3. On the same page, in the 8th line from the bottom, the words "spraying method" should be corrected to "1 application method."

4. Experimental Example 5 on page 3 of the same is corrected as follows.

[Experiment Example 5 Cucumber powdery mildew control test by soil application Cucumbers grown in 10 cm pots at the first true leaf development stage (
A chemical solution prepared by diluting the emulsion containing the compound of the present invention prepared in Formulation Example 5 with water was applied to the soil (variety: Tokiwa Jirai) at 25 ffi per pot. After 3 days, cucumber powdery mildew fungus (Sphaerothecafuliginea)
) was inoculated and placed in a greenhouse, and two weeks later, the degree of disease onset was investigated and the control value was calculated.

The results are shown in Table 6.

The criteria for the degree of disease onset and the method for calculating the control value were in accordance with Experimental Example 1.

"Table 6" 5, same page, page 4, the last line "Calculated. Severity of disease onset" is [Calculated. The results are shown in Table 7. Degree of onset of illness”
Correct.

6. The same, page 5, table 7 is amended as follows.

[Table 7 7. Same, page 6, table 8 is amended as follows.

"Table 8" 9, same, page 7, in the third line from the bottom, correct "J in the greenhouse" to "in the greenhouse."

10. Same, page 8, in the second line from the bottom, the phrase "minimum growth after cultivation" is corrected to "minimum growth of bacteria after cultivation."

11, same, page 9, at the end of the page, the phrase "minimum inhibitory concentration for bacteria" is corrected to "minimum inhibitory concentration for bacteria."

that's all

Claims (1)

[Claims] (In the formula, Rt is a hydrogen atom-methyl group or ethyl group,
R2 represents a lower alkyl group, and X and Y each represent a carbon atom or a nitrogen atom; however, when X is a nitrogen atom, Y represents a nitrogen atom or a carbon atom, and when X is a carbon atom, Y indicates a nitrogen atom. ) A novel N,N'-substituted azolecar represented by (wherein Rs is a hydrogen atom, a methyl group or an ethyl group,
2 represents a lower alkyl group, and X and Y each represent a carbon atom or a nitrogen atom, however, when X is a nitrogen atom, Y represents a nitrogen atom or a carbon atom, and when X is a carbon atom, Y represents a nitrogen atom. Indicates an atom. ) is the new N expressed by
, N'-substituted azole carboxamide derivatives as an active ingredient.