JP2019196310A - Insecticidal, miticidal, nematicidal, molluscicidal, germicidal or bactericidal composition, and method of controlling pest - Google Patents

Abstract

To provide novel insecticidal, miticidal, nematicidal, molluscicidal, or germicidal composition.SOLUTION: There is provided a novel insecticidal, miticidal, nematicidal, molluscicidal, or germicidal composition containing one or two kind of active compound I selected from a condensed heterocyclic compound represented by the formula (1), a salt thereof or N-oxide thereof, and one or two kind of active compound II selected from known insecticide. Q is Q1 or Q3, Ais Cto Calkyl, Aand Aare each independently N or the like, Ris Cto Calkyl, Ris halo(Cto C)alkyl or the like, Rand Rare H, Y2 to Y4 are each independently H, a halogen atom, or the like, and n is an integer of 0 to 2.SELECTED DRAWING: None

Description

  The present invention relates to a fused heterocyclic compound represented by the specific formula (1) and an active ingredient compound of a known insecticide, acaricide, nematicide, molluscicide, fungicide or bactericide. It is related with the pest control agent characterized by mixing.

  The condensed heterocyclic compound represented by the formula (1) (hereinafter abbreviated as “compound (1)”), which is the first active ingredient compound in the composition of the present invention, is a known compound and its pest control. The activity is known as an agent (for example, refer to Patent Document 1).

  In addition, compounds having insecticidal activity, acaricidal activity, nematicidal activity, molluscicidal activity, bactericidal activity or bactericidal activity, which are the second active ingredient compounds in the composition of the present invention, are all known (for example, Non-patent document 1).

International Publication No. 2016/129684

The Pesticide Manual, 16th edition, The British Crop Protection Council, 2012

  Today, the development of insecticides, acaricides and fungicides for the control of various pests such as agricultural and horticultural pests, forest pests, and hygiene pests is widely promoted, and a wide variety of drugs are put into practical use. However, in recent years, as a result of the long-term use of such drugs, pests have acquired insecticide resistance, and pathogens have acquired fungicide resistance. As a result, there are increasing situations in which it is difficult to control with conventional drugs. Some of these drugs are highly toxic and some are perturbing the ecosystem by remaining in the environment for a long time. Therefore, development of a novel drug that not only has a high pest control effect but also has low toxicity and low environmental persistence is always expected.

  On the other hand, considering the diversity of pests and pathogens as a group of organisms, the mode of harm, and the variety of harm scenes, the use of these new drugs or existing known drugs alone is all in all control situations. It is very difficult to control the pests effectively. Therefore, a new combination of multiple insecticides, acaricides, nematicides, molluscicides, fungicides, or bactericides to induce higher control efficacy and control difficult pests. A method has also been strongly desired.

  In view of such circumstances, the present inventors have conducted intensive research to develop a pest control agent that exhibits excellent pest control activity and has less adverse effects on non-target organisms such as mammals, fish, natural enemies, and beneficial insects. As a result, a composition containing the compound (1) and a certain known insecticidal, acaricidal, nematicidal, molluscicidal, compound having bactericidal or bactericidal activity is used alone. The present invention has been found to have an excellent synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect that cannot be predicted from the present invention.

  That is, the present invention relates to the following compositions [1] to [3] (hereinafter referred to as the present composition) and the control methods [4] to [7] (hereinafter referred to as the present method). Is.

[1]
An insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal composition comprising a synergistically effective amount of at least two active compounds,
1) One or two active compounds I are of the formula (1):

[Wherein Q represents a ring represented by either Q1 or Q3;

A ^1a represents C ₁ -C ₆ alkyl,
A ⁴ represents a nitrogen atom or C (R ⁴ ),
A ⁵ represents a nitrogen atom or C (R ⁵ ),
R ¹ represents C ₁ -C ₆ alkyl;
R ³ represents halo (C ₁ -C ₆ ) alkyl, halo (C ₁ -C ₆ ) alkylthio, halo (C ₁ -C ₆ ) alkylsulfinyl or halo (C ₁ -C ₆ ) alkylsulfonyl;
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
Y2, Y3 and Y4 each independently represent a hydrogen atom, a halogen atom, a halo _(C 1 _{~C 6)} alkyl or cyano,
n represents an integer of 0, 1 or 2. A fused heterocyclic compound represented by the formula:
2) One or more active compounds II are the following active ingredient groups BI to B-XXVI:
Active ingredient group BI: metalaxyl-M and hymexazol.

  Active ingredient group B-II: benomyl, thiophanate-methyl, diethofencarb, ethaboxam, zoxamide, pencycuron and fluopicolide.

  Active ingredient group B-III: benzovindiflupyr (benzovindiflupyr), bixafen (boscalid), boscalid (boscalid), fluindapyr (fluindapyr), fluopyram (fluopyram), flutolanil (flutolanil), fluxapiroxad (fluxapyroxad), flametopyr ( furametpyr), isoflucipram (isoflucypram), inpyrfluxam, isofetamid, isopyrazam, mepronil, penflufen, penthiopyrad, sedaxane, flu thifluzamide, azoxystrobin, coumoxystrobin, dimoxystrobin, enestrobin, enoxastrobin, famoxadone, fenamidon e), phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, orisatrobin (Orysastrobin), picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb-methyl, pyriminostrobin ), Triclopyricab, trifloxystrobin, amisulbrom, cyazofamid, fluazinam, fenpicoxamid, ametoctrazine, ametoctradin Flumethofen and pyraziflumid.

Active ingredient group B-IV: mepanipyrim and kasugamycin
Active ingredient group BV: quinoxyfen and fludioxonil.

  Active ingredient group B-VI: iprodione and procymidone.

  Active ingredient group B-VII: tolclofos-methyl and Bacillus subtilis (Strain: D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.).

  Active ingredient group B-VIII: bromuconazole, cyproconazole, difenoconazole, diniconazole-M (diniconazole-M), epoxiconazole, fenarimol, fenbuconazole (Fenbuconazole), fluquinconazole, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, penconazole Prochloraz, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triflumizole Fenpropidin (fenpropidin), fenhexamid (fenhexamid), Fenpirazamin (fenpyrazamine), type phen triflupromazine Kona tetrazole (ipfentrifluconazole) and main phen triflupromazine Kona tetrazole (mefentrifluconazole).

  Active ingredient group B-IX: validamycin, polyoxins, polyoxin-D (polyoxorim), benchthiavalicarb-isopropyl, dimethomorph, iprovalicarb and mandipropamid .

  Active ingredient group B-X: phthalide, tricyclazole, carpropamid, and diclocymet.

  Active ingredient group B-XI: acibenzolar-S-methyl, probenazole, isotianil, dichlobentiazox and thiadinyl.

  Active ingredient group B-XII: Bordeaux mixture, basic copper carbonate (copper carbonate, basic), cupric hydroxide (copper hydroxide), copper naphthenate (copper naphthenate), copper oleate (copper oleate), Basic copper chloride, copper sulfate, copper sulfate, basic, oxine copper, calcium polysulfide, sulfur, mancozeb (Mancozeb), maneb, polycarbamate, propineb, captan, folpet, chlorothalonil, iminoctadine-albesilate and iminoctadine acetate (Iminoctadine-triacetate).

  Active ingredient group B-XIII: aminopyrifen, cyflufenamid, cymoxanil, flusulfamide, flutianil, fosetyl-aluminium, metrafenone, oxathia Oxathiapiprolin, pyriofenone, picarbutrazox, dipymetitrone, quinofumelin, lipopeptide (Lipopeptide), phosphorous acid, BCF-082 (test name) NF-180 (test name), S-2399 (test name), AKD-5195 (test name) and S-2190 (test name).

  Active ingredient group B-XIV: Acephate, Cadusafos, Chlorpyrifos, Diazinon, Dichlorvos, Dimethoate, EPN, Malathionet, hamidophos ), Parathion-methyl, Phenthoate, Phorate, Phosmet, Phoxim, Profenofos and Terbufos.

  Active ingredient group B-XV: Aldicarb, Benfuracarb, Carbaryl, Carbofuran, Carbosulfan, Methomyl, Pirimicarb and Thiodicarb.

  Active ingredient group B-XVI: Acrinathrin, bifenthrin, cyfluthrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, permethrin ), Tefluthrin, lambda-Cyhalothrin and tau-Fluvalinate.

  Active ingredient group B-XVII: Bensultap, Cartap hydrochloride, and Thiocyclam.

  Active ingredient group B-XVIII: Acetamiprid, clothianidin, Dinotefuran, flupirimin, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam, thiamethoxam ), Flupyradifurone, Triflumezopyrim and Dicloromezotiaz.

Active ingredient group B-XIX: Spinetoram and Spinosad
Active ingredient group B-XX: Ethiprole, fipronil and broflanilide.

  Active ingredient group B-XXI: Abamectin, Emamectin benzoate, Lepimectin, and Milbemectin.

  Active ingredient group B-XXII: Chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetratraniliprole and cyhalodiamide.

  Active ingredient group B-XXIII: Diafenthiuron, Fenpyroximate, Pyridaben, Tolfenpyrad, Cyenopyrafen, Cyflumetofen, Pydrabumnon, Pydrabumnon ), Acequinocyl and chlorfenapyr.

  Active ingredient group B-XXIV: benzpyrimoxan, pyriproxyfen, methoxyphenozide, diflubenzuron, flufenoxuron, lufenuron, novaluron, tefluben (Teflubenzuron), Buprofezin, Hexythiazox and Etoxazole.

  Active ingredient group B-XXV: Bacillus thuringensis and Bacillus sphaericus.

Active ingredient group B-XXVI: Acinonapyr (acynonapyr), Pymetrozine, Pyrifluquinazon, Aphidopyropen, Flonicamid, Spirodiclofen, Spiromesifen, Spiromesifen, Spiromesifen , Spirotetramat, Indoxacarb, Metaflumizone, Cyromazine, Azadirachtin, Pyridalyl, Bifenazate, Fluxametamide, Metaaldehyde Metaldehyde), ME-5382 (test name), NA-89 (test name), NNI-1501 (test name), BAI-1602 (test name), DKN-2601 (test name) and DAI-1601 (test name) .
Said insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal composition which is a compound selected from.

[2]
Q represents a ring represented by Q1,
A ⁴ represents C (R ⁴ ),
A ⁵ represents a nitrogen atom,
R ³ represents halo (C ₁ -C ₆ ) alkyl or halo (C ₁ -C ₆ ) alkylsulfinyl,
Y2 and Y3 represent each independently a hydrogen atom, a halogen atom or a halo _(C 1 _{~C 6)} alkyl,
Y4 represents a hydrogen atom, a halogen atom or cyano,
n represents an integer of 2, the insecticidal, acaricidal, nematicidal, bactericidal or bactericidal composition according to [1] above.

[3]
Acetamiprid, clothianidin, imidacloprid, thiamethoxam, suloxafurol, spinetoram, emamectin benzoate, chlorantraniliprole, cyantraniliprole, fulvendiamide, pyridaben, sienopyraphene, chlorfenapyr, bacillus thuringiensis, pymetrozine, flonicamido An insecticidal, acaricidal, nematicidal, bactericidal or bactericidal composition as described in [1] or [2] above, which comprises an active compound II selected from, pyridalyl, bifenazate and fluxamethamide.

[4]
Pests produced by treating one or two active compounds I according to [1] above and one or more active compounds II according to [1] simultaneously or close in time Or disease control method.

[5]
The above by treating one or two active compounds I according to [2] above and one or two or more active compounds II according to [3] simultaneously or close in time [4] The pest or disease control method according to [4].

[6]
Treating seeds with one or two active compounds I according to [1] above and one or more active compounds II according to [1] simultaneously or close in time The pest or disease control method according to the above [4].

[7]
Treating seeds with one or two active compounds I according to [2] above and one or more active compounds II according to [3] simultaneously or close in time The pest or disease control method according to the above [6].

  The composition of the present invention and the method of the present invention exhibit an excellent synergistic control effect against various pests and a sufficient synergistic control effect against pests that have acquired resistance to existing pest control agents. Demonstrate.

  Therefore, the present invention can provide a useful novel pest control composition and an effective control method using them.

  Specific examples of each substituent shown in the present specification are shown below. Here, n- means normal, i- means iso, s- means secondary, and tert- means tertiary.

  Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.

In the present specification, the expression “C _a -C _b alkyl” represents a linear or branched hydrocarbon having a carbon number of _a to _b , for example, methyl, ethyl, n-propyl, i Specific examples include -propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl, etc., and each designated range of the number of carbon atoms. Selected.

In the present specification, the expression “halo (C _a -C _b ) alkyl” refers to a straight chain composed of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is arbitrarily substituted with a halogen atom, or A branched hydrocarbon is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 1 , 1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2-difluoro Propyl, 3,3,3-trifluoropropyl, 3-bromo-3,3-diph Olopropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2, 2,2-trifluoro-1- (methyl) ethyl, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) Specific examples include ethyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, etc. In the range of the number of carbon atoms.

In the present specification, the expression “halo (C _a -C _b ) alkylthio” represents haloalkyl-S— which has the above-mentioned meaning consisting of _a to _b carbon atoms, and includes, for example, difluoromethylthio, trifluoromethylthio, Chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethyl Thio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio and the like Specific examples are given, each selected in the range of the specified number of carbon atoms.

In the present specification, the expression “halo (C _a -C _b ) alkylsulfinyl” represents haloalkyl-S (O) — which has the above-mentioned meaning consisting of _a to _b carbon atoms, for example, difluoromethylsulfinyl. , Trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl, nonafluoro Specific examples include butylsulfinyl and the like, each selected within the range of the designated number of carbon atoms.

The expression “halo (C _a -C _b ) alkylsulfonyl” in the present specification represents the above-mentioned haloalkyl-SO ₂ — having a carbon number of _a to _b , for example, difluoromethylsulfonyl, tri Fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trifluoro Specific examples include ethylsulfonyl and the like, each selected within the range of the designated number of carbon atoms.

In the present specification, the expression “C _a -C _b alkylcarbonyl” represents alkyl-C (O) — having the above-mentioned meaning consisting of _a to _b carbon atoms, such as acetyl, propionyl, pivaloyl and the like. Are given as specific examples and are selected within the range of each designated number of carbon atoms.

  In the present specification, “the condensed heterocyclic compound represented by the formula (1)” is also described as “the compound (1)”, and “the compound represented by the formula (1-Q1)” is “the compound (1)”. -Q1) ". The other compounds are similarly described.

  The compound (1) contained in the active compound I which is the first active ingredient of the composition of the present invention will be described in detail below.

  Compound (1) includes an optically active substance resulting from the presence of one or more asymmetric carbon atoms or an asymmetric sulfur atom, but the present invention includes all optically active substances or racemates. .

  Among the compounds (1), those which can be converted into acid addition salts according to a conventional method are, for example, hydrohalic acid salts such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, nitric acid , Inorganic acid salts such as sulfuric acid, phosphoric acid, chloric acid, perchloric acid, sulfonic acid salts such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, formic acid, Acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid and other carboxylic acid salts or glutamic acid, It can be a salt of an amino acid such as aspartic acid.

  Among the compounds (1), those which can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium and potassium, alkaline earth metal salts such as calcium, barium and magnesium, and aluminum salts It can be.

  In the compound (1), N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocyclic ring is oxidized. Examples of the heterocyclic ring that can form an N-oxide include a condensed ring including a pyridine ring.

Compound (1) contained in active compound I which is the first active ingredient of the composition of the present invention can be produced, for example, by the following production methods 1 to 8.
[Production Method 1]
Among the compounds (1), Q is Q1 and n is an integer of 0 (1-Q1-b) and Q is Q1 and n is an integer of 1 or 2 (1-Q1- b) can be produced, for example, by the following production method.

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , Y 2, Y 3 and Y 4 represent the same meaning as described above, and m represents 1 or 2).
Step 1: Compound (2-Q1-b) is obtained by dehydrating and condensing compound (30) and compound (31-1-b) in the presence of a base (for example, pyridine, triethylamine, potassium carbonate, cesium carbonate, etc.). [For example, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, etc.] Can be produced by reacting with each other. In some cases, additives such as 1-hydroxybenzotriazole and 4- (dimethylamino) pyridine may be used. Some of the compounds (30) are known compounds, and some of them are available as commercial products.

  Step 2: Compound (1-Q1-b) is synthesized in the presence of an acid (eg, p-toluenesulfonic acid, polyphosphoric acid, acetic acid, propionic acid, etc.) or a dehydrating agent (eg, phosphorus oxychloride, acetic anhydride, etc.) It can be produced by subjecting 2-Q1-b) to a dehydration cyclization reaction.

Step 3: Compound (1-Q1-a) is an oxidizing agent [for example, peracids such as metachloroperbenzoic acid and peracetic acid, hydrogen peroxide, oxone (OXONE, trade name of EI DuPont); potassium peroxohydrogensulfate The compound (1-Q1-b) can be produced by oxidizing the compound using the In some cases, a catalyst (such as sodium tungstate) can be used.
[Production Method 2]
Among the compounds (1), the compound (1-Q1) in which Q is Q1 can be produced by the following production method.

^{(Wherein, R 1, R 3, A} 4, A 5, A 1a, Y2, Y3, Y4 and n are as defined above, J represents a leaving group such as a halogen atom.)
Step 1: Compound (2-Q1) is produced by reacting Compound (30) with Compound (31) in the presence of a base (for example, pyridine, triethylamine, sodium bicarbonate, potassium carbonate, cesium carbonate, etc.). be able to. Some of the compounds (30) are known compounds, and some of them are available as commercial products.

Step 2: The compound (1-Q1) can be produced by a method according to Step 2 of Production Method 1.
[Production Method 3]
Among the compounds (1), the compound (1-Q1-a) and the compound (1-Q1-b) can be produced by the following production method.

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , Y 2, Y 3, Y 4 and m represent the same meaning as described above, and X ¹ represents a halogen atom.)
Step 1: Compound (4) can be produced by reacting compound (9) with compound (34) under heating conditions according to the method described in International Publication No. 2007/148755. In some cases, a base (for example, pyridine, triethylamine, potassium carbonate, cesium carbonate, etc.) may be used. Some of the compounds (34) are known compounds, and some of them can be obtained as commercial products.

  Step 2: Of compound (1), compound (1-Q1-b) is a halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, Compound (4) and compound in the presence of 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, etc. (50) or by reacting with compound (59). Some of compound (50) and compound (59) are known compounds, and some of them are commercially available.

Process 3: A compound (1-Q1-a) can be manufactured by the method according to the manufacturing method 1, the process 3.
[Production Method 4]
Among the compounds (1), the compound (1-Q1-a) and the compound (1-Q1-b) can be produced by the following production method.

(In the formula, R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , Y 2, Y 3, Y 4, m and X ¹ represent the same meaning as described above.)
Step 1: Compound (1-Q1-b) can be produced by reacting compound (5) with compound (34) by the method according to production method 3, step 1. Some of the compounds (34) are known compounds, and some of them can be obtained as commercial products.

Process 2: A compound (1-Q1-a) can be manufactured by the method according to the manufacturing method 1, the process 3.
[Production Method 5]
Among the compounds (1-Q1), a compound (1-Q1-c) in which R ³ is trifluoromethanesulfinyl or trifluoromethanesulfonyl and a compound (1-Q1-d) in which R ³ is trifluoromethylthio are, for example, It can be produced by the following production method.

(In the formula, R ¹ , A ⁴ , A ⁵ , A ^1a , Y 2, Y 3, Y 4 and n represent the same meaning as described above, X ² represents a halogen atom, and q represents an integer of 1 or 2.)
Step 1: Compound (6-2) can be obtained according to Organic Letters 2007, 9, 3687, Tetrahedron 1998, 44, 1187, International Publication No. 2011/159839, etc. In accordance with the method described, the compound (6-1) produced according to the method described in Production Method 2 and a thiolating agent (for example, 2-ethylhexyl 3-mercaptopropionate, sodium hydrogen sulfide, sodium sulfide, etc.) Can be made to react.

  Step 2: Compound (1-Q1-d) is prepared according to the method described in International Publication No. 2013/043962, International Publication No. 2013/040863, International Publication No. 2012/082566, etc. ) And a trifluoromethylating agent [for example, Umemoto reagent (5- [trifluoromethyl] dibenzothiophenium trifluoromethanesulfonate), Togni reagent (1-trifluoromethyl-3,3-dimethyl-1,2-benzoiodoxy) Sole) and the like] can be reacted.

Process 3: A compound (1-Q1-c) can be manufactured by the method according to the manufacturing method 1, the process 3.
[Production Method 6]
Among the compounds (1), the compound (1-Q1) can be produced, for example, by reacting the compound (8-1) with the compound (35).

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , Y 2, Y 3 and Y 4 represent the same meaning as described above, and R ¹⁰ represents C ₁ -C ₆ alkylcarbonyl).
Compound (1-Q1) is prepared according to the method described in Organic Letters 2013, Vol. 15, page 6254, oxygen and a copper catalyst [for example, copper chloride (I), copper bromide (I), In the presence of copper iodide (I), copper oxide (I), copper chloride (II), copper trifluoromethanesulfonate (II), etc.], by reacting compound (8-1) with compound (35) Can be manufactured. In some cases, an acylating agent (for example, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) may be used. The compound (8-1) includes E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio. Some of the compounds (35) are known compounds, and some of them can be obtained as commercial products.
[Production Method 7]
Among the compounds (1), the compound (1-Q1-e) can be produced, for example, by the following production method.

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , Y 2, n and X ² represent the same meaning as described above, and R ¹⁰ and R ¹¹ are each independently C ₁ -C ₆ alkyl. Represents carbonyl.)
Step 1: Compound (7-1) is oxygen, copper catalyst [for example, copper chloride (I), copper bromide (I), copper iodide (I), copper oxide (I), copper chloride (II), trifluoro In the presence of copper (II) methanesulfonate and an acylating agent (for example, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.), compound (8-1) and compound (35- It can be produced by reacting with 2). The compound (8-1) includes E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio. Some of the compounds (35-2) are known compounds, and some of them are available as commercial products.

  Step 2: Compound (7-2) can be produced by hydrolyzing Compound (7-1) in the presence of an acid (for example, acetic acid, hydrochloric acid, sulfuric acid, etc.). In some cases, the acid may be used as a solvent.

  Step 3: A halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride) according to the method described in The Journal of Organic Chemistry, 1965, 30, 1101, etc. N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5 Compound (7-3) can be produced by reacting compound (7-2) with 5-dimethylhydantoin or the like.

Step 4: Compound (1-Q1-e) is an acid (for example, acetic acid, hydrochloric acid, sulfuric acid, etc.) according to the method described in Russian Chemical Bulletin 2004, 53, 471. In the presence, it can be produced by reacting nitrite (for example, sodium nitrite) with compound (7-3). In some cases, copper catalyst [eg, copper (I) chloride, copper bromide (I), copper iodide (I), copper oxide (I), copper chloride (II), copper trifluoromethanesulfonate (II), etc.] is used. May be.
[Production Method 8]
Among the compounds (1), a compound (1-Q2-a) in which Q is Q2 and n is an integer of 1 or 2, and a compound (1-Q2- in which Q is Q2 and n is 0) b) can be produced, for example, by the following production method.

(Wherein R ¹ , R ³ , Y 2, Y ³ , Y 4, n and X ¹ represent the same meaning as described above.)
Step 1: Compound (33-2) can be produced by reacting compound (33-1) with sodium azide according to a known method.

  Step 2: Compound (3) is prepared from a base (for example, pyridine, triethylamine, sodium bicarbonate, potassium carbonate, cesium carbonate, etc.) and a Lewis acid (for example, titanium tetrachloride) according to the method described in International Publication No. 2012/066061. Etc.) in the presence of the compound (33-2) and the compound (32). Compound (3) includes E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio.

  Step 3: Compound (1-Q2-b) can be produced by cyclizing compound (3) according to the method described in International Publication No. 2012/066061.

  Process 4: A compound (1-Q2-a) can be manufactured by the method according to the manufacturing method 1, the process 3.

Compound (31-1-b) used in Production Method 1 can be produced, for example, according to the following production method.
[Reaction Formula 1]

(Wherein R ¹ , Y 2, Y 3, Y 4 and X ¹ represent the same meaning as described above, R ^a represents C ₁ -C ₆ alkyl, and L ¹ represents a halogen atom.)
Step 1: Compound (42) is obtained by reacting Compound (34) and Compound (57) under heating conditions according to the methods described in International Publication No. 2013/087772, International Publication No. 2012/096929, etc. Can be manufactured. Some of the compound (34) and the compound (57) are known compounds, and some of them are commercially available.

  Step 2: Compound (42) and a halogenating agent (for example, chlorine, bromine, iodine) according to the method described in International Publication No. 2010/033978, International Publication No. 2011/075643, International Publication No. 2007/0875548, etc. N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5 Compound (43) can be produced by reacting with 5-dimethylhydantoin or the like.

  Step 3: According to the method described in Organic Letters 2007, Vol. 9, p. 3687, etc., a palladium catalyst [for example, palladium-carbon, palladium (II) chloride, palladium (II) acetate, bis (tri Phenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0) etc.] and a base (eg pyridine, Compound (31-2-b) can be produced by reacting compound (43) with compound (50) in the presence of triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and the like. In some cases, a ligand (for example, 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 1,10-phenanthroline, etc.) may be used.

  Step 4: Compound (31-1-b) can be produced by hydrolyzing compound (31-2-b) according to a known method.

The compound (31-2-b) can also be produced, for example, by the following method.
[Reaction Formula 2]

(In the formula, R ¹ , Y 2, Y 3, Y 4 and R ^a represent the same meaning as described above.)
Compound (31-2-b) can be produced by reacting compound (42) with compound (50) or compound (59) according to the method described in Step 2 of Production Method 3.

Of the compound (31) used in production method 2, compound (31-a) wherein n is 1 or 2 can be produced, for example, according to the following production method.
[Reaction Formula 3]

(In the formula, R ¹ , Y 2, Y 3, Y 4, m, R ^a and J have the same meaning as described above.)
Step 1: Compound (31-2-a) can be produced by oxidizing compound (31-2-b) according to the method described in Production Method 1.

  Step 2: Compound (31-1-a) can be produced by hydrolyzing compound (31-2-a) according to a known method.

  Step 3: In accordance with a known method, compound (31-1-a) and a halogenating agent (for example, hydrogen fluoride, potassium fluoride, oxalyl dichloride, thionyl chloride, phosphorus oxychloride, phosphorus oxybromide, bromide) Compound (31-a) can be produced by reacting with acetyl and the like.

Among compounds (31), compound (31-b) in which n is 0 can be produced, for example, according to the following production method.
[Reaction Formula 4]

(In the formula, R ¹ , Y 2, Y 3, Y 4 and J represent the same meaning as described above.)
Compound (31-b) can be produced by reacting compound (31-1-b) according to the method described in the step of Reaction Scheme 3.

Compound (9) used in production method 3 can be produced, for example, according to the production route represented by the following reaction formula.
[Reaction Formula 5]

(In the formula, R ³ , A ⁴ , A ⁵ , A ^1a , X ¹ and J represent the same meaning as described above.)
Step 1: Compound (30) and Compound (52) are condensed according to a known method, then Synthesis 1991, page 465, Bioorganic & Medicinal Chemistry Letters ) Deacetylation reaction according to the method described in 2011, Vol. 21, p. 4602, etc., followed by dehydration cyclization reaction according to the method described in Step 2 of Production Method 1 38) can be produced. Some of the compounds (52) are known compounds, and some of them can be obtained as commercial products.

  Step 2: Compound (39) is produced by oxidizing compound (38) according to the method described in Journal of Medicinal Chemistry 1982, Vol. 25, page 1342, etc. Can do.

  Step 3: Compound (9) is compound (39) and a halogenating agent (for example, chlorine, bromine, iodine, iodine monochloride, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro- 5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, trimethylphenylammonium tribromide, hydrobromic acid, acetic acid solution of hydrogen bromide Etc.) can be reacted. In some cases, additives such as hydrobromic acid and acetic acid solution of hydrogen bromide may be used.

  This step is produced by reacting compound (39) in the presence of a silylating agent (for example, trimethylsilyl trifluoromethanesulfonate) and a base (for example, pyridine, triethylamine, sodium bicarbonate, potassium carbonate, cesium carbonate, etc.). After making the silylated compound (39), the reaction with the halogenating agent can also be carried out. The silylated compound (39) may be directly reacted with a halogenating agent without isolation / purification.

  Although the compound (52) and the compound (38) have optically active substances resulting from the presence of one asymmetric carbon, they include all optically active substances and racemates.

Compound (5) used in production method 4 can be produced, for example, according to the production route represented by the following reaction formula.
[Reaction Scheme 6]

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a and X ¹ represent the same meaning as described above, X ³ represents a halogen atom, and W ¹ represents a hydrogen atom, a sodium atom or a potassium atom. .)
Step 1: Compound (10) can be produced by reacting compound (9) with compound (51) according to a known method. In some cases, a base (for example, pyridine, triethylamine, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, etc.) may be used. Some of the compounds (51) are known compounds, and some of them can be obtained as commercial products.

  Step 2: Compound (5) can be produced by reacting Compound (10) according to the method described in Step 3 of Reaction Scheme 5.

Of the compound (8-1) used in Step 1 of Production Method 6 and Production Method 7, compound (8-1-a) wherein n is an integer of 1 or 2 is represented by the following reaction formula, for example. It can be manufactured according to the manufacturing route.
[Reaction Scheme 7]

(Wherein R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , m, R ¹⁰ and X ¹ represent the same meaning as described above.)
Step 1: Compound (54) is prepared by reacting Compound (55) and Compound (56) in the presence of a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.). It can be produced by reacting.
Some of the compound (55) and the compound (56) are known compounds, and some of them are commercially available.

  Process 2: A compound (40-1) can be manufactured by performing the dehydration condensation reaction of a compound (30) and a compound (54) in presence of an acid (for example, an acetic acid, hydrochloric acid, a sulfuric acid, etc.). In some cases, a dehydrating agent (for example, anhydrous magnesium sulfate, anhydrous sodium sulfate, molecular sieve, silica gel, etc.) may be used. The usage-amount of a dehydrating agent can be used at 0.1-100 mass parts with respect to a compound (30), and 0.1-20 mass parts is preferable.

  Step 3: Compound (41-1) can be produced by reacting compound (40-1) according to the method described in Step 2 of Production Method 1.

  Step 4: Compound (8-2-a) can be produced by oxidizing compound (41-1) according to the method described in Step 3 of Production Method 1.

  Step 5: Compound (8-1-a) is compound (8-2-a) in the presence of a base (for example, pyridine, triethylamine, sodium hydrogen carbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.). ) And an acylating agent (for example, acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) be able to.

In the compound (55), the compound (54), the compound (40-1) and the compound (41-1), there are optically active substances resulting from the presence of one asymmetric carbon. Body and racemate. Moreover, a compound (8-2-a) and a compound (8-1-a) include the mixture which contains E body, Z body, or E body and Z body in arbitrary ratios.
[Reaction Formula 8]

(Wherein R ¹ , R ³ , R ¹⁰ , A ⁴ , A ⁵ , A ^1a and m have the same meaning as described above.)
Step 1: Compound (8-2-b) is prepared from a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide) according to the method described in International Publication No. 2001/83479, Japanese Patent No. 4237497, etc. In the presence of potassium carbonate, potassium hydroxide, cesium carbonate, etc.), hydroxylamine or a salt thereof (for example, hydrochloride, sulfate) and compound (10) produced by the method described in Reaction Scheme 6, Step 1 It can be produced by reacting.

  Step 2: Compound (8-2-a) can be produced by oxidizing compound (8-2-b) according to the method described in Step 3 of Production Method 1.

  Step 3: Compound (8-1-a) can be synthesized by acylating compound (8-2-a) according to the method described in Step 5 of Reaction Scheme 7.

  The compound (8-2-b), the compound (8-2-a) and the compound (8-1-a) include E-form, Z-form, or a mixture containing E-form and Z-form in an arbitrary ratio. .

Compound (41-1) used in Reaction Scheme 7 can be produced, for example, according to the production route represented by the following reaction formula.
[Reaction Scheme 9]

(In the formula, R ¹ , R ³ , A ⁴ , A ⁵ , A ^1a , R ¹¹ and J have the same meaning as described above.)
Step 1: A compound produced by the method according to Step 1 of Reaction Scheme 7 in the presence of a base (for example, pyridine, triethylamine, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, cesium carbonate, etc.) ( 54) and an acylating agent (for example, acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, acetic anhydride, propionic anhydride, isobutyric anhydride, pivalic anhydride, etc.) in a known manner. The compound (60) can be produced by reacting accordingly.

  Step 2: Compound (40-2) can be produced by subjecting compound (30) and compound (60) to a condensation reaction according to the method described in Step 2 of Reaction Scheme 7.

  Step 3: Compound (41-2) can be produced by subjecting compound (40-2) to a dehydration cyclization reaction according to the method described in Step 2 of Production Method 1.

  Step 4: Compound (41-1) can be produced by subjecting compound (41-2) to a deacylation reaction according to the method described in Step 2 of Production Method 7.

  The compound (54), the compound (60), the compound (40-2), the compound (41-2) and the compound (41-1) have an optically active substance resulting from the presence of one asymmetric carbon. However, all optically active forms and racemates are included.

Compound (32) used in production method 8 can be produced, for example, according to the production route represented by the following reaction formula.
[Reaction Scheme 10]

(In the formula, R ¹ , Y 2, Y 3 and Y 4 represent the same meaning as described above, and R ^b represents C _{1 to} C ₆ alkyl.)
Step 1: Compound (44) is compound (31-1-b), which can be produced according to Reaction Scheme 1, in the presence of alcohol (eg, methanol, ethanol, propanol, tertiary butanol, etc.) in the presence of diphenylphosphoryl azide ( It can be produced by reacting with (DPPA).

  Step 2: Compound (32) is prepared from Compound (44) in the presence of an acid (for example, hydrochloric acid, sulfuric acid, etc.) according to the methods described in International Publication Nos. 2012/174312 and 2003/018021. It can be produced by hydrolysis.

  In the reactions of production methods 1 to 8 and reaction formulas 1 to 10, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, washed with water, concentrated or put into ice water, and concentrated after extraction with an organic solvent. To obtain the desired compound. Moreover, when the necessity for purification arises, it can be separated and purified by a purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation or the like.

  Below, the synthesis example of the compound (1) contained in the active compound I which is the 1st active ingredient of this invention composition is demonstrated concretely.

  For medium pressure preparative liquid chromatography, medium pressure preparative apparatus (YFLC-Wprep, manufactured by Yamazen Co., Ltd .; flow rate: 18 ml / min; silica gel 40 μm column) was used.

A proton nuclear magnetic resonance spectrum (hereinafter referred to as ¹ H-NMR) was measured at 300 MHz (JNM-ECX300 or JNM-ECP300, manufactured by JEOL). As the measurement solvent, deuterated chloroform, deuterated dimethyl sulfoxide or deuterated water was used. When deuterated chloroform was used as a solvent, tetramethylsilane was used as a reference substance.

The symbol in the chemical shift value of ¹ H-NMR represents the following meaning.
s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet Synthesis Example 1: 2- [3- (ethylsulfonyl) -6- (trifluoromethyl) ) Synthesis of imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine (Compound No. 1-004)

Step 1: 2- [3- (Ethylthio) -6- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [ Synthesis of 4,5-b] pyridine N ² -methyl-5- (trifluoromethyl) pyridine-2,3-diamine 191 mg, 3- (ethylthio) -6- (trifluoromethyl) imidazo [1,2-a ] To a mixed solution of 291 mg of pyridine-2-carboxylic acid, 40 mg of 4- (dimethylamino) pyridine and 10 ml of pyridine, 384 mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride was added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The obtained organic layer was washed with 1 mol / L hydrochloric acid, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 3- (ethylthio) -N -300 mg of a crude product of [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide was obtained. It was. A mixed solution of 300 mg of the crude product and 10 ml of acetic acid was stirred for 5 hours under heating to reflux. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (10 ml × 2). The obtained organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 220 mg of the desired product as a light gray solid.

¹ H-NMR (CDCl ₃ ): δ9.05-8.95 (m, 1H), 8.72 (s, 1H), 8.40 (s, 1H), 7.82 (d, J = 9.7Hz, 1H), 7.52 (dd, J = 9.7, 1.9Hz, 1H), 4.31 (s, 3H), 3.14 (q, J = 7.4Hz, 2H), 1.22 (t, J = 7.4Hz, 3H).
Step 2: 2- [3- (Ethylsulfonyl) -6- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo Synthesis of [4,5-b] pyridine (Compound No. 1-004) To a mixed solution of 150 mg of the light gray solid obtained in Step 1 and 10 ml of chloroform, 65% by weight of metachloroperbenzoic acid (Tokyo) was added under ice cooling. (Made by Kasei Kogyo Co., Ltd .; containing about 30% by weight of water. The same applies hereinafter.) 134 mg was added. After the addition was complete, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 5 ml of a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, followed by extraction with chloroform (10 ml × 2). The obtained organic layer was washed with 10 ml of a 1 mol / L sodium hydroxide aqueous solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography [gradient of n-hexane: ethyl acetate = 100: 0 to 50:50 (volume ratio; the same applies hereinafter)] to obtain 69 mg of the desired product. Obtained as a white solid.

¹ H-NMR (CDCl ₃ ): δ9.68-9.63 (m, 1H), 8.76 (s, 1H), 8.35 (s, 1H), 7.95 (d, J = 9.5Hz, 1H), 7.71 (d, J = 9.5Hz, 1H), 4.17 (s, 3H), 4.12 (q, J = 7.2Hz, 2H), 1.26 (t, J = 7.2Hz, 3H).
Synthesis Example 2: 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H- Synthesis of imidazo [4,5-c] pyridine (Compound No. 2-001) Step 1: 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2- Synthesis of Nyl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-c] pyridine 303 mg of N ³ -methyl-6- (trifluoromethyl) pyridine-3,4-diamine and pyridine To 15 ml of the mixed solution, at room temperature, 552 mg of 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid and 1-ethyl-3- (3-dimethyla 732 mg of minopropyl) carbodiimide hydrochloride was added. After the addition was complete, the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give 3- (ethylthio) -N- [5- (methylamino) -2- (trifluoromethyl) pyridine- 986 mg of a crude product of 4-yl] -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide was obtained. A mixed solution of 986 mg of this crude product and 15 ml of acetic acid was stirred for 22 hours under heating to reflux. After completion of stirring, the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and the mixture was extracted with chloroform (10 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (n-hexane: ethyl acetate = 100: 0 to 70:30 gradient) to obtain 358 mg of the desired product as a yellow solid.

Melting point: 217-219 ° C
¹ H-NMR (CDCl ₃ ): δ8.97 (s, 1H), 8.78 (d, J = 7.2Hz, 1H), 8.20 (s, 1H), 8.05 (s, 1H), 7.22 (d, J = 7.2Hz, 1H), 4.37 (s, 3H), 3.15 (q, J = 7.5Hz, 2H), 1.22 (t, J = 7.5Hz, 3H).
Step 2: 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo Synthesis of [4,5-c] pyridine (Compound No. 2-001) To a mixed solution of 258 mg of the yellow solid obtained in Step 1 and 8 ml of chloroform, 323 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. did. After the addition was complete, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml). The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain the desired product 200m as a yellow solid.

Melting point: 245-247 ° C
¹ H-NMR (CDCl ₃ ): δ 9.39 (d, J = 7.2Hz, 1H), 9.00 (s, 1H), 8.14 (s, 2H), 7.33 (d, J = 7.2Hz, 1H), 4.20 (s, 3H), 4.07 (q, J = 7.5Hz, 2H), 1.46 (t, J = 7.5Hz, 3H).
Synthesis Example 3: 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H- Synthesis of imidazo [4,5-c] pyridine (Compound No. 2-001) N ³ -methyl-6- (trifluoromethyl) pyridine-3,4-diamine 200 mg and 1,3-dimethyl-2-imidazolid To a mixed solution of 5 ml of non, 340 mg of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid chloride was added at room temperature. After the addition was complete, the mixture was stirred at 140 ° C. for 5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with chloroform (10 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0-50: 50) to obtain 226 mg of the desired product as a white solid.

¹ H-NMR (CDCl ₃ ): δ 9.39 (d, J = 7.2Hz, 1H), 9.00 (s, 1H), 8.14 (s, 2H), 7.33 (d, J = 7.2Hz, 1H), 4.20 (s, 3H), 4.07 (q, J = 7.5Hz, 2H), 1.46 (t, J = 7.5Hz, 3H).
Synthesis Example 4: 3- (Ethylsulfonyl) -6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1, Synthesis of 2-a] pyridine-8-carbonitrile (Compound No. 1-007) Step 1: 6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5- b] Synthesis of Pyridin-2-yl] imidazo [1,2-a] pyridine-8-carbonitrile 2 ml of a mixed solution of 2-amino-3-cyano-5-iodopyridine and 5 ml of acetonitrile at room temperature -Bromo-1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one 500 mg was added. After the addition was complete, the mixture was stirred for 5 hours under heating to reflux. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was filtered to obtain 337 mg of the desired product as a white solid.

Melting point: 284-285 ° C
Step 2: 3- (Ethylthio) -6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2- a] Synthesis of pyridine-8-carbonitrile To a mixed solution of 337 mg of the white solid obtained in Step 1 and 5 ml of 1,2-dichloroethane, 264 mg of diethyl disulfide and 192 mg of N-chlorosuccinimide were sequentially added at room temperature. After the addition was complete, the mixture was stirred for 1.5 hours under heating to reflux. Thereafter, 440 mg of diethyl disulfide and 385 mg of N-chlorosuccinimide were sequentially added to the reaction mixture at room temperature, and the mixture was stirred for 1 hour with heating under reflux. Thereafter, 880 mg of diethyl disulfide and 770 mg of N-chlorosuccinimide were sequentially added to the reaction mixture at room temperature, and the mixture was stirred for 2 hours under heating to reflux. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with chloroform (10 ml × 2). The obtained organic layer was washed with 10 ml of a 1 mol / L sodium hydroxide aqueous solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 197 mg of the desired product as a white solid.
¹ H-NMR (CDCl ₃ ): δ9.08 (d, J = 1.7Hz, 1H), 8.76-8.73 (m, 1H), 8.42-8.39 (m, 1H), 7.96 (d, J = 1.7Hz, 1H), 4.40 (s, 3H), 3.20 (q, J = 7.4Hz, 2H), 1.25 (t, J = 7.4Hz, 3H).
Step 3: 3- (Ethylsulfonyl) -6-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2 -A] Synthesis of pyridine-8-carbonitrile (Compound No. 1-007) To a mixed solution of 182 mg of the white solid obtained in Step 2 and 5 ml of chloroform, 201 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. Added. After the addition was complete, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, 5 ml of a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, followed by extraction with chloroform (10 ml × 2). The obtained organic layer was washed with 10 ml of a 1 mol / L sodium hydroxide aqueous solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (n-hexane: ethyl acetate = 100: 0 to 50:50 gradient) to obtain 155 m of the desired product as a white solid.

¹ H-NMR (CDCl ₃ ): δ9.74 (d, J = 1.5Hz, 1H), 8.78 (d, J = 1.8Hz, 1H), 8.36 (d, J = 1.8Hz, 1H), 8.14 (d , J = 1.5Hz, 1H), 4.25 (s, 3H), 4.19 (q, J = 7.5Hz, 2H), 1.48 (t, J = 7.5Hz, 3H).
Synthesis Example 5: 2- [3- (Ethylsulfonyl) -6-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 5-b] Synthesis of Pyridine (Compound No. 1-003) Step 1: 2- [3- (Ethylthio) -6-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one and a mixed solution of 3.0 g of acetonitrile and 25 ml of acetonitrile were added 3.17 g of 5-iodopyridin-2-amine at room temperature. After the addition was complete, the mixture was stirred for 7 hours under heating to reflux. After completion of the reaction, 40 ml of water was added to the reaction mixture. The precipitated solid was filtered, and the obtained solid was washed with diisopropyl ether to obtain 1.36 g of the desired product as a light brown solid.
¹ H-NMR (CDCl ₃ ): δ8.91-8.88 (m, 1H), 8.73-8.70 (m, 1H), 8.41-8.39 (m, 1H), 7.56 (dd, J = 9.3, 1.8Hz, 1H ), 7.50 (d, J = 9.3Hz, 1H), 4.29 (s, 3H), 3.08 (q, J = 7.2Hz, 2H), 1.21 (t, J = 7.2Hz, 3H).
Step 2: 2- [3- (Ethylsulfonyl) -6-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of Pyridine (Compound No. 1-003) To a mixed solution of 1.36 g of the light brown solid obtained in Step 1 and 10 ml of chloroform, 1.29 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. Added. After the addition was complete, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with chloroform (20 ml × 2). The obtained organic layer was washed with 20 ml of a 1 mol / L aqueous sodium hydroxide solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated solid was filtered, and the obtained solid was washed with diisopropyl ether to obtain 972 mg of the desired product as a pale yellow solid.

¹ H-NMR (CDCl ₃ ): δ 9.49 (s, 1H), 8.75 (s, 1H), 8.35 (s, 1H), 7.75 (dd, J = 9.3, 1.2Hz, 1H), 7.61 (d, J = 9.3Hz, 1H), 4.13 (s, 3H), 4.01 (q, J = 7.2Hz, 2H), 1.46 (t, J = 7.2Hz, 3H).
Synthesis Example 6: 2- [3- (Ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 5-b] Synthesis of Pyridine (Compound No. 1-006) Step 1: 2- [3- (Ethylthio) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one 1.7 g of 4-iodo-2-aminopyridine at room temperature was added to a mixed solution of 3.0 g of acetonitrile and 26 ml of acetonitrile. After the addition was complete, the mixture was stirred for 7 hours under heating to reflux. After completion of the reaction, 100 ml of water was added to the reaction mixture at room temperature. The precipitated solid was filtered to obtain 1.56 g of the target product as a light brown solid.
¹ H-NMR (CDCl ₃ ): δ8.75-8.65 (m, 1H), 8.40-8.35 (m, 2H), 8.20-8.10 (m, 1H), 7.30-7.20 (m, 1H), 4.28 (s , 3H), 3.08 (q, J = 7.8Hz, 2H), 1.18 (t, J = 7.8Hz, 3H).
Step 2: 2- [3- (Ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of Pyridine (Compound No. 1-006) To a mixed solution of 1.56 g of the light brown solid obtained in Step 1 and 10 ml of chloroform, 1.73 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. Added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, 10 ml of a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, followed by extraction with chloroform (10 ml × 2). The obtained organic layer was washed with 10 ml of 1 mol / L sodium hydroxide aqueous solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The precipitated solid was filtered, and the obtained solid was washed with 10 ml of diisopropyl ether to obtain 1.24 g of the desired product as a pale yellow solid.
¹ H-NMR (CDCl ₃ ): δ8.99 (dd, J = 7.5, 0.6Hz, 1H), 8.75 (d, J = 1.2Hz, 1H), 8.33 (d, J = 1.2Hz, 1H), 8.30 -8.26 (m, 1H), 7.38 (dd, J = 7.2, 1.2Hz, 1H), 4.13 (s, 3H), 4.02 (q, J = 7.5Hz, 2H), 1.43 (t, J = 7.5Hz, 3H).
Synthesis Example 7: 2- [7-chloro-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 5-b] Synthesis of Pyridine (Compound No. 1-005) Step 1: 2- [7-Chloro-3- (ethylthio) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6 Synthesis of-(trifluoromethyl) -3H-imidazo [4,5-b] pyridine 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4 , 5-b] pyridin-2-yl] ethane-1-one 828 mg and acetonitrile 7 ml mixed solution was added 4-chloropyridin-2-amine 334 mg at room temperature. After the addition was complete, the mixture was stirred for 5 hours under heating to reflux. After completion of the reaction, 30 ml of water was added to the reaction mixture at room temperature. The precipitated solid was filtered, and the obtained solid was washed with 10 ml of diisopropyl ether to obtain 447 mg of the desired product as a yellow solid.
¹ H-NMR (CDCl ₃ ): δ8.70 (d, J = 1.6Hz, 1H), 8.57 (d, J = 7.4Hz, 1H), 8.37 (s, 1H), 7.71 (d, J = 1.6Hz , 1H), 7.02 (dd, J = 7.4, 1.6Hz, 1H), 4.28 (s, 3H), 3.07 (q, J = 7.5Hz, 2H), 1.19 (t, J = 7.5Hz, 3H).
Step 2: 2- [7-Chloro-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of pyridine (Compound No. 1-005) To a mixed solution of 4.18 g of yellow solid synthesized by the method of Step 1 and 20 ml of chloroform, 6.20 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, 30 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with chloroform (30 ml × 2). The obtained organic layer was washed with 50 ml of 1 mol / L sodium hydroxide aqueous solution, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 30:70) to obtain 2.89 g of the desired product as a white solid.
¹ H-NMR (CDCl ₃ ): δ9.18 (d, J = 7.4Hz, 1H), 8.74 (s, 1H), 8.33 (d, J = 1.2Hz, 1H), 7.85-7.80 (m, 1H) , 7.15-7.10 (m, 1H), 4.14 (s, 3H), 4.03 (q, J = 7.4Hz, 2H), 1.43 (t, J = 7.4Hz, 3H).
Synthesis Example 8 2- [3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-((trifluoromethyl) sulfinyl) Synthesis of -3H-imidazo [4,5-b] pyridine (Compound No. 1-009) Step 1: 3- (Ethylthio) -N- [5-iodo-2- (methylamino) pyridin-3-yl] Synthesis of -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide To a mixed solution of 5-iodo-N ² -methylpyridine-2,3-diamine and 15 ml of pyridine at room temperature 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid 1.54 g and 1-ethyl-3- (3-dimethylaminopropyl) carbonate. 2.45 g of rubodiimide hydrochloride was added sequentially. After the addition was complete, the mixture was stirred at room temperature overnight. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was filtered to obtain a target crude product as a gray solid (2.49 g).

¹ H-NMR (CDCl ₃ ): δ8.97 (brs, 1H), 8.71 (d, J = 7.2Hz, 1H), 8.27 (d, J = 2.0Hz, 1H), 8.07 (d, J = 2.0Hz , 1H), 7.96 (s, 1H), 7.19 (dd, J = 7.2, 2.0Hz, 1H), 4.78 (brs, 1H), 3.08 (q, J = 7.4Hz, 2H), 3.03 (d, J = 4.8Hz, 3H), 1.22 (t, J = 7.4Hz, 3H).
Step 2: 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -6-iodo-3-methyl-3H-imidazo [4,5- b] Synthesis of pyridine A mixed solution of 2.49 g of the gray solid obtained in Step 1 and 15 ml of acetic acid was stirred for 3.5 hours under heating to reflux. After completion of the reaction, water was added to the reaction mixture. The precipitated solid was filtered, and the obtained solid was washed with n-hexane to obtain 2.02 g of the desired product as a brown solid.

Melting point: 230-233 ° C
¹ H-NMR (CDCl ₃ ): δ8.76 (d, J = 7.2Hz, 1H), 8.62 (d, J = 1.7Hz, 1H), 8.47 (d, J = 1.7Hz, 1H), 8.03 (s , 1H), 7.19 (dd, J = 7.2, 1.7Hz, 1H), 4.25 (s, 3H), 3.11 (q, J = 7.5Hz, 2H), 1.20 (t, J = 7.5Hz, 3H).
Step 3: 2-ethylhexyl 3-[(2- [3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-3H-imidazo Synthesis of [4,5-b] pyridin-6-yl) thio] propanoate To a mixed solution of 503 mg of the brown solid obtained in Step 2 and 10 ml of 1,4-dioxane at room temperature, 387 mg of diisopropylethylamine, 4,5 -58 mg of bis (diphenylphosphino) -9,9-dimethylxanthene, 92 mg of tris (dibenzylideneacetone) dipalladium (0), and 262 mg of 2-ethylhexyl 3-mercaptopropionate were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, and then stirred for 4 hours under heating and reflux. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with diethyl ether (10 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (n-hexane: ethyl acetate = 100: 0 to 80:20 gradient) to obtain 599 mg of the desired product as a yellow solid.

Melting point: 94-96 ° C
¹ H-NMR (CDCl ₃ ): δ8.76 (d, J = 7.2Hz, 1H), 8.53 (d, J = 2.0Hz, 1H), 8.27 (d, J = 2.0Hz, 1H), 8.03 (s , 1H), 7.18 (dd, J = 7.2, 1.9Hz, 1H), 4.27 (s, 3H), 4.01 (dd, J = 5.8, 1.7Hz, 2H), 3.20-3.05 (m, 4H), 2.62 ( t, J = 7.3Hz, 2H), 1.45-1.20 (m, 12H), 0.89 (t, J = 7.5Hz, 6H).
Step 4: 2- [3- (Ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) thio] -3H -Synthesis of imidazo [4,5-b] pyridine Under a nitrogen atmosphere, 159 mg of potassium tert-butoxide was added to a mixed solution of 560 mg of the yellow solid obtained in Step 3 and 5 ml of tetrahydrofuran under ice cooling. After the addition was complete, the mixture was stirred for 30 minutes under ice cooling. Thereafter, 756 mg of 5- (trifluoromethyl) dibenzothiophenium trifluoromethanesulfonate was added to the reaction mixture at the same temperature, and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, water was added to the reaction mixture and extracted with chloroform (10 ml × 2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0-80: 20) to obtain 69 mg of the desired product as a pale yellow solid.

Melting point: 209-210 ° C
¹ H-NMR (CDCl ₃ ): δ8.77 (d, J = 7.2Hz, 1H), 8.66 (d, J = 2.0Hz, 1H), 8.46 (d, J = 2.0Hz, 1H), 8.05-8.02 (m, 1H), 7.20 (dd, J = 7.2, 1.9Hz, 1H), 4.31 (s, 3H), 3.14 (q, J = 7.4Hz, 2H), 1.21 (t, J = 7.4Hz, 3H) .
Step 5: 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) thio]- Synthesis of 3H-imidazo [4,5-b] pyridine To a mixed solution of 31 mg of the pale yellow solid obtained in Step 4 and 3 ml of chloroform, 38 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml × 2). The obtained organic layer was washed with a 1 mol / L sodium hydroxide aqueous solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 34 mg of the desired product as a white solid.

Melting point: 220-223 ° C
¹ H-NMR (CDCl ₃ ): δ9.41 (d, J = 7.4Hz, 1H), 8.70 (d, J = 2.0Hz, 1H), 8.41 (dJ = 2.0Hz, 1H), 8.14 (s, 1H ), 7.31 (dd, J = 7.4, 1.6Hz, 1H), 4.16 (s, 3H), 4.11 (q, J = 7.4Hz, 2H), 1.45 (t, J = 7.4Hz, 3H).
Step 6: 2- [3- (Ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridin-2-yl] -3-methyl-6-[(trifluoromethyl) sulfinyl]- Synthesis of 3H-imidazo [4,5-b] pyridine (Compound No. 1-009) To a mixed solution of 75 mg of a white solid synthesized by the method of Step 5 and 5 ml of chloroform, 65 wt% metachloroperoxide was added under ice cooling. 43 mg of benzoic acid was added. After the addition was complete, the mixture was stirred at room temperature for 24 hours. Thereafter, 8 mg of 65 wt% metachloroperbenzoic acid was added to the reaction mixture and the reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, 5 ml of a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, followed by extraction with chloroform (10 ml × 2). The obtained organic layer was washed with 10 ml of a 1 mol / L aqueous sodium hydroxide solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 35 mg of the desired product as a white solid.

¹ H-NMR (CDCl ₃ ): δ9.42 (d, J = 7.5Hz, 1H), 8.79 (d, J = 2.0Hz, 1H), 8.60 (d, J = 2.0Hz, 1H), 8.19-8.15 (m, 1H), 7.34 (dd, J = 7.5, 1.7Hz, 1H), 4.21 (s, 3H), 4.12 (q, J = 7.5Hz, 2H), 1.48 (t, J = 7.5Hz, 3H) .
Synthesis Example 9 2- [3- (ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 5-b] Synthesis of pyridine (Compound No. 1-006) (Z) -2- (Ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b ] Pyridin-2-yl] ethane-1-one O-acetyl oxime 589 mg, 4-iodopyridine 922 mg, copper (I) iodide 76 mg and N-methylpyrrolidone 15 ml mixed solution was stirred at 60 ° C. for 18 hours. . The reaction mixture was then stirred at 80 ° C. for 24 hours. Further thereafter, the reaction mixture was stirred at 100 ° C. for 4 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The obtained filtrate and washing solution were combined and the solvent was distilled off under reduced pressure. 30 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (30 ml × 3). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 10 mg of the desired product as a white solid.
¹ H-NMR (CDCl ₃ ): δ8.99 (dd, J = 7.5, 0.6Hz, 1H), 8.75 (d, J = 1.2Hz, 1H), 8.33 (d, J = 1.2Hz, 1H), 8.30 -8.26 (m, 1H), 7.38 (dd, J = 7.2, 1.2Hz, 1H), 4.13 (s, 3H), 4.02 (q, J = 7.5Hz, 2H), 1.43 (t, J = 7.5Hz, 3H).
Synthesis Example 10: 2- [3- (ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4 5-b] Synthesis of pyridine (Compound No. 1-006) Step 1: N- [3- (ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 Synthesis of (b) pyridin-2-yl) imidazo [1,2-a] pyridin-8-yl] acetamide (Z) -2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) ) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one O-acetyl oxime 90 mg, 3-aminopyridine 70 mg, copper (II) trifluoromethanesulfonate 30 mg and N-methylpyro In a mixed solution of Don 1 ml, at room temperature, it was added acetic anhydride 70 mg. After the addition was complete, the mixture was stirred at room temperature for 20 hours. The reaction mixture was then stirred at 60 ° C. for 4 hours. Further thereafter, the reaction mixture was stirred at 80 ° C. for 11 hours. After completion of the reaction, 10 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with chloroform (20 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 30:70) to obtain 43 mg of the desired product as a yellow solid.

¹ H-NMR (CDCl ₃ ): δ8.82 (dd, J = 6.9, 1.2Hz, 1H), 8.75 (d, J = 1.8Hz, 1H), 8.52 (d, J = 6.9Hz, 1H), 8.47 (brs, 1H), 8.34 (d, J = 1.8Hz, 1H), 7.20-7.10 (m, 1H), 4.07 (s, 3H), 3.81 (q, J = 7.2Hz, 2H), 2.33 (s, 3H), 1.40 (t, J = 7.2Hz, 3H).
Step 2: 3- (Ethylsulfonyl) -2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2-a] pyridine Synthesis of -8-amine To a mixed solution of 1.36 g of the yellow solid synthesized by the method of Step 1 and 10 ml of dichloromethane, 3.72 g of trifluoroacetic acid was added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 1 hour. Thereafter, 1.49 g of trifluoroacetic acid was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of toluene was added to the reaction mixture, and the solvent was distilled off under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the obtained residue, and the mixture was extracted with chloroform (10 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.27 g of the desired product as a yellow resinous substance.

¹ H-NMR (CDCl ₃ ): δ8.74 (s, 1H), 8.58 (d, J = 7.0Hz, 1H), 8.34 (s, 1H), 6.96 (t, J = 7.2Hz, 1H), 6.67 (d, J = 7.4Hz, 1H), 4.71 (s, 2H), 4.10 (s, 3H), 3.85 (q, J = 7.4Hz, 2H), 1.41 (t, J = 7.6Hz, 3H).
Step 3: 3- (Ethylsulfonyl) -7-iodo-2- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] imidazo [1,2 -A] Synthesis of Pyridin-8-amine To a mixed solution of 1.27 g of the yellow resinous substance obtained in Step 2 and 50 ml of N, N-dimethylformamide at room temperature, 1,3-diiodo-5,5- 494 mg of dimethylhydantoin was added. After the addition was complete, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 50 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 ml × 3). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 90: 10 to 0: 100) to obtain 1.39 g of the desired product as a yellow solid.

¹ H-NMR (CDCl ₃ ): δ 8.74 (d, J = 2.0Hz, 1H), 8.38 (d, J = 7.4Hz, 1H), 8.34 (d, J = 2.0Hz, 1H), 7.26 (d, J = 7.4 Hz, 1H), 5.12 (s, 2H), 4.09 (s, 3H), 3.89 (q, J = 7.5Hz, 2H), 1.40 (t, J = 7.4 Hz, 3H).
Step 4: 2- [3- (Ethylsulfonyl) -7-iodoimidazo [1,2-a] pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5 -B] Synthesis of pyridine (Compound No. 1-006) In a mixed solution of 80 mg of the yellow solid obtained in Step 3, 3 ml of ethanol and 0.5 ml of acetic acid, 46 mg of copper (I) oxide and sodium nitrite at room temperature. 100 mg water 0.5 ml solution was added sequentially. After the addition was complete, the mixture was stirred at room temperature for 17 hours. After completion of the reaction, 87 mg of urea in 3 ml of water was added to the reaction mixture, and the solvent was distilled off under reduced pressure. Ethyl acetate (50 ml) was added to the obtained residue and washed with 50 ml of 28 wt% aqueous ammonia. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 80: 20 to 60:40) to obtain 41 mg of the desired product as a white solid.
¹ H-NMR (CDCl ₃ ): δ8.99 (dd, J = 7.5, 0.6Hz, 1H), 8.75 (d, J = 1.2Hz, 1H), 8.33 (d, J = 1.2Hz, 1H), 8.30 -8.26 (m, 1H), 7.38 (dd, J = 7.2, 1.2Hz, 1H), 4.13 (s, 3H), 4.02 (q, J = 7.5Hz, 2H), 1.43 (t, J = 7.5Hz, 3H).
Synthesis Example 11 2- [6-Bromo-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -6- (trifluoromethyl) -2H-pyrazolo [4,3-c] Synthesis of pyridine (Compound No. 3-001) Step 1: Synthesis of 4-azido-6- (trifluoromethyl) nicotinaldehyde 1.50 g of 4-chloro-6- (trifluoromethyl) nicotinaldehyde and N, N- To a mixed solution of 10 ml of dimethylformamide, 511 mg of sodium azide was added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with diethyl ether (20 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 80:20) to obtain 2.13 g of the desired product as a white solid.

Melting point: 54-56 ° C
¹ H-NMR (CDCl ₃ ): δ 10.39 (s, 1H), 9.06 (s, 1H), 7.54 (s, 1H).
Step 2: of 2- [6-Bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-yl] -6- (trifluoromethyl) -2H-pyrazolo [4,3-c] pyridine Synthesis A mixed solution of 400 mg of white solid obtained in Step 1, 6-bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-amine 503 mg and dichloromethane 10 ml was mixed with 562 mg of triethylamine under ice cooling. Then, 1.11 ml of a dichloromethane solution (manufactured by Tokyo Chemical Industry Co., Ltd.) of about 1 mol / L titanium chloride (IV) was sequentially added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was filtered through celite, and the celite was washed with 30 ml of xylene. The obtained washing liquid was stirred for 3 hours under heating to reflux. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with chloroform (30 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0-50: 50) to obtain 441 mg of the desired product as a brown solid.
¹ H-NMR (CDCl ₃ ): δ9.38-9.36 (m, 1H), 9.27 (d, J = 1.0Hz, 1H), 8.77 (d, J = 1.0Hz, 1H), 8.14 (s, 1H) , 7.61 (d, J = 9.5Hz, 1H), 7.52 (dd, J = 9.5, 1.9Hz, 1H), 2.98 (q, J = 7.4Hz, 2H), 1.22 (t, J = 7.4Hz, 3H) .
Step 3: 2- [6-Bromo-3- (ethylsulfonyl) imidazo [1,2-a] pyridin-2-yl] -6- (trifluoromethyl) -2H-pyrazolo [4,3-c] pyridine Synthesis of (Compound No. 3-001) To a mixed solution of 350 mg of the brown solid obtained in Step 1 and 5 ml of chloroform, 483 mg of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the mixture was stirred at room temperature overnight. After completion of the reaction, a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml × 2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0-50: 50) to obtain 268 mg of the desired product as a yellow solid.
¹ H-NMR (CDCl ₃ ): δ9.42-9.41 (m, 1H), 9.39-9.37 (m, 1H), 9.03 (d, J = 1.0Hz, 1H), 8.08 (s, 1H), 7.71- 7.69 (m, 2H), 3.96 (q, J = 7.5Hz, 2H), 1.48 (t, J = 7.5Hz, 3H).
Next, the synthesis example of the synthetic intermediate of the compound (1) which is the first active ingredient of the composition of the present invention will be specifically described.

Intermediate Synthesis Example 1: Synthesis of 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid Step 1: Ethyl 7- (trifluoromethyl) imidazo [1, 2-a] Synthesis of pyridine-2-carboxylate Ethyl 3-bromo-2-oxopropanoate in a mixed solution of 5.0 g of 4- (trifluoromethyl) pyridin-2-amine and 50 ml of chlorobenzene at room temperature 6.67 g was added. After completion of the addition, the mixture was stirred for 6.5 hours under heating to reflux. After completion of the reaction, 20 ml of a 1 mol / L aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 3 mol / L hydrochloric acid was added to the obtained residue, and the mixture was washed with 10 ml of ethyl acetate. The aqueous layer was adjusted to pH 2-3 with 10 mol / L sodium hydroxide aqueous solution, and extracted with ethyl acetate (10 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.94 g of the desired product as a yellow solid.

Melting point: 170-175 ° C
_{^{1 H-NMR (CDCl 3)}} : δ8.29 (s, 1H), 8.27 (d, J = 7.2Hz, 1H), 8.01 (s, 1H), 7.07 (dd, J = 7.2, 1.7Hz, 1H) , 4.49 (q, J = 7.2Hz, 2H), 1.46 (t, J = 7.2Hz, 3H).
Step 2: Synthesis of ethyl 3-iodo-7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate 3.73 g of yellow solid obtained in Step 1 and 20 ml of N, N-dimethylformamide 6.5 g of N-iodosuccinimide was added to the mixed solution at room temperature. After the addition was complete, the mixture was stirred at 80 ° C. for 5 hours. After completion of the reaction, water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was dissolved in 20 ml of chloroform, and washed with a saturated aqueous sodium thiosulfate solution and then with saturated sodium hydrogen carbonate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 5.08 g of the desired product as a light orange solid.

Melting point: 183-185 ° C
¹ H-NMR (CDCl ₃ ): δ 8.40 (d, J = 7.2Hz, 1H), 7.99 (s, 1H), 7.17 (dd, J = 7.2, 1.7Hz, 1H), 4.53 (q, J = 7.2Hz, 2H), 1.50 (t, J = 7.2Hz, 3H).
Step 3: Synthesis of ethyl 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate 5.73 g and 1,4- of the pale orange solid obtained in Step 2 In a solution of 40 ml of dioxane, 5.79 g of diisopropylethylamine, 862 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 682 mg of tris (dibenzylideneacetone) dipalladium (0) and ethanethiol at room temperature 1.85 g was added sequentially. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, and then stirred for 2 hours under heating and reflux. After completion of the reaction, the reaction mixture was filtered through celite, and the celite was washed with 30 ml of chloroform. The obtained filtrate and washing solution were combined and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 5.58 g of the desired product as a brown solid.

Melting point: 50-52 ° C
¹ H-NMR (CDCl ₃ ): δ 8.67 (d, J = 7.4Hz, 1H), 8.02-8.00 (m, 1H), 7.15 (dd, J = 7.4, 1.8Hz, 1H), 4.52 (q, J = 7.0Hz, 2H), 2.98 (q, J = 7.5Hz, 2H), 1.48 (t, J = 7.0Hz, 3H), 1.20 (t, J = 7.5Hz, 3H).
Step 4: Synthesis of 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid 5.58 g of the brown solid obtained in Step 3, 60 ml of ethanol and 30 ml of tetrahydrofuran To the mixed solution, 10 ml of a 3 mol / L aqueous sodium hydroxide solution was added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 1 mol / L hydrochloric acid was added to the obtained residue to adjust the pH of the aqueous layer to 2, followed by extraction with ethyl acetate (20 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.40 g of the desired product as a yellow solid.

Melting point: 163-171 ° C
¹ H-NMR (CDCl ₃ ): δ 8.69 (d, J = 7.2Hz, 1H), 8.19 (s, 1H), 7.22 (dd, J = 7.2, 1.4Hz, 1H), 3.06 (q, J = (7.4Hz, 2H), 1.23 (t, J = 7.4Hz, 3H) (CO ₂ H proton peak could not be observed).
Intermediate Synthesis Example 2: Synthesis of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid chloride Step 1: Ethyl 3- (ethylsulfonyl) -7- Synthesis of (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate Ethyl 3- (ethylthio) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylate 7 To a mixed solution of .19 g and acetic acid 40 ml, 746 mg of sodium tungstate dihydrate and 5.64 g of 30 wt% aqueous hydrogen peroxide were sequentially added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 16 hours. The reaction mixture was then stirred at 50 ° C. for 2 hours. Further thereafter, the reaction mixture was stirred at 80 ° C. for 1 hour. After completion of the stirring, 2.82 g of 30 wt% aqueous hydrogen peroxide was added to the reaction mixture at room temperature, and the reaction mixture was stirred at 80 ° C. for 3 hours. After completion of the reaction, 30 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with chloroform (50 ml × 2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 7.07 g of the desired product as a yellow solid.

Melting point: 129-131 ° C
Step 2: Synthesis of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid 7.07 g of yellow solid obtained in Step 1, ethanol 40 ml and tetrahydrofuran 40 ml 10 ml of a 4 mol / L aqueous sodium hydroxide solution was added to the mixed solution at room temperature. After the addition was complete, the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 1 mol / L hydrochloric acid was added to the obtained residue to adjust the pH of the aqueous layer to 2, followed by extraction with chloroform (20 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 6.43 g of the desired product as a white solid.

Melting point: 158-160 ° C
Step 3: Synthesis of 3- (ethylsulfonyl) -7- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxylic acid chloride Mixing 5.36 g of the white solid obtained in Step 2 and 110 ml of dichloromethane To the solution, 5.28 g of oxalyl dichloride and 30 mg of N, N-dimethylformamide were sequentially added under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 3 hours. After completion of the stirring, the solvent was distilled off from the reaction mixture under reduced pressure. The precipitated solid was added with 20 ml of n-hexane and filtered to obtain 5.22 g of the desired product as a white solid.

Melting point: 171-175 ° C
Intermediate Synthesis Example 3: Synthesis of 2-bromo-1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one Synthesis of (S) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-ol N ² -methyl-5 To a mixed solution of 37.7 g of (trifluoromethyl) pyridine-2,3-diamine and 150 ml of pyridine, 32.8 g of (S) -1-chloro-1-oxopropan-2-yl acetate was added at −20 ° C. did. After the addition was complete, the mixture was stirred at room temperature for 30 minutes. After completion of the stirring, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 150 ml of ethanol, and 39.4 ml of a 10 mol / L aqueous sodium hydroxide solution was added at room temperature. After the addition was complete, the reaction mixture was stirred for 2 hours under heating to reflux. After completion of the stirring, 20 ml of a 10 mol / L aqueous sodium hydroxide solution was added to the reaction mixture at room temperature. After the addition was complete, the reaction mixture was stirred for 4.5 hours under heating to reflux. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. 12 mol / L hydrochloric acid was added to the obtained residue to adjust the pH of the aqueous layer to 4, and the mixture was extracted with ethyl acetate (100 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 59.8 g of the desired product as a black solid.

¹ H-NMR (CDCl ₃ ): δ 8.65 (s, 1H), 8.23 (s, 1H), 5.20 (brs, 1H), 3.97 (s, 3H), 2.99 (brs, 1H), 1.75 (d, J = 6.3Hz, 3H).
Step 2: Synthesis of 1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one Black solid 48 obtained in step 1 A mixed solution of .3 g and 200 ml of acetic acid was heated to 90 ° C., and 14.8 g of chromium (VI) oxide dissolved in 50 ml of water was added. After the addition was complete, the mixture was stirred for 1.5 hours under heating to reflux. Thereafter, 5 g of chromium (VI) oxide dissolved in 10 ml of water was added to the reaction mixture at 90 ° C., and the reaction mixture was stirred for 1.5 hours with heating under reflux. After completion of the reaction, the reaction mixture was added dropwise to 800 ml of water at room temperature. The precipitated solid was filtered. The obtained solid was washed with water to obtain 35.6 g of the desired product as a brown solid.

Melting point: 106-108 ° C
¹ H-NMR (CDCl ₃ ): δ8.82 (d, J = 1.5Hz, 1H), 8.43 (d, J = 1.5Hz, 1H), 4.23 (s, 3H), 2.86 (s, 3H).
Step 3: Synthesis of 2-bromo-1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one obtained in step 2. To a mixed solution of 17.95 g of a brown solid, 8.2 g of triethylamine, and 180 ml of dichloromethane, 17.2 g of trimethylsilyl trifluoromethanesulfonate was added under ice cooling. After completion of the addition, the mixture was stirred for 1 hour under ice cooling. After the completion of stirring, 28.7 g of trimethylphenylammonium tribromide was added to the reaction mixture under ice cooling. After completion of the addition, the reaction mixture was stirred for 30 minutes under ice cooling. After completion of the reaction, 200 ml of water was added to the reaction mixture and extracted with dichloromethane (200 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 50:50) to obtain 21.3 g of the desired product as a white solid.

Melting point: 90-91 ° C
¹ H-NMR (CDCl ₃ ): δ 8.86 (d, J = 1.8Hz, 1H), 8.47 (d, J = 1.8Hz, 1H), 4.85 (s, 2H), 4.26 (s, 3H).
Intermediate Synthesis Example 4: 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1 Step 1: Synthesis of 2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one Synthesis 2-Bromo-1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one 20 g and N, N-dimethylformamide 80 ml To the mixed solution, 4.2 g of ethanethiol and 9.4 g of potassium carbonate were sequentially added under ice cooling. After completion of the addition, the mixture was stirred for 30 minutes under ice cooling. The reaction mixture was then stirred at room temperature for 1 hour. After completion of the reaction, 100 ml of water was added to the reaction mixture and extracted with ethyl acetate (100 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 80:20) to obtain 13.8 g of the desired product as a pale yellow solid.

Melting point: 67-69 ° C
¹ H-NMR (CDCl ₃ ): δ8.85-8.80 (m, 1H), 8.45-8.40 (m, 1H), 4.24 (s, 3H), 4.07 (s, 2H), 2.66 (q, J = 7.4 Hz, 2H), 1.31 (t, J = 7.4Hz, 3H).
Step 2: 2-Bromo-2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-one Synthesis 8.8 g of trimethylsilyl trifluoromethanesulfonate was added to a mixed solution of 11.4 g of the pale yellow solid obtained in Step 1, 4.2 g of triethylamine and 100 ml of dichloromethane at −20 ° C. After completion of the addition, the reaction mixture was stirred for 20 minutes under ice cooling. After completion of the stirring, the reaction mixture was cooled to −20 ° C., and 14.1 g of trimethylphenylammonium tribromide was added. After completion of the addition, the reaction mixture was stirred for 30 minutes under ice cooling. After completion of the reaction, the reaction mixture was added dropwise to 100 ml of water under ice cooling and extracted with chloroform (100 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 13.4 g of the desired product as a red brown oil.

¹ H-NMR (CDCl ₃ ): δ8.90-8.80 (m, 1H), 8.50-8.40 (m, 1H), 7.14 (s, 1H), 4.27 (s, 3H), 3.05-2.80 (m, 2H ), 1.39 (t, J = 7.6Hz, 3H).
Intermediate synthesis example 5: (Z) -2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane- Synthesis of 1-one O-acetyl oxime Step 1: Synthesis of S-ethyl-L-cysteine 4 ml of 25 mol / L aqueous sodium hydroxide solution was added to a mixed solution of 4.0 g of L-cysteine and 100 ml of ethanol at room temperature. . After the addition was complete, the mixture was heated to 60 ° C. and 3.96 g of ethyl bromide was added. After the addition was complete, the mixture was stirred at 60 ° C. for 1 hour. After completion of the reaction, the reaction mixture was cooled to room temperature, and acetic acid was added to adjust the pH to 5. After the precipitated solid was filtered, the obtained solid was washed with 20 ml of ethanol to obtain 3.83 g of the desired product (stereoconfiguration estimated) as a white solid.
¹ H-NMR (D ₂ O): δ 3.85-3.70 (m, 1H), 3.10-2.85 (m, 2H), 2.52 (q, J = 7.2Hz, 2H), 1.15 (t, J = 7.2 Hz, 3H) (NH ₂ and CO ₂ H proton signals could not be observed).
Step 2: Synthesis of (R) -2-amino-3- (ethylthio) -N- [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] propanamide N ² -Methyl-5 To a mixed solution of 180 mg of (trifluoromethyl) pyridine-2,3-diamine, 210 mg of S-ethyl-L-cysteine synthesized by the method of Step 1, and 3 ml of toluene, 50 mg of magnesium sulfate was added at room temperature. After the addition was complete, the mixture was heated to 110 ° C. and 551 mg of sulfuric acid was added. After the addition was complete, the mixture was stirred at 110 ° C. for 11 hours. The mixture was then stirred at 130 ° C. for 9 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture at room temperature and washed with toluene (20 ml). A 1 mol / L sodium hydroxide aqueous solution was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 13 and then extracted with chloroform (20 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 236 mg of the desired product (stereo configuration estimated) as a brown oil.
¹ H-NMR (CDCl ₃ ): δ 9.20 (brs, 1H), 8.32 (d, J = 1.8Hz, 1H), 7.63 (d, J = 1.8Hz, 1H), 5.29 (brs, 1H), 3.77 (dd, J = 6.9, 4.2Hz, 1H), 3.15-2.90 (m, 2H), 3.04 (d, J = 4.8Hz, 3H), 2.70 (q, J = 7.8Hz, 2H), 1.92 (brs, 2H), 1.29 (t, J = 7.8Hz, 3H).
Step 3: (R) -2- (Ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-amine Synthesis A mixed solution of 236 mg of the brown oil obtained in Step 2 and 3 ml of acetic acid was stirred at 80 ° C. for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. The obtained residue was purified by medium pressure preparative liquid chromatography (chloroform: methanol = 10: 1) to obtain 50 mg of the desired product (stereo configuration estimated) as a yellow solid.
¹ H-NMR (CDCl ₃ ): δ8.65 (s, 1H), 8.23 (s, 1H), 4.34 (t, J = 6.8Hz, 1H), 4.00 (s, 3H), 3.21 (dd, J = 13.5, 5.7Hz, 1H), 3.03 (dd, J = 13.3, 8.1Hz, 1H), 2.56 (q, J = 7.4Hz, 2H), 1.95 (brs, 2H), 1.27 (t, J = 7.4Hz, 3H).
Step 4: Synthesis of 2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime To a mixed solution of 200 mg of the yellow solid synthesized by the method 3 and 5 ml of 1,2-dichloroethane, 43 mg of sodium tungstate dihydrate and 372 mg of 30 wt% hydrogen peroxide water were sequentially added at room temperature. After the addition was complete, the reaction mixture was stirred at 50 ° C. for 3 hours. Thereafter, 43 mg of sodium tungstate dihydrate and 186 mg of 30 wt% aqueous hydrogen peroxide were sequentially added to the reaction mixture at the same temperature, and the reaction mixture was stirred at 50 ° C. for 30 minutes. After completion of the reaction, a solution of sodium bisulfite (680 mg) in water (10 ml) was added to the reaction mixture at room temperature, followed by extraction with dichloromethane (10 ml × 3). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 15: 85-0: 100) to obtain 38 mg of the desired product as a yellow solid. The obtained target product was a mixture of two geometric isomers derived from the oxime structure, and the geometric isomer ratio was 99: 1 (geometric isomer A: geometric isomer B). The geometric isomer ratio was calculated from the integrated value of the ¹ H-NMR spectrum signal of the geometric isomer mixture.
Geometric isomer A
¹ H-NMR (DMSO-d6): ¹ H-NMR (DMSO-d6): δ 13.3 (s, 1H), 8.83 (d, J = 2.1Hz, 1H), 8.62 (d, J = 2.1Hz, 1H ), 4.86 (s, 2H), 4.04 (s, 3H), 3.24 (q, J = 7.2Hz, 2H), 1.27 (t, J = 7.2Hz, 3H).
Geometric isomer B
¹ H-NMR (DMSO-d6): δ 12.9 (s, 1H), 8.82 (d, J = 2.1Hz, 1H), 8.59 (d, J = 2.1Hz, 1H), 4.63 (s, 2H), 3.78 (s, 3H), 3.22 (q, J = 7.2Hz, 2H), 1.22 (t, J = 7.2Hz, 3H).
Step 5: (Z) -2- (Ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one Synthesis of O-acetyl oxime To a mixed solution of 145 mg of the yellow solid synthesized by the method of Step 4 and 4 ml of dichloromethane, 101 mg of triethylamine and 51 mg of acetic anhydride were sequentially added at room temperature. After the addition was complete, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with dichloromethane (20 ml). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 160 mg of the desired product as a white solid.
¹ H-NMR (CDCl ₃ ): δ8.79 (d, J = 2.1Hz, 1H), 8.33 (d, J = 2.1Hz, 1H), 5.00 (s, 2H), 4.28 (s, 3H), 3.20 (q, J = 7.2Hz, 2H), 2.37 (s, 3H), 1.48 (t, J = 7.2Hz, 3H).
Intermediate Synthesis Example 6: 2- (Ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime Step 1: Synthesis of 2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime 2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one 10.0 g, potassium acetate; 2.75 g of hydroxylamine hydrochloride was added to a mixed solution of 24 g and 55 ml of ethanol at room temperature. After the addition was complete, the mixture was stirred at room temperature for 22 hours. Furthermore, 458 mg of hydroxylamine hydrochloride was added to the reaction mixture, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. 100 ml of water was added to the obtained residue, and the mixture was extracted with ethyl acetate (50 ml × 2). The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 10.4 g of the desired product as a white solid. The obtained target product was a mixture of two geometric isomers derived from the oxime structure, and the geometric isomer ratio was 6: 4 (geometric isomer A: geometric isomer B). The geometric isomer ratio was calculated from the integrated value of the ¹ H-NMR spectrum signal of the geometric isomer mixture.
Geometric isomer A
¹ H-NMR (CDCl ₃ ): δ9.05 (brs, 1H), 8.70 (d, J = 2.1Hz, 1H), 8.32 (s, 1H), 4.09 (s, 3H), 3.95 (s, 2H) , 2.67 (q, J = 7.2Hz, 2H), 1.29 (t, J = 7.2Hz, 3H).
Geometric isomer B
¹ H-NMR (CDCl ₃ ): δ 9.35 (brs, 1H), 8.73 (d, J = 2.1Hz, 1H), 8.32 (s, 1H), 4.13 (s, 3H), 3.80 (s, 2H), 2.55 (q, J = 7.2Hz, 2H), 1.24 (t, J = 7.2Hz, 3H).
Step 2: Synthesis of 2- (ethylsulfonyl) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1-one oxime To a mixed solution of 1.15 g of the white solid obtained in 1 and 20 ml of dichloromethane, 1.8 g of 65 wt% metachloroperbenzoic acid was added under ice cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, 20 ml of a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with chloroform (20 ml × 2). The obtained organic layer was washed with a saturated aqueous solution of sodium bicarbonate, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product of the intended product. The obtained crude product of the target product was a mixture of two geometric isomers derived from the oxime structure. The crude product was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 65:35), and the two geometric isomers were separated. 519 mg (geometric isomer A) and 282 mg (geometric isomer B) were obtained as white solids, respectively.
Geometric isomer A
¹ H-NMR (DMSO-d6): δ 13.3 (s, 1H), 8.83 (d, J = 2.1Hz, 1H), 8.62 (d, J = 2.1Hz, 1H), 4.86 (s, 2H), 4.04 (s, 3H), 3.24 (q, J = 7.2Hz, 2H), 1.27 (t, J = 7.2Hz, 3H).
Geometric isomer B
¹ H-NMR (DMSO-d6): δ 12.9 (s, 1H), 8.82 (d, J = 2.1Hz, 1H), 8.59 (d, J = 2.1Hz, 1H), 4.63 (s, 2H), 3.78 (s, 3H), 3.22 (q, J = 7.2Hz, 2H), 1.22 (t, J = 7.2Hz, 3H).
Intermediate synthesis example 7: (R) -2- (ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethane-1 -Synthesis of amine Step 1: Synthesis of N-acetyl-S-ethyl-L-cysteine To a mixed solution of 450 mg of white solid obtained in Step 1 of Intermediate Synthesis Example 5 and 5 ml of 1 mol / L aqueous sodium hydroxide solution, ice Under cooling, 339 mg of acetic anhydride was added. After the addition was complete, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, concentrated hydrochloric acid was added to the reaction mixture to adjust the pH of the aqueous layer to 1-2, followed by extraction with chloroform (30 ml). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. After the precipitated solid was filtered, the obtained solid was washed with diisopropyl ether to obtain 359 mg of the desired product (stereo configuration estimated) as a white solid.
¹ H-NMR (CDCl ₃ ): δ 8.34 (brs, 1H), 6.51 (d, J = 7.0Hz, 1H), 4.85-4.75 (m, 1H), 3.05 (dd, J = 5.1, 1.8Hz, 2H), 2.65-2.50 (m, 2H), 2.10 (s, 3H), 1.26 (t, J = 7.2Hz, 3H).
Step 2: Synthesis of (R) -2-acetamido-3- (ethylthio) -N- [2- (methylamino) -5- (trifluoromethyl) pyridin-3-yl] propanamide N ² -Methyl-5 To a mixed solution of 1.92 g of (trifluoromethyl) pyridine-2,3-diamine, 2.49 g of the white solid synthesized by the method of Step 1, and 20 ml of dichloromethane, 1-ethyl-3- (3 -Dimethylaminopropyl) carbodiimide hydrochloride 2.49 g was added. After the addition was complete, the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, 30 ml of water was added to the reaction mixture, and extracted with dichloromethane (50 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 50: 50 to 20:80), and 2.17 g of the target product (configuration was estimated) was a white solid. Got as.

¹ H-NMR (CDCl ₃ ): δ 8.41 (brs, 1H), 8.30 (s, 1H), 7.70 (brs, 1H), 6.69 (brs, 1H), 5.62 (brs, 1H), 4.80-4.65 (m , 1H), 3.02 (d, J = 4.5Hz, 3H), 3.00-2.90 (m, 2H), 2.63 (q, J = 7.4Hz, 2H), 2.08 (s, 3H), 1.29 (t, J = (7.4Hz, 3H).
Step 3: (R) -N- [2- (Ethylthio) -1- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) ethyl] acetamide A mixed solution of 2.0 g of the white solid obtained in Step 2 and 10 ml of acetic acid was stirred at 80 ° C. for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. 10 ml of ethyl acetate was added to the precipitated solid, followed by filtration to obtain 1.23 g of the target product (estimated configuration) as a light yellow solid.
¹ H-NMR (CDCl ₃ ): δ8.68 (d, J = 1.5Hz, 1H), 8.22 (d, J = 1.5Hz, 1H), 6.74 (d, J = 7.4Hz, 1H), 5.57 (q , J = 7.5Hz, 1H), 4.03 (s, 3H), 3.17 (d, J = 7.0Hz, 2H), 2.50 (q, J = 7.4Hz, 2H), 2.04 (s, 3H), 1.22 (t , J = 7.4Hz, 3H).
Step 4: (R) -2- (Ethylthio) -1- [3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl] ethan-1-amine Synthesis 5 ml of 12 mol / L hydrochloric acid was added at 80 ° C. to a mixed solution of 1.13 g of light yellow solid obtained in Step 3 and 10 ml of ethanol. After the addition was complete, the mixture was stirred at 80 ° C. for 4 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. To the obtained residue, 10 ml of water was added and washed with ethyl acetate (10 ml). A 1 mol / L sodium hydroxide aqueous solution was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 10 to 11, followed by extraction with ethyl acetate (5 ml × 3). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 634 mg of the desired product (stereo configuration estimated) as a yellow solid.
¹ H-NMR (CDCl ₃ ): δ8.65 (s, 1H), 8.23 (s, 1H), 4.34 (t, J = 6.8Hz, 1H), 4.00 (s, 3H), 3.21 (dd, J = 13.5, 5.7Hz, 1H), 3.03 (dd, J = 13.3, 8.1Hz, 1H), 2.56 (q, J = 7.4Hz, 2H), 1.95 (brs, 2H), 1.27 (t, J = 7.4Hz, 3H).
Intermediate Synthesis Example 8: Synthesis of 6-bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-amine Step 1: tert-butyl [6-bromo-3- (ethylthio) imidazo [1, Synthesis of 2-a] pyridin-2-yl] carbamate 6-bromo-3- (ethylthio) synthesized according to the method described in Intermediate Synthesis Example 1 using 5-bromopyridin-2-amine as a starting material To a mixed solution of imidazo [1,2-a] pyridine-2-carboxylic acid (1.5 g) and 2-methyl-2-propanol (10 ml), 1.51 g of triethylamine and 1.64 g of diphenylphosphoryl azide were sequentially added at room temperature. did. After the addition was complete, the mixture was stirred for 2 hours under heating to reflux. After completion of the reaction, the solvent was distilled off from the reaction mixture. 20 ml of water was added to the obtained residue, and extracted with dichloromethane (20 ml × 2). The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography (gradient of n-hexane: ethyl acetate = 100: 0 to 20:80) to obtain 2.05 g of the desired product as a brown resinous substance.

¹ H-NMR (CDCl ₃ ): δ 8.44 (d, J = 2.1Hz, 1H), 7.52 (d, J = 9.3Hz, 1H), 7.31 (dd, J = 9.3, 2.1Hz, 1H), 7.01 (brs, 1H), 2.66 (q, J = 7.2Hz, 2H), 1.56 (s, 9H), 1.22 (t, J = 7.2Hz, 3H).
Step 2: Synthesis of 6-bromo-3- (ethylthio) imidazo [1,2-a] pyridin-2-amine To a mixed solution of 2.05 g of the brown resinous material obtained in Step 1 and 10 ml of dichloromethane, Below, 10 ml of trifluoroacetic acid was added. After the addition was complete, the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture. To the obtained residue, 4 ml / L hydrochloric acid (10 ml) was added and washed with ethyl acetate (10 ml × 2). A 10 mol / L aqueous sodium hydroxide solution was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 9, followed by extraction with chloroform (10 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 990 mg of the desired product as a brown solid.

Melting point: 88-92 ° C
Compound (1) is a known compound described in International Patent Application No. 2016/129684, and specific examples thereof include compounds shown in Tables 1 to 3. However, the condensed heterocyclic compound used as the first active ingredient of the composition of the present invention is not limited to these.

In the table, “Et” represents ethyl and “Me” represents methyl. In the table, “mp” represents a melting point (unit: ° C.).
[Table 1]

――――――――――――――――――――――――――――――
No. R ³ Y2 Y3 Y4 mp
――――――――――――――――――――――――――――――
1-001 CF ₃ Cl HH 217-218
1-002 CF ₃ Br HH 205-207
1-003 CF ₃ IHH 215-218
1-004 CF ₃ CF ₃ HH 212-213
1-005 CF ₃ H Cl H 214-215
1-006 CF ₃ HIH 208-211
1-007 CF ₃ IH CN 253-256
1-008 CF ₃ CF ₃ HF 195-196
1-009 SOCF ₃ H CF ₃ H 218-219
――――――――――――――――――――――――――――――
[Table 2]

――――――――――――――――――――――――――――――
No. R ³ Y2 Y3 Y4 mp
――――――――――――――――――――――――――――――
2-001 CF ₃ H CF ₃ H 245-247
――――――――――――――――――――――――――――――
[Table 3]

――――――――――――――――――――――――――――――
No. R ³ Y2 Y3 Y4 mp
――――――――――――――――――――――――――――――
3-001 CF ₃ Br HH 250-255
――――――――――――――――――――――――――――――
The compound contained in the active compound II which is the second active ingredient of the composition of the present invention is known as a compound having insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal activity, Are selected from the active ingredient groups BI to B-XXVI. Specific examples thereof are shown in the following Tables 4 to 29 together with Compound Nos. These compounds tend to increase the amount of sprayed medicine and the number of spraying due to the emergence of resistant pests or resistant bacteria, and the lack of insecticidal sterilization spectrum and residual effects. There are also cases where improvement is required from the aspect of environmental safety, such as an increase in the risk to aquatic organisms.
Active ingredient group BI
[Table 4]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
A01 Metalaxyl-M
A02 Hymexazol
―――――――――――――――――――――――――――――――――――
Active ingredient group B-II
[Table 5]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
B01 benomyl
B02 Thiophanate-methyl
B03 Diethofencarb
B04 ethaboxam
B05 Zoxamide
B06 Pencicuron
B07 fluopicolide
―――――――――――――――――――――――――――――――――――
Active ingredient group B-III
[Table 6]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
C01 Benzovindiflupyr
C02 Bixafen
C03 Boscalid
C04 fluopyram
C05 Flutolanil
C06 Fluxapyroxad
C07 Furametpyr
C08 Isofetamid
C09 Isopyrazam
C10 mepronil
C11 penflufen
C12 penthiopyrad
C13 sedaxane
C14 thifluzamide
C15 Azoxystrobin
C16 coumoxystrobin
C17 dimoxystrobin
C18 enestrobin
C19 enoxastrobin
C20 Famoxadone
C21 fenamidone
C22 phenaminstrobin
C23 flufenoxystrobin
C24 fluoxastrobin
C25 kresoxim-methyl
C26 mandestrobin
C27 Metominostrobin
C28 orysastrobin
C29 picoxystrobin
C30 pyraclostrobin
C31 pyrametostrobin
C32 pyraoxystrobin
C33 pyribencarb-methyl
C34 pyriminostrobin
C35 triclopyricab
C36 Trifloxystrobin
C37 amisulbrom
C38 cyazofamid
C39 fluazinam
C40 Ametoctrazine
C41 pydiflumetofen
C42 pyraziflumid
C43 full indapir (fluindapyr)
C44 inpyrfluxam
C45 isoflucypram
C46 fenpicoxamid
―――――――――――――――――――――――――――――――――――
Active ingredient group B-IV
[Table 7]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
D01 Mepanipyrim
D02 kasugamycin
―――――――――――――――――――――――――――――――――――
Active ingredient group BV
[Table 8]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
E01 Quinoxyfen
E02 Fludioxonil
―――――――――――――――――――――――――――――――――――
Active ingredient group B-VI
[Table 9]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
F01 iprodione
F02 Procymidone
―――――――――――――――――――――――――――――――――――
Active ingredient group B-VII
[Table 10]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
G01 tolclofos-methyl
G02 Bacillus subtilis,
Strain: D747, FZB24, GBO3, HAI0404, MBI600, QST713, Y1336, etc.)
―――――――――――――――――――――――――――――――――――
Active ingredient group B-VIII
[Table 11]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
H01 Bromuconazole
H02 Cyproconazole
H03 Difenoconazole
H04 Diniconazole-M
H05 Epoxiconazole
H06 Fenarimol
H07 Fenbuconazole
H08 fluquinconazole
H09 hexaconazole
H10 Imazalil
H11 imibenconazole
H12 ipconazole
H13 metconazole
H14 myclobutanil
H15 penconazole
H16 prochloraz
H17 propiconazole
H18 prothioconazole
H19 simeconazole
H20 tebuconazole
H21 tetraconazole
H22 Triflumizole
H23 Fenpropidin
H24 Fenhexamid
H25 Fenpyrazamine
H26 ipfentrifluconazole
H27 mefentrifluconazole
―――――――――――――――――――――――――――――――――――
Active ingredient group B-IX
[Table 12]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
I01 Validamycin
I02 Polyoxins
I03 Polyoxin-D (polyoxorim)
I04 Benthiavalicarb-isopropyl
I05 Dimethomorph
I06 iprovalicarb
I07 mandipropamid
―――――――――――――――――――――――――――――――――――
Active ingredient group BX
[Table 13]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
J01 phthalide
J02 tricyclazole
J03 Carpropamid
J04 diclocymet
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XI
[Table 14]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
K01 Acibenzolar-S-methyl
K02 probenazole
K03 Isotianil
K04 Diclobentiazox
K05 Thiadinil
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XII
[Table 15]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
L01 Bordeaux mixture
L02 Copper carbonate, basic
L03 Copper hydroxide
L04 Copper naphthenate
L05 Copper oleate
L06 Basic oxychloride
L07 copper sulfate
L08 Copper sulfate, basic
L09 oxine copper
L10 calcium polysulfide
L11 sulfur
L12 mancozeb
L13 maneb
L14 polycarbamate
L15 propineb
L16 captan
L17 folpet
L18 chlorothalonil
L19 iminoctadine-albesilate
L20 iminoctadine-triacetate
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XIII
[Table 16]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
M01 Cyflufenamid
M02 Simoxanil
M03 flusulfamide
M04 Flutianil
M05 Fosetyl-aluminium
M06 metrafenone
M07 Oxathiapiprolin
M08 Pyriophenone
M09 Picarbutrazox
M10 dipymetitrone
M11 quinofumelin
M12 Lipopeptide
M13 Phosphorous acid
M14 BCF-082 (test name)
M15 NF-180 (test name)
M16 S-2399 (test name)
M17 AKD-5195 (test name)
M18 S-2190 (test name)
M19 aminopyrifen
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XIV
[Table 17]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
N01 Acephate
N02 Cadusafos
N03 Chlorpyrifos
N04 Diazinon
N05 Dichlorvos
N06 Dimethoate
N07 EPN (EPN)
N08 Malathion
N09 Methamidophos
N10 Parathion-methyl
N12 Phenthoate
N13 Phorate
N14 Phosmet
N15 Phoxim
N16 Profenofos
N17 Terbufos
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XV
[Table 18]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
O01 Aldicarb
O02 Benfuracarb
O03 Carbaryl
O04 Carbofuran
O05 Carbosulfan
O06 Methomyl
O07 Pirimicarb
O08 Thiodicarb
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XVI
[Table 19]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
P01 Acrinathrin
P02 Bifenthrin
P03 Cyfluthrin
P04 Cypermethrin
P05 Deltamethrin
P06 Esfenvalerate
P07 Etofenprox
P08 Permethrin
P09 Tefluthrin
P10 Lambda-Cyhalothrin
P11 tau-Fluvalinate
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XVII
[Table 20]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
Q01 Bensultap
Q02 Cartap hydrochloride
Q03 Thiocyclam
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XVIII
[Table 21]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
R01 Acetamiprid
R02 Clothianidin
R03 Dinotefuran
R04 Imidacloprid
R05 Nitenpyram
R06 Thiacloprid
R07 Thiamethoxam
R08 Sulfoxaflor
R09 Flupyradifurone
R10 Triflumezopyrim
R11 Dicloromezotiaz
R12 flupyrimin
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XIX
[Table 22]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
S01 Spinetoram
S02 Spinosad
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XX
[Table 23]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
T01 Ethiprole
T02 Fipronil
T03 Broflanilide
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXI
[Table 24]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
U01 Abamectin
U02 Emamectin benzoate
U03 Lepimectin
U04 Milbemectin
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXII
[Table 25]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
V01 Chlorantraniliprole
V02 Cyantraniliprole
V03 Flubendiamide
V04 Cyclaniliprole
V05 Tetraniliprole
V06 Cyhalodiamide
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXIII
[Table 26]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
W01 Diafenthiuron
W02 Fenpyroximate
W03 Pyridaben
W04 Torfenpyrad
W05 Cyenopyrafen
W06 Cyflumetofen
W07 Pyflubumide
W08 Hydramethylnon
W09 Acequinocyl
W10 Chlorfenapyr
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXIV
[Table 27]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
X01 Pyriproxyfen
X02 Methoxyfenozide
X03 Diflubenzuron
X04 Flufenoxuron
X05 Lufenuron
X06 Novaluron
X07 Teflubenzuron
X08 Buprofezin
X09 Hexathiazox
X10 Etoxazole
X11 benzpyrimoxan
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXV
[Table 28]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
Y01 Bacillus thuringensis
Y02 Bacillus sphaericus
―――――――――――――――――――――――――――――――――――
Active ingredient group B-XXVI
[Table 29]
―――――――――――――――――――――――――――――――――――
No. Compound name (generic name)
―――――――――――――――――――――――――――――――――――
Z01 Pymetrozine
Z02 Pyrifluquinazon
Z03 aphidopyropen
Z04 Flonicamid
Z05 Spirodiclofen
Z06 Spiromesifen
Z07 Spirotetramat
Z08 Indoxacarb
Z09 Metaflumizone
Z10 Cyromazine
Z11 Azadirachtin
Z12 Pyridalyl
Z13 Bifenazate
Z14 Fluxametamide
Z15 Metaldehyde
Z16 ME-5382 (Exam name)
Z17 NA-89 (Exam name)
Z18 NNI-1501 (Exam name)
Z19 BAI-1602 (Exam name)
Z20 DKN-2601 (test name)
Z21 DAI-1601 (Exam name)
Z22 Asinonapyr (acynonapyr)
Z23 spiropidion
―――――――――――――――――――――――――――――――――――
Next, examples of combinations of active compound I which is the first active ingredient of the composition of the present invention and active compound II which is the second active ingredient are listed below. In the following notation, for example, “1-001 + (A01)” indicates that the active compound I is the compound No.1-001 in Table 1 and the active compound II is the metalaxyl No.A01 in Table 4. -M (metalaxyl-M) represents a combination.

Examples of compound combinations:
"1-001 + (A01)", "1-001 + (A02)", "1-001 + (B01)", "1-001 + (B02)", "1-001 + (B03)", "1-001 + (B04)", "1-001 + (B05)", "1-001 + (B06)", "1-001 + (B07)", "1-001 + (C01)""1-001 + (C02)", "1-001 + (C03)", "1-001 + (C04)", "1-001 + (C05)", "1-001 + (C06)", "1-001 + (C07)", "1-001 + (C08)", "1-001 + (C09)", "1-001 + (C10)", "1-001 + (C11)", “1-001 + (C12)”, “1-001 + (C13)”, “1-001 + (C14)”, “1-001 + (C15)”, “1-001 + (C16)”, “1-001 + (C17)”, “1-001 + (C18)”, “1-001 + (C19)”, “1-001 + (C20)”, “1-001 + (C21)”, "1-001 + (C22)", "1-001 + (C23)", "1-001 + (C24)", "1-001 + (C25)", "1-001 + (C26)", “1-001 + (C27)”, “1-001 + (C28)”, “1-001 + (C29)”, “1-001 + (C30)”, “1-001 + (C31)”, "1-001 + (C32)", "1-001 + (C33)", "1-001 + (C34)", "1-001 + (C35)", "1-001 + (C36)", “1-001 + (C37)”, “1-001 + (C38)”, “1-001 + (C39)”, “1-001 + (C40)”, “1-001 + (C41)”, “1-001 + (C42)”, “1-001 + (C43)”, “1-001 + (C44)”, “1-001 + (C45)”, “1-001 + (C46)”, "1-001 + (D01)", "1-001 + (D02)", "1-001 + (E01)", "1-001 + (E02)", "1-001 + (F01)", "1-001 + (F02)", "1-001 + (G01)", "1-001 + (G02)", "1-001 + (H01)", "1-001 + (H02)", "1-001 + (H03)", "1-001 + (H04)", "1-001 + (H05)", "1-001 + (H06)", "1-001 + (H07)", "1-001 + (H08)", "1-001 + (H09)", "1-001 + (H10)", "1-001 + (H11)", "1-001 + (H12)", "1-001 + (H13)", "1-001 + (H14)", "1-001 + (H15)", "1-001 + (H16)", "1-001 + (H17)", "1-001 + (H18)", "1-001 + (H19)", "1-001 + (H20)", "1-001 + (H21)", "1-001 + (H22)", "1-001 + (H23)", "1-001 + (H24)", "1-001 + (H25)", "1-001 + (H26)", "1-001 + (H27)", "1-001 + (I01)", "1-001 + (I02)", "1-001 + (I03)", "1-001 + (I04)", "1-001 + (I05)", "1-001 + (I06)", "1-001 + (I07)", "1-001 + (J01)", "1-001 + (J02)", "1-001 + (J03)", "1-001 + (J04)", "1-001 + (K01)", "1-001 + (K02)", "1-001 + (K03)", "1-001 + (K04)", "1-001 + (K05)", "1-001 + (L01)", "1-001 + (L02)", "1-001 + (L03)", "1-001 + (L04)", "1-001 + (L05)", "1-001 + (L06)", "1-001 + (L07)", "1-001 + (L08)", "1-001 + (L09)""1-001 + (L10)", "1-001 + (L11)", "1-001 + (L12)", "1-001 + (L13)", "1-001 + (L14)", “1-001 + (L15)”, “1-001 + (L16)”, “1-001 + (L17)”, “1-001 + (L18)”, “1-001 + (L19)”, “1-001 + (L20)”, “1-001 + (M01)”, “1-001 + (M02)”, “1-001 + (M03)”, “1-001 + (M04)”, "1-001 + (M05)", "1-001 + (M06)", "1-001 + (M07)", "1-001 + (M08)", "1-001 + (M09)""1-001 + (M10)", "1-001 + (M11)", "1-001 + (M12)", "1-001 + (M13)", "1-001 + (M14)", “1-001 + (M15)”, “1-001 + (M16)”, “1-001 + (M17)”, “1-001 + (M18)”, “1-001 + (M19)”, "1-001 + (N01)", "1-001 + (N02)", "1-001 + (N03)", "1-001 + (N07)", "1-001 + (N08)", “1-001 + (N12)”, “1-001 + (O03)”, “1-001 + (O05)”, “1-001 + (P02)”, “1-001 + (P03)”, “1-001 + (P04)”, “1-001 + (P07)”, “1-001 + (P10)”, “1-001 + (Q02)”, “1-001 + (R01)”, "1-001 + (R02)", "1-001 + (R03)", "1-001 + (R04)", "1-001 + (R05)", "1-001 + (R06)", "1-001 + (R07)", "1-001 + (R08)", "1-001 + (R09)", "1-001 + (R10)", "1-001 + (R11)", "1-001 + (R12)", "1-001 + (S01)", "1-001 + (S02)", "1-001 + (T01)", "1-001 + (T02)", "1-001 + (T03)", "1-001 + (U01)", "1-001 + (U02)", "1-001 + (U03)", "1-001 + (V01)", "1-001 + (V02)", "1-001 + (V03)", "1-001 + (V04)", "1-001 + (V05)", "1-001 + (V06)", "1-001 + (W03)", "1-001 + (W04)", "1-001 + (W05)", "1-001 + (W09)", "1-001 + (W10)", "1-001 + (X01)", "1-001 + (X02)", "1-001 + (X04)", "1-001 + (X05)", "1-001 + (X08)", “1-001 + (X10)”, “1-001 + (X11)”, “1-001 + (Y01)”, “1-001 + (Z01)”, “1-001 + (Z02)”, “1-001 + (Z03)”, “1-001 + (Z04)”, “1-001 + (Z05)”, “1-001 + (Z06)”, “1-001 + (Z07)”, “1-001 + (Z08)”, “1-001 + (Z09)”, “1-001 + (Z10)”, “1-001 + (Z12)”, “1-001 + (Z13)”, “1-001 + (Z14)”, “1-001 + (Z15)”, “1-001 + (Z16)”, “1-001 + (Z17)”, “1-001 + (Z18)”, "1-001 + (Z19)", "1-001 + (Z20)", "1-001 + (Z21)", "1-002 + (A01)", "1-002 + (A02)", "1-002 + (B01)", "1-002 + (B02)", "1-002 + (B03)", "1-002 + (B04)", "1-002 + (B05)""1-002 + (B06)", "1-002 + (B07)", "1-002 + (C01)", "1-002 + (C02)", "1-002 + (C03)", "1-002 + (C04)", "1-002 + (C05)", "1-002 + (C06)", "1-002 + (C07)", "1-002 + (C08)""1-002 + (C09)", "1-002 + (C10)", "1-002 + (C11)", "1-002 + (C12)", "1-002 + (C13)", "1-002 + (C14)", "1-002 + (C15)", "1-002 + (C16)", "1-002 + (C17)", "1-002 + (C18)", "1-002 + (C19)", "1-002 + (C20)", "1-002 + (C21)", "1-002 + (C22)", "1-002 + (C23)", "1-002 + (C24)", "1-002 + (C25)", "1-002 + (C26)", "1-002 + (C27)", "1-002 + (C28)", "1-002 + (C29)", "1-002 + (C30)", "1-002 + (C31)", "1-002 + (C32)", "1-002 + (C33)", "1-002 + (C34)", "1-002 + (C35)", "1-002 + (C36)", "1-002 + (C37)", "1-002 + (C38)", "1-002 + (C39)", "1-002 + (C40)", "1-002 + (C41)", "1-002 + (C42)", "1-002 + (C43)", "1-002 + (C44)", "1-002 + (C45)", "1-002 + (C46)", "1-002 + (D01)", "1-002 + (D02)", "1-002 + (E01)", "1-002 + (E02)", "1-002 + (F01)", "1-002 + (F02)", "1-002 + (G01)""1-002 + (G02)", "1-002 + (H01)", "1-002 + (H02)", "1-002 + (H03)", "1-002 + (H04)", “1-002 + (H05)”, “1-002 + (H06)”, “1-002 + (H07)”, “1-002 + (H08)”, “1-002 + (H09)”, “1-002 + (H10)”, “1-002 + (H11)”, “1-002 + (H12)”, “1-002 + (H13)”, “1-002 + (H14)”, "1-002 + (H15)", "1-002 + (H16)", "1-002 + (H17)", "1-002 + (H18)", "1-002 + (H19)", "1-002 + (H20)", "1-002 + (H21)", "1-002 + (H22)", "1-002 + (H23)", "1-002 + (H24)", "1-002 + (H25)", "1-002 + (H26)", "1-002 + (H27)", "1-002 + (I01)", "1-002 + (I02)", "1-002 + (I03)", "1-002 + (I04)", "1-002 + (I05)", "1-002 + (I06)", "1-002 + (I07)", "1-002 + (J01)", "1-002 + (J02)", "1-002 + (J03)", "1-002 + (J04)", "1-002 + (K01)", “1-002 + (K02)”, “1-002 + (K03)”, “1-002 + (K04)”, “1-002 + (K05)”, “1-002 + (L01)”, "1-002 + (L02)", "1-002 + (L03)", "1-002 + (L04)", "1-002 + (L05)", "1-002 + (L06)", "1-002 + (L07)", "1-002 + (L08)", "1-002 + (L09)", "1-002 + (L10)", "1-002 + (L11)", "1-002 + (L12)", "1-002 + (L13)", "1-002 + (L14)", "1-002 + (L15)", "1-002 + (L16)", “1-002 + (L17)”, “1-002 + (L18)”, “1-002 + (L19)”, “1-002 + (L20)”, “1-002 + (M01)”, "1-002 + (M02)", "1-002 + (M03)", "1-002 + (M04)", "1-002 + (M05)", "1-002 + (M06)", "1-002 + (M07)", "1-002 + (M08)", "1-002 + (M09)", "1-002 + (M10)", "1-002 + (M11)", "1-002 + (M12)", "1-002 + (M13)", "1-002 + (M14)", "1-002 + (M15)", "1-002 + (M16)", "1-002 + (M17)", "1-002 + (M18)", "1-002 + (M19)", "1-002 + (N01)", "1-002 + (N02)", "1-002 + (N03)", "1-002 + (N07)", "1-002 + (N08)", "1-002 + (N12)", "1-002 + (O03)", “1-002 + (O05)”, “1-002 + (P02)”, “1-002 + (P03)”, “1-002 + (P04)”, “1-002 + (P07)”, “1-002 + (P10)”, “1-002 + (Q02)”, “1-002 + (R01)”, “1-002 + (R02)”, “1-002 + (R03)”, "1-002 + (R04)", "1-002 + (R05)", "1-002 + (R06)", "1-002 + (R07)", "1-002 + (R08)", "1-002 + (R09)", "1-002 + (R10)", "1-002 + (R11)", "1-002 + (R12)", "1-002 + (S01)", "1-002 + (S02)", "1-002 + (T01)", "1-002 + (T02)", "1-002 + (T03)", "1-002 + (U01)""1-002 + (U02)", "1-002 + (U03)", "1-002 + (V01)", "1-002 + (V02)", "1-002 + (V03)", "1-002 + (V04)", "1-002 + (V05)", "1-002 + (V06)", "1-002 + (W03)", "1-002 + (W04)", “1-002 + (W05)”, “1-002 + (W09)”, “1-002 + (W10)”, “1-002 + (X01)”, “1-002 + (X02)”, "1-002 + (X04)", "1-002 + (X05)", "1-002 + (X08)", "1-002 + (X10)", "1-002 + (X11)", "1-002 + (Y01)", "1-002 + (Z01)", "1-002 + (Z02)", "1-002 + (Z03)", "1-002 + (Z04)", "1-002 + (Z05)", "1-002 + (Z06)", "1-002 + (Z07)", "1-002 + (Z08)", "1-002 + (Z09)", "1-002 + (Z10)", "1-002 + (Z12)", "1-002 + (Z13)", "1-002 + (Z14)", "1-002 + (Z15)", “1-002 + (Z16)”, “1-002 + (Z17)”, “1-002 + (Z18)”, “1-002 + (Z19)”, “1-002 + (Z20)”, "1-002 + (Z21)", "1-003 + (A01)", "1-003 + (A02)", "1-003 + (B01)", "1-003 + (B02)", "1-003 + (B03)", "1-003 + (B04)", "1-003 + (B05)", "1-003 + (B06)", "1-003 + (B07)""1-003 + (C01)", "1-003 + (C02)", "1-003 + (C03)", "1-003 + (C04)", "1-003 + (C05)", "1-003 + (C06)", "1-003 + (C07)", "1-003 + (C08)", "1-003 + (C09)", "1-003 + (C10)""1-003 + (C11)", "1-003 + (C12)", "1-003 + (C13)", "1-003 + (C14)", "1-003 + (C15)", "1-003 + (C16)", "1-003 + (C17)", "1-003 + (C18)", "1-003 + (C19)", "1-003 + (C20)", "1-003 + (C21)", "1-003 + (C22)", "1-003 + (C23)", "1-003 + (C24)", "1-003 + (C25)", "1-003 + (C26)", "1-003 + (C27)", "1-003 + (C28)", "1-003 + (C29)", "1-003 + (C30)", "1-003 + (C31)", "1-003 + (C32)", "1-003 + (C33)", "1-003 + (C34)", "1-003 + (C35)", 1-003 + (C36), 1-003 + (C37), 1-003 + (C38), 1-003 + (C39), 1-003 + (C40), “1-003 + (C41)”, “1-003 + (C42)”, “1-003 + (C43)”, “1-003 + (C44)”, “1-003 + (C45)”, “1-003 + (C46)”, “1-003 + (D01)”, “1-003 + (D02)”, “1-003 + (E01)”, “1-003 + (E02)”, "1-003 + (F01)", "1-003 + (F02)", "1-003 + (G01)", "1-003 + (G02)", "1-003 + (H01)", "1-003 + (H02)", "1-003 + (H03)", "1-003 + (H04)", "1-003 + (H05)", "1-003 + (H06)", "1-003 + (H07)", "1-003 + (H08)", "1-003 + (H09)", "1-003 + (H10)", "1-003 + (H11)", "1-003 + (H12)", "1-003 + (H13)", "1-003 + (H14)", "1-003 + (H15)", "1-003 + (H16)", "1-003 + (H17)", "1-003 + (H18)", "1-003 + (H19)", "1-003 + (H20)", "1-003 + (H21)", "1-003 + (H22)", "1-003 + (H23)", "1-003 + (H24)", "1-003 + (H25)", "1-003 + (H26)", "1-003 + (H27)", "1-003 + (I01)", "1-003 + (I02)", "1-003 + (I03)", "1-003 + (I04)", "1-003 + (I05)", "1-003 + (I06)", "1-003 + (I07)", "1-003 + (J01)", "1-003 + (J02)", "1-003 + (J03)", "1-003 + (J04)", "1-003 + (K01)", "1-003 + (K02)", "1-003 + (K03)", "1-003 + (K04)", "1-003 + (K05)", "1-003 + (L01)", "1-003 + (L02)", "1-003 + (L03)", “1-003 + (L04)”, “1-003 + (L05)”, “1-003 + (L06)”, “1-003 + (L07)”, “1-003 + (L08)”, "1-003 + (L09)", "1-003 + (L10)", "1-003 + (L11)", "1-003 + (L12)", "1-003 + (L13)", "1-003 + (L14)", "1-003 + (L15)", "1-003 + (L16)", "1-003 + (L17)", "1-003 + (L18)", "1-003 + (L19)", "1-003 + (L20)", "1-003 + (M01)", "1-003 + (M02)", "1-003 + (M03)", "1-003 + (M04)", "1-003 + (M05)", "1-003 + (M06)", "1-003 + (M07)", "1-003 + (M08)", "1-003 + (M09)", "1-003 + (M10)", "1-003 + (M11)", "1-003 + (M12)", "1-003 + (M13)", "1-003 + (M14)", "1-003 + (M15)", "1-003 + (M16)", "1-003 + (M17)", "1-003 + (M18)", "1-003 + (M19)", "1-003 + (N01)", "1-003 + (N02)", "1-003 + (N03)", "1-003 + (N07)", “1-003 + (N08)”, “1-003 + (N12)”, “1-003 + (O03)”, “1-003 + (O05)”, “1-003 + (P02)”, “1-003 + (P03)”, “1-003 + (P04)”, “1-003 + (P07)”, “1-003 + (P10)”, “1-003 + (Q02)”, "1-003 + (R01)", "1-003 + (R02)", "1-003 + (R03)", "1-003 + (R04)", "1-003 + (R05)", “1-003 + (R06)”, “1-003 + (R07)”, “1-003
+ (R08), 1-003 + (R09), 1-003 + (R10), 1-003 + (R11), 1-003 + (R12), 1-003 + (S01), 1-003 + (S02), 1-003 + (T01), 1-003 + (T02), 1-003 + (T03), 1-003 + (U01), 1-003 + (U02), 1-003 + (U03), 1-003 + (V01), 1-003 + (V02), 1-003 + (V03), 1-003 + (V04), 1-003 + (V05), 1-003 + (V06), 1-003 + (W03), 1-003 + (W04), 1-003 + (W05), 1-003 + (W09), 1-003 + (W10), 1-003 + (X01), 1-003 + (X02), 1-003 + (X04), 1-003 + (X05), 1-003 + (X08), 1-003 + (X10), 1-003 + (X11), 1-003 + (Y01), 1-003 + (Z01), 1-003 + (Z02), 1-003 + (Z03), 1-003 + (Z04), 1-003 + (Z05), 1-003 + (Z06), 1-003 + (Z07), 1-003 + (Z08), 1-003 + (Z09), 1-003 + (Z10), 1-003 + (Z12), 1-003 + (Z13), 1-003 + (Z14), 1-003 + (Z15), 1-003 + (Z16), 1-003 + (Z17), 1-003 + (Z18), 1-003 + (Z19), 1-003 + (Z20), 1-003 + (Z21), 1-004 + (A01), 1-004 + (A02), 1-004 + (B01), 1-004 + (B02), 1-004 + (B03), 1-004 + (B04), 1-004 + (B05), 1-004 + (B06), 1-004 + (B07), 1-004 + (C01), 1-004 + (C02), 1-004 + (C03), 1-004 + (C04), 1-004 + (C05), 1-004 + (C06), 1-004 + (C07), 1-004 + (C08), 1-004 + (C09), 1-004 + (C10), 1-004 + (C11), 1-004 + (C12), 1-004 + (C13), 1-004 + (C14), 1-004 + (C15), 1-004 + (C16), 1-004 + (C17), 1-004 + (C18), 1-004 + (C19), 1-004 + (C20), 1-004 + (C21), 1-004 + (C22), 1-004 + (C23), 1-004 + (C24), 1-004 + (C25), 1-004 + (C26), 1-004 + (C27), 1-004 + (C28), 1-004 + (C29), 1-004 + (C30), 1-004 + (C31), 1-004 + (C32), 1-004 + (C33), 1-004 + (C34), 1-004 + (C35), 1-004 + (C36), 1-004 + (C37), 1-004 + (C38), 1-004 + (C39), 1-004 + (C40), 1-004 + (C41), 1-004 + (C42), 1-004 + (C43), 1-004 + (C44), 1-004 + (C45), 1-004 + (C46), 1-004 + (D01), 1-004 + (D02), 1-004 + (E01), 1-004 + (E02), 1-004 + (F01), 1-004 + (F02), 1-004 + (G01), 1-004 + (G02), 1-004 + (H01), 1-004 + (H02), 1-004 + (H03), 1-004 + (H04), 1-004 + (H05), 1-004 + (H06), 1-004 + (H07), 1-004 + (H08), 1-004 + (H09), 1-004 + (H10), 1-004 + (H11), 1-004 + (H12), 1-004 + (H13), 1-004 + (H14), 1-004 + (H15), 1-004 + (H16), 1-004 + (H17), 1-004 + (H18), 1-004 + (H19), 1-004 + (H20), 1-004 + (H21), 1-004 + (H22), 1-004 + (H23), 1-004 + (H24), 1-004 + (H25), 1-004 + (H26), 1-004 + (H27), 1-004 + (I01), 1-004 + (I02), 1-004 + (I03), 1-004 + (I04), 1-004 + (I05), 1-004 + (I06), 1-004 + (I07), 1-004 + (J01), 1-004 + (J02), 1-004 + (J03), 1-004 + (J04), 1-004 + (K01), 1-004 + (K02), 1-004 + (K03), 1-004 + (K04), 1-004 + (K05), 1-004 + (L01), 1-004 + (L02), 1-004 + (L03), 1-004 + (L04), 1-004 + (L05), 1-004 + (L06), 1-004 + (L07), 1-004 + (L08), 1-004 + (L09), 1-004 + (L10), 1-004 + (L11), 1-004 + (L12), 1-004 + (L13), 1-004 + (L14), 1-004 + (L15), 1-004 + (L16), 1-004 + (L17), 1-004 + (L18), 1-004 + (L19), 1-004 + (L20), 1-004 + (M01), 1-004 + (M02), 1-004 + (M03), 1-004 + (M04), 1-004 + (M05), 1-004 + (M06), 1-004 + (M07), 1-004 + (M08), 1-004 + (M09), 1-004 + (M10), 1-004 + (M11), 1-004 + (M12), 1-004 + (M13), 1-004 + (M14), 1-004 + (M15), 1-004 + (M16), 1-004 + (M17), 1-004 + (M18), 1-004 + (M19), 1-004 + (N01), 1-004 + (N02), 1-004 + (N03), 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"1-007 + (W05)", "1-007 + (W09)", "1-007 + (W10)", "1-007 + (X01)", "1-007 + (X02)" , "1-007 + (X04)", "1-007 + (X05)", "1-007 + (X08)", "1-007 + (X10)", "1-007 + (X11)" , "1-007 + (Y01)", "1-007 + (Z01)", "1-007 + (Z02)", "1-007 + (Z03)", "1-007 + (Z04)" , "1-007 + (Z05)", "1-007 + (Z06)", "1-007 + (Z07)", "1-007 + (Z08)", "1-007 + (Z09)" , "1-007 + (Z10)", "1-007 + (Z12)", "1-007 + (Z13)", "1-007 + (Z14)", "1-007 + (Z15)" , "1-007 + (Z16)", "1-007 + (Z17)", "1-007 + (Z18)", "1-007 + (Z19)", "1-007 + (Z20)" , "1-007 + (Z21)", "1-008 + (A01)", "1-008 + (A02)", "1-008 + (B01)", "1-008 + (B02)" , "1-008 + (B03)", "1-008 + (B04)", "1-008 + (B05)", "1-008 + (B06)", "1-008 + (B07)" , "1-008 + (C01)", "1-008 + (C02)", "1-008 + (C03)", "1-008 + (C04)", "1-008 + (C05)" , "1-008 + (C06)", "1-008 + (C07)", "1-008 + (C08)", "1-008 + (C09)", "1-008 + (C10)" , "1-008 + (C11)", "1-008 + (C12)", "1-008 + (C13)", "1-008 + (C14)", "1-008 + (C15)" , "1-008 + (C16)", "1-008 + (C17)", "1-008 + (C18)", "1-008 + (C19)", "1-008 + (C20)" , "1-008 + (C21)", "1-008 + (C22)", "1-008 + (C23)", "1-008 + (C24)", "1-008 + (C25)" , "1-008 + (C26)", "1-008 + (C27)", "1-008 + (C28)", "1-008 + (C29)", "1-008 + (C30)" , "1-008 + (C31)", "1-008 + (C32)", "1-008 + (C33)", "1-008 + (C34)", "1-008 + (C35)" , "1-008 + (C36)", "1-008 + (C37)", "1-008 + (C38)", "1-008 + (C39)", "1-008 + (C40)" , "1-008 + (C41)", "1-008 + (C42)", "1-008 + (C43)", "1-008 + (C44)", "1-008 + (C45)" , "1-008 + (C46)", "1-008 + (D01)", "1-008 + (D02)", "1-008 + (E01)", "1-008 + (E02)" , "1-008 + (F01)", "1-008 + (F02)", "1-008 + (G01)", "1-008 + (G02)", "1-008 + (H01)" , "1-008 + (H02)", "1-008 + (H03)", "1-008 + (H04)", "1-008 + (H05)", "1-008 + (H06)" , "1-008 + (H07)", "1-008 + (H08)", "1-008 + (H09)", "1-008 + (H10)", "1-008 + (H11)" , "1-008 + (H12)", "1-008 + (H13)", "1-008 + (H14)", "1-008 + (H15)", "1-008 + (H16)" , "1-008 + (H17)", "1-008 + (H18)", "1-008 + (H19)", "1-008 + (H20)", "1-008 + (H21)" , "1-008 + (H22)", "1-008 + (H23)", "1-008 + (H24)", "1-008 + (H25)", "1-008 + (H26)" , "1-008 + (H27)", "1-008 + (I01)", "1-008 + (I02)", "1-008 + (I03)", "1-008 + (I04)" , "1-008 + (I05)", "1-008 + (I06)", "1-008 + (I07)", "1-008 + (J01)", "1-008 + (J02)" , "1-008 + (J03)", "1-008 + (J04)", "1-008 + (K01)", "1-008 + (K02)", "1-008 + (K03)" , "1-008 + (K04)", "1-008 + (K05)", "1-008 + (L01)", "1-008 + (L02)", "1-008 + (L03)" , "1-008 + (L04)", "1-008 + (L05)", "1-008 + (L06)", "1-008 + (L07)", "1-008 + (L08)" , "1-008 + (L09)", "1-008 + (L10)", "1-008 + (L11)", "1-008 + (L12)", "1-008 + (L13)" , "1-008 + (L14)", "1-008 + (L15)", "1-008 + (L16)", "1-008 + (L17)", "1-008 + (L18)" , "1-008 + (L19)", "1-008 + (L20)", "1-008 + (M01)", "1-008 + (M02)", "1-008 + (M03)" , "1-008 + (M04)", "1-008 + (M05)", "1-008 + (M06)", "1-008 + (M07)", "1-008 + (M08)" , "1-008 + (M09)", "1-008 + (M10)", "1-008 + (M11)", "1-008 + (M12)", "1-008 + (M13)" , "1-008 + (M14)", "1-008 + (M15)", "1-008 + (M16)", "1-008 + (M17)", "1-008 + (M18)" , "1-008 + (M19)", "1-008 + (N01)", "1-008 + (N02)", "1-008 + (N03)", "1-008 + (N07)" , "1-008 + (N08)", "1-008 + (N12)", "1-008 + (O03)", "1-008 + (O05)", "1-008 + (P02)" , "1-008 + (P03)", "1-008 + (P04)", "1-008 + (P07)", "1-008 + (P10)", "1-008 + (Q02)" , "1-008 + (R01)", "1-008 + (R02)", "1-008 + (R03)", "1-008 + (R04)", "1-008 + (R05)" , "1-008 + (R06)", "1-008 + (R07)", "1-008 + (R08)", "1-008 + (R09)", "1-008 + (R10)" , "1-008 + (R11)", "1-008 + (R12)", "1-008 + (S01)", "1-008 + (S02)", "1-008 + (T01)" , "1-008 + (T02)", "1-008 + (T03)", "1-008 + (U01)", "1-008 + (U02)", "1-008 + (U03)" , "1-008 + (V01)", "1-008 + (V02)", "1-008 + (V03)", "1-008 + (V04)", "1-008 + (V05)" , "1-008 + (V06)", "1-008 + (W03)", "1-008 + (W04)", "1-008 + (W05)", "1-008 + (W09)" , "1-008 + (W10)", "1-008 + (X01)", "1-008 + (X02)", "1-008 + (X04)", "1-008 + (X05)" , "1-008 + (X08)", "1-008 + (X10)", "1-008 + (X11)", "1-008 + (Y01)", "1-008 + (Z01)" , "1-008 + (Z02)", "1-008 + (Z03)", "1-008 + (Z04)", "1-008 + (Z05)", "1-008 + (Z06)" , "1-008 + (Z07)", "1-008 + (Z08)", "1-008 + (Z09)", "1-008 + (Z10)", "1-008 + (Z12)" , "1-008 + (Z13)", "1-008 + (Z14)", "1-008 + (Z15)", "1-008 + (Z16)", "1-008 + (Z17)" , "1-008 + (Z18)", "1-008 + (Z19)", "1-008 + (Z20)", "1-008 + (Z21)", "1-009 + (A01)" , "1-009 + (A02)", "1-009 + (B01)", "1-009 + (B02)", "1-009 + (B03)", "1-009 + (B04)" , "1-009 + (B05)", "1-009 + (B06)", "1-009 + (B07)", "1-009 + (C01)", "1-009 + (C02)" , "1-009 + (C03)", "1-009 + (C04)", "1-009 + (C05)", "1-009 + (C06)", "1-009 + (C07)" , "1-009 + (C08)", "1-009 + (C09)", "1-009 + (C10)", "1-009 + (C11)", "1-009 + (C12)" , "1-009 + (C13)", "1-009 + (C14)", "1-009 + (C15)", "1-009 + (C16)", "1-009 + (C17)" , "1-009 + (C18)", "1-009 + (C19)", "1-009 + (C20)", "1-009 + (C21)", "1-009 + (C22)" , "1-009 + (C23)", "1-009 + (C24)", "1-009 + (C25)", "1-009 + (C26)", "1-009 + (C27)" , "1-009 + (C28)", "1-009 + (C29)", "1-009 + (C30)", "1-009 + (C31)", "1-009 + (C32)" , "1-009 + (C33)", "1-009 + (C34)", "1-009 + (C35)", "1-009 + (C36)", "1-009 + (C37)" , "1-009 + (C38)", "1-009 + (C39)", "1-009 + (C40)", "1-009 + (C41)", "1-009 + (C42)" , "1-009 + (C43)", "1-009 + (C44)", "1-009 + (C45)", "1-009 + (C46)", "1-009 + (D01)" , "1-009 + (D02)", "1-009 + (E01)", "1-009 + (E02)", "1-009 + (F01)", "1-009 + (F02)" , "1-009 + (G01)", "1-009 + (G02)", "1-0
09+ (H01), 1-009 + (H02), 1-009 + (H03), 1-009 + (H04), 1-009 + (H05), 1- 009+ (H06), 1-009 + (H07), 1-009 + (H08), 1-009 + (H09), 1-009 + (H10), 1- 009+ (H11), 1-009 + (H12), 1-009 + (H13), 1-009 + (H14), 1-009 + (H15), 1- 009+ (H16), 1-009 + (H17), 1-009 + (H18), 1-009 + (H19), 1-009 + (H20), 1- 009+ (H21), 1-009 + (H22), 1-009 + (H23), 1-009 + (H24), 1-009 + (H25), 1- 009+ (H26), 1-009 + (H27), 1-009 + (I01), 1-009 + (I02), 1-009 + (I03), 1- 009+ (I04), 1-009 + (I05), 1-009 + (I06), 1-009 + (I07), 1-009 + (J01), 1- 009+ (J02), 1-009 + (J03), 1-009 + (J04), 1-009 + (K01), 1-009 + (K02), 1- 009+ (K03), 1-009 + (K04), 1-009 + (K05), 1-009 + (L01), 1-009 + (L02), 1- 009+ (L03), 1-009 + (L04), 1-009 + (L05), 1-009 + (L06), 1-009 + (L07), 1- 0 09+ (L08), 1-009 + (L09), 1-009 + (L10), 1-009 + (L11), 1-009 + (L12), 1- 009+ (L13), 1-009 + (L14), 1-009 + (L15), 1-009 + (L16), 1-009 + (L17), 1- 009+ (L18), 1-009 + (L19), 1-009 + (L20), 1-009 + (M01), 1-009 + (M02), 1- 009+ (M03), 1-009 + (M04), 1-009 + (M05), 1-009 + (M06), 1-009 + (M07), 1- 009+ (M08), 1-009 + (M09), 1-009 + (M10), 1-009 + (M11), 1-009 + (M12), 1- 009+ (M13), 1-009 + (M14), 1-009 + (M15), 1-009 + (M16), 1-009 + (M17), 1- 009+ (M18), 1-009 + (M19), 1-009 + (N01), 1-009 + (N02), 1-009 + (N03), 1- 009+ (N07), 1-009 + (N08), 1-009 + (N12), 1-009 + (O03), 1-009 + (O05), 1- 009+ (P02), 1-009 + (P03), 1-009 + (P04), 1-009 + (P07), 1-009 + (P10), 1- 009+ (Q02), 1-009 + (R01), 1-009 + (R02), 1-009 + (R03), 1-009 + (R04), 1- 0 09+ (R05), 1-009 + (R06), 1-009 + (R07), 1-009 + (R08), 1-009 + (R09), 1- 009+ (R10), 1-009 + (R11), 1-009 + (R12), 1-009 + (S01), 1-009 + (S02), 1- 009+ (T01), 1-009 + (T02), 1-009 + (T03), 1-009 + (U01), 1-009 + (U02), 1- 009+ (U03), 1-009 + (V01), 1-009 + (V02), 1-009 + (V03), 1-009 + (V04), 1- 009+ (V05), 1-009 + (V06), 1-009 + (W03), 1-009 + (W04), 1-009 + (W05), 1- 009+ (W09), 1-009 + (W10), 1-009 + (X01), 1-009 + (X02), 1-009 + (X04), 1- 009+ (X05), 1-009 + (X08), 1-009 + (X10), 1-009 + (X11), 1-009 + (Y01), 1- 009+ (Z01), 1-009 + (Z02), 1-009 + (Z03), 1-009 + (Z04), 1-009 + (Z05), 1- 009+ (Z06), 1-009 + (Z07), 1-009 + (Z08), 1-009 + (Z09), 1-009 + (Z10), 1- 009+ (Z12), 1-009 + (Z13), 1-009 + (Z14), 1-009 + (Z15), 1-009 + (Z16), 1- 0 09+ (Z17), 1-009 + (Z18), 1-009 + (Z19), 1-009 + (Z20), 1-009 + (Z21), 2- 001+ (A01), 2-001 + (A02), 2-001 + (B01), 2-001 + (B02), 2-001 + (B03), 2- 001+ (B04), 2-001 + (B05), 2-001 + (B06), 2-001 + (B07), 2-001 + (C01), 2- 001+ (C02), 2-001 + (C03), 2-001 + (C04), 2-001 + (C05), 2-001 + (C06), 2- 001+ (C07), 2-001 + (C08), 2-001 + (C09), 2-001 + (C10), 2-001 + (C11), 2- 001+ (C12), 2-001 + (C13), 2-001 + (C14), 2-001 + (C15), 2-001 + (C16), 2- 001+ (C17), 2-001 + (C18), 2-001 + (C19), 2-001 + (C20), 2-001 + (C21), 2- 001+ (C22), 2-001 + (C23), 2-001 + (C24), 2-001 + (C25), 2-001 + (C26), 2- 001+ (C27), 2-001 + (C28), 2-001 + (C29), 2-001 + (C30), 2-001 + (C31), 2- 001+ (C32), 2-001 + (C33), 2-001 + (C34), 2-001 + (C35), 2-001 + (C36), 2- 0 01+ (C37), 2-001 + (C38), 2-001 + (C39), 2-001 + (C40), 2-001 + (C41), 2- 001+ (C42), 2-001 + (C43), 2-001 + (C44), 2-001 + (C45), 2-001 + (C46), 2- 001+ (D01), 2-001 + (D02), 2-001 + (E01), 2-001 + (E02), 2-001 + (F01), 2- 001+ (F02), 2-001 + (G01), 2-001 + (G02), 2-001 + (H01), 2-001 + (H02), 2- 001+ (H03), 2-001 + (H04), 2-001 + (H05), 2-001 + (H06), 2-001 + (H07), 2- 001+ (H08), 2-001 + (H09), 2-001 + (H10), 2-001 + (H11), 2-001 + (H12), 2- 001+ (H13), 2-001 + (H14), 2-001 + (H15), 2-001 + (H16), 2-001 + (H17), 2- 001+ (H18), 2-001 + (H19), 2-001 + (H20), 2-001 + (H21), 2-001 + (H22), 2- 001+ (H23), 2-001 + (H24), 2-001 + (H25), 2-001 + (H26), 2-001 + (H27), 2- 001+ (I01), 2-001 + (I02), 2-001 + (I03), 2-001 + (I04), 2-001 + (I05), 2- 0 01+ (I06), 2-001 + (I07), 2-001 + (J01), 2-001 + (J02), 2-001 + (J03), 2- 001+ (J04), 2-001 + (K01), 2-001 + (K02), 2-001 + (K03), 2-001 + (K04), 2- 001+ (K05), 2-001 + (L01), 2-001 + (L02), 2-001 + (L03), 2-001 + (L04), 2- 001+ (L05), 2-001 + (L06), 2-001 + (L07), 2-001 + (L08), 2-001 + (L09), 2- 001+ (L10), 2-001 + (L11), 2-001 + (L12), 2-001 + (L13), 2-001 + (L14), 2- 001+ (L15), 2-001 + (L16), 2-001 + (L17), 2-001 + (L18), 2-001 + (L19), 2- 001+ (L20), 2-001 + (M01), 2-001 + (M02), 2-001 + (M03), 2-001 + (M04), 2- 001+ (M05), 2-001 + (M06), 2-001 + (M07), 2-001 + (M08), 2-001 + (M09), 2- 001+ (M10), 2-001 + (M11), 2-001 + (M12), 2-001 + (M13), 2-001 + (M14), 2- 001+ (M15), 2-001 + (M16), 2-001 + (M17), 2-001 + (M18), 2-001 + (M19), 2- 0 01+ (N01), 2-001 + (N02), 2-001 + (N03), 2-001 + (N07), 2-001 + (N08), 2- 001+ (N12), 2-001 + (O03), 2-001 + (O05), 2-001 + (P02), 2-001 + (P03), 2- 001+ (P04), 2-001 + (P07), 2-001 + (P10), 2-001 + (Q02), 2-001 + (R01), 2- 001+ (R02), 2-001 + (R03), 2-001 + (R04), 2-001 + (R05), 2-001 + (R06), 2- 001+ (R07), 2-001 + (R08), 2-001 + (R09), 2-001 + (R10), 2-001 + (R11), 2- 001+ (R12), 2-001 + (S01), 2-001 + (S02), 2-001 + (T01), 2-001 + (T02), 2- 001+ (T03), 2-001 + (U01), 2-001 + (U02), 2-001 + (U03), 2-001 + (V01), 2- 001+ (V02), 2-001 + (V03), 2-001 + (V04), 2-001 + (V05), 2-001 + (V06), 2- 001+ (W03), 2-001 + (W04), 2-001 + (W05), 2-001 + (W09), 2-001 + (W10), 2- 001+ (X01), 2-001 + (X02), 2-001 + (X04), 2-001 + (X05), 2-001 + (X08), 2- 0 01+ (X10), 2-001 + (X11), 2-001 + (Y01), 2-001 + (Z01), 2-001 + (Z02), 2- 001+ (Z03), 2-001 + (Z04), 2-001 + (Z05), 2-001 + (Z06), 2-001 + (Z07), 2- 001+ (Z08), 2-001 + (Z09), 2-001 + (Z10), 2-001 + (Z12), 2-001 + (Z13), 2- 001+ (Z14), 2-001 + (Z15), 2-001 + (Z16), 2-001 + (Z17), 2-001 + (Z18), 2- 001+ (Z19), 2-001 + (Z20), 2-001 + (Z21), 3-001 + (A01), 3-001 + (A02), 3- 001+ (B01), 3-001 + (B02), 3-001 + (B03), 3-001 + (B04), 3-001 + (B05), 3- 001+ (B06), 3-001 + (B07), 3-001 + (C01), 3-001 + (C02), 3-001 + (C03), 3- 001+ (C04), 3-001 + (C05), 3-001 + (C06), 3-001 + (C07), 3-001 + (C08), 3- 001+ (C09), 3-001 + (C10), 3-001 + (C11), 3-001 + (C12), 3-001 + (C13), 3- 001+ (C14), 3-001 + (C15), 3-001 + (C16), 3-001 + (C17), 3-001 + (C18), 3- 0 01+ (C19), 3-001 + (C20), 3-001 + (C21), 3-001 + (C22), 3-001 + (C23), 3- 001+ (C24), 3-001 + (C25), 3-001 + (C26), 3-001 + (C27), 3-001 + (C28), 3- 001+ (C29), 3-001 + (C30), 3-001 + (C31), 3-001 + (C32), 3-001 + (C33), 3- 001+ (C34), 3-001 + (C35), 3-001 + (C36), 3-001 + (C37), 3-001 + (C38), 3- 001+ (C39), 3-001 + (C40), 3-001 + (C41), 3-001 + (C42), 3-001 + (C43), 3- 001+ (C44), 3-001 + (C45), 3-001 + (C46), 3-001 + (D01), 3-001 + (D02), 3- 001+ (E01), 3-001 + (E02), 3-001 + (F01), 3-001 + (F02), 3-001 + (G01), 3- 001+ (G02), 3-001 + (H01), 3-001 + (H02), 3-001 + (H03), 3-001 + (H04), 3- 001+ (H05), 3-001 + (H06), 3-001 + (H07), 3-001 + (H08), 3-001 + (H09), 3- 001+ (H10), 3-001 + (H11), 3-001 + (H12), 3-001 + (H13), 3-001 + (H14), 3- 0 01+ (H15), 3-001 + (H16), 3-001 + (H17), 3-001 + (H18), 3-001 + (H19), 3- 001+ (H20), 3-001 + (H21), 3-001 + (H22), 3-001 + (H23), 3-001 + (H24), 3- 001+ (H25), 3-001 + (H26), 3-001 + (H27), 3-001 + (I01), 3-001 + (I02), 3- 001+ (I03), 3-001 + (I04), 3-001 + (I05), 3-001 + (I06), 3-001 + (I07), 3- 001+ (J01), 3-001 + (J02), 3-001 + (J03), 3-001 + (J04), 3-001 + (K01), 3- 001+ (K02), 3-001 + (K03), 3-001 + (K04), 3-001 + (K05), 3-001 + (L01), 3- 001+ (L02), 3-001 + (L03), 3-001 + (L04), 3-001 + (L05), 3-001 + (L06), 3- 001+ (L07), 3-001 + (L08), 3-001 + (L09), 3-001 + (L10), 3-001 + (L11), 3- 001+ (L12), 3-001 + (L13), 3-001 + (L14), 3-001 + (L15), 3-001 + (L16), 3- 001+ (L17), 3-001 + (L18), 3-001 + (L19), 3-001 + (L20), 3-001 + (M01), 3- 0 01+ (M02), 3-001 + (M03), 3-001 + (M04), 3-001 + (M05), 3-001 + (M06), 3- 001+ (M07), 3-001 + (M08), 3-001 + (M09), 3-001 + (M10), 3-001 + (M11), 3- 001+ (M12), 3-001 + (M13), 3-001 + (M14), 3-001 + (M15), 3-001 + (M16), 3- 001+ (M17), 3-001 + (M18), 3-001 + (M19), 3-001 + (N01), 3-001 + (N02), 3- 001+ (N03), 3-001 + (N07), 3-001 + (N08), 3-001 + (N12), 3-001 + (O03), 3- 001+ (O05), 3-001 + (P02), 3-001 + (P03), 3-001 + (P04), 3-001 + (P07), 3- 001+ (P10), 3-001 + (Q02), 3-001 + (R01), 3-001 + (R02), 3-001 + (R03), 3- 001+ (R04), 3-001 + (R05), 3-001 + (R06), 3-001 + (R07), 3-001 + (R08), 3- 001+ (R09), 3-001 + (R10), 3-001 + (R11), 3-001 + (R12), 3-001 + (S01), 3- 001+ (S02), 3-001 + (T01), 3-001 + (T02), 3-001 + (T03), 3-001 + (U01), 3- 0 01+ (U02), 3-001 + (U03), 3-001 + (V01), 3-001 + (V02), 3-001 + (V03), 3- 001+ (V04), 3-001 + (V05), 3-001 + (V06), 3-001 + (W03), 3-001 + (W04), 3- 001+ (W05), 3-001 + (W09), 3-001 + (W10), 3-001 + (X01), 3-001 + (X02), 3- 001+ (X04), 3-001 + (X05), 3-001 + (X08), 3-001 + (X10), 3-001 + (X11), 3- 001+ (Y01), 3-001 + (Z01), 3-001 + (Z02), 3-001 + (Z03), 3-001 + (Z04), 3- 001+ (Z05), 3-001 + (Z06), 3-001 + (Z07), 3-001 + (Z08), 3-001 + (Z09), 3- 001+ (Z10), 3-001 + (Z12), 3-001 + (Z13), 3-001 + (Z14), 3-001 + (Z15), 3- 001+ (Z16), 3-001 + (Z17), 3-001 + (Z18), 3-001 + (Z19), 3-001 + (Z20), 3- 001+ (Z21) ".

  The characteristics of the composition of the present invention and the method of the present invention are as follows. Firstly, the insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effects are evident as compared with the case where each drug is applied alone. In addition to being enhanced, it provides immediate insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effects. Second, the existing insecticidal, acaricidal, nematicidal, molluscicidal, broad insecticidal, acaricidal, nematicidal, molluscicidal, germicidal or bactericidal spectrum not seen in bactericides or bactericides It is that aftereffect is induced. Thirdly, compared to the case where each drug is used alone, the amount of dropped drug can be reduced.

  That is, the composition of the present invention and the method of the present invention exhibit synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effects. This synergistic insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect is predicted from the insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal effect of each single agent. It can be said that the usefulness of the composition of the present invention and the method of the present invention is that it can exert a more reliable control effect than various compounds alone against various pests.

The active compound I as one or two first active ingredients and the active compound II as one or more second active ingredients in the present invention are applied by various application methods as follows. Can do.
1. Simultaneous application, ie
a) Mixed application (ie as a mixture, eg ready-to-use formulations or as a tank mix)
b) Individual application (ie application in separate tanks), or
2. The continuous individual application, in this case the sequence, generally does not have any influence on the results of the control method.

  Therefore, a method for controlling pests, mites, nematodes, molluscs, pests and bacteria can be achieved by applying active compound I and active compound II separately or together, or by active compound I. And by application or dusting of the seed, plant or soil with the active compound II mixture before or after sowing or before or after plant emergence.

  A suitable mixing ratio (weight ratio) of the active compound I which is the first active ingredient and the active compound II which is the second active ingredient in the composition of the present invention and the method of the present invention is 100: It can be used in the range of 1 to 1: 100, preferably 20: 1 to 1:20, particularly 10: 1 to 1:10.

  The preferred treatment amount of the active ingredient compound in the composition of the present invention and the method of the present invention depends on the type of the target pest to be controlled, etc., but usually the active compound I as the first active ingredient is 0.1 to 1000 gai. / Ha, the active compound II as the second active ingredient is 0.1 to 1000 gai / ha, preferably the former is 1 to 300 gai / ha and the latter is 1 to 300 gai / ha.

  The composition of the present invention is a so-called agricultural pest that harms agricultural and horticultural crops and trees, agricultural diseases, so-called livestock pests parasitic on livestock poultry, so-called sanitary pests that adversely affect the human living environment such as houses, and the like It can be applied to mites, nematodes, and molluscs that occur and harm the scene. Specific examples of pests, mites, nematodes, molluscs, and diseases that can be controlled using the composition of the present invention include the following, but are not limited thereto.

The pests include the chestnut bees Chestnut gall wasp (Dryocosmus kuriphilus), the Argentine ant Argentine ant (Linepithema humile), the Guntai ant Army ant (Eciton burchelli, E. schmitti), the black ant Japanese carpenter ant (Camponotus japonicus), or oh ihime , Bulldog ant (Myrmecia spp.), Fire Ant (Solenopsis spp.), Asian giant hornet (Vespa mandarina), Japanese yellow hornet (Vespa simillima), Large roseana fly (Arge pag) ), Pine bee European pine sawfly (Neodiprion sertifer), chestnut bee Chestnut sawfly (Apethymus kuri), red bee Cabbage sawfly (Athalia infumata), beech turnip sawfly (Athalia rosae) and other insects (Hyoptera)
Pear leaf miner (Bucculatrix pyrivorella), Tea leafroller (Caloptilia theivora), Golden leaf moth Apple leafminer (Phyllonorycter ringoniella), Citrus leafminer (Phyllocnistis citrella), Impressive worms Persimmon fruit moth (Stathmopoda masinissa), Peach fruit moth (Carposina sasakii), Allium leafminer (Acrolepiopsis sapporensis), Yam leafminer (Acrolepiopsis suzukiella), Peach fruit moth (Pel fruit) ), Diamondback moth (Plutella xylostella), red stem borer (Chilo suppressalis), Shibatatsuga Bluegrass webworm (Parapediasia teterrella) Cabbage webworm (Hellula undalis), Rice leaf roller (Cnaphalocrocis medinalis), Yellow moth moth (Conogethes punctiferalis), Cotton moth (Diaphania indica), Mulberry pyras (Mulberry pyras) Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Azuki bean borer (Ostrinia scapulalis), sorghum moth Lesser corn stalk borer (Elasmopalpus lignosellus), ella borer L Tree borer Peach tree borer (Synanthedon exitiosa), Cosca Shiba Cherry tree borer (Synanthedon hector), Kubiakasukashiba (Toleria romanovi), Iraga Oriental moth (Monema flavescens), Auraigaga (Parasa consocia), Hiroheliaiairaga lepida), Parasa siniea, Takenohosokuroba (Artona martini), Ringworm (Illiberis pruni), Umeska cycloba (Illiberis rotundata), Carpenter moth (Cossus insularis), Codling moth (Cyling monkey) Fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita molesta), Bean pod borer (Leguminivora glycinivorella), Bean podworm (Matsumuraeses phaseoli), Grapeberry moss (Grape berryite moth, Endopiza) Smaller tea tortrix (Adoxophyes honmai), Apple coconut oyster Summer fruit tortrix (Adoxophyes orana fasciata), Apple peach oyster Asiatic leafroller (Archips breviplicanus), Midareka kumamaki Apple tortrix (Archips fuscocupreanus) Oriental tea tortrix (Homona magnanima), Tobihamaki Dark fruit-tree tortrix (Pandemis heparana), Matsukareha Pine moth (Dendrolimus spectabilis), Tsunakareha Jananese hemlock caterpillar (Dendrolimus superans), Takekareha Japanese bamboo thrix hare Euthrix potatoria, Oriental lappet (Gastropacha orientalis), Kunugia undans, Kunugia yamadai, tomato hornworm Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm Tofacco mothworm cunea), Mulberry tiger moth (Lemyra imparilis), white flies (Eilema fuscodorsalis), black buckwheat (Eilema laevis), white moths udoconspersa), Swan moth (Sphrageidus similis), Gypsy moth (Lymantria dispar), White-spotted tussock moth (Orgyia thyellina), Rice green caterpillar (Naranga aenescens), Naranga aenescens leaf worm (Aedia leucomelas), mushrooms Cabbage armyworm (Mamestra brassicae), mushrooms Oriental armyworm (Pseudaletia separata), swordfish Lawn grass cutworm (Spodoptera depravata), southern army worms Southern armyworm (ex pods), pods Fall army worm Fall armyworm (Spodoptera frugiperda), cotton leaf worm Cotton leafworm (Spodoptera littoralis), common cutworm (Spodoptera litura), giant bollworm (Helicoverpa armigera), tobacco moth Orienta l tobacco budworm (Helicoverpa assulta), tobacco bad worm Tobacco budworm (Heliothis virescens), American tobacco moth Corn earworm (Helicoverpa zea), Japanese red moth Black cutworm (Agrotis ipsilon), Kaburaya moth Turnip moth (Agrotis segetum) ), Honey beetle Threespotted plusia (Ctenoplusia agnata), soy bean looper Soybean looper (Pseudoplusia includens), nettle cabbage Cabbage looper (Trichoplusia ni), mugwort Japanese giant looper (Ascotis selenaria), brass white white butterfly P , Lepidoptera (Lepidoptera), Lepidoptera such as Cabbage white butterfly (Pieris rapae crucivora), Strawberry swift (Parnara guttata), Cotton leafworm (Alabama argillacea), Sugarcane borer (Diatraea sacharalis) Insect,
The fruit fly Melon fly (Bactrocera cucurbitae), the fruit fly Oriental fruit fly (Bactrocera dorsalis), the Queensland fruit fly Queensland fruit fly (Bactrocera tryoni), the fruit fly Japanese orange fly (Bactrocera tsuneonis), the Mediterranean fruit fly Mediterraneitis fruit fly (Anastrepha ludens), ring-fly fly Apple maggot (Rhagoletis pomonella), rice leaf fly Rice leaf miner (Agromyza oryzae), leaf leaf flyer Pea leaf miner (Chromatomyia horticola), oilseed leaf fly Cabbage leafminer (Liriomyza brassicae), Liriomyza brassicae ), Green leaf fly Stone leek leafminer (Liriomyza chinensis), green leaf fly Pea leafminer (Liriomyza huidobrensis), tomato leaf fly Tomato leafminer (Liriomyza sativae), bean leaf fly Serpentine leafminer (Liriom yza trifolii), Japanese fruit fly (Drosophila suzukii), Small leaf rice leaf miner (Hydrellia griseola), Tsetse fly (Glossina morsitans, G. palpalis), White fly, Forest fly (Hippobca) Melophagus ovinus), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), sugar beet fly, Beet leaf miner (Pegomya cunicularia), Lesser house fly (Fannia canicularis), Sheep head fly (Hritae flyfly) ), Sweet fly (Morellia simplex), Face fly (Musca autumnalis), Housefly (Musca domestica), Australian bush fly (Musca vetustissima), Horn fly (Haematobia irritans), Stable fly (Stable fly) Stomoxys calci trans, Calliphora lata, Bottle fly (Calliphora vicina), Old World screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya, Chrysomya America) New World screw-worm fly (Cochliomyia hominivorax), Black blow fly (Phormia regina), Northern flyfly (Protophormia terraenovae), sheep fly Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris) Common green bottle fly (Lucilia sericata), Bot flies (Cuterebra spp.), Human botfly (Dermatobia hominis), Horse-nosed bot fly (Gasterophilus haemorrhoidalis), Horse-fly Horis bottest t fly (Gasterophilus nasalis), Bullflies Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Sheep nasal bot fly (Oestrus ovis), Fresh fly Flesh fly (Sarcophaga carnaria), Sentinic fly F ), Splayed deerfly (Chrysops caecutiens), Mekurabu Deer fly (Chrysops suavis), Common horse fly (Haematopota pluvialis), Greenhead horsefly (Greenhead horse fly (Tabanus nigrovittatus), Bovine horsefly (Tabanus trigonus) ), Soybean soybean pod gall midge (Asphondylia yushimai), Hessian fly Hessian fly (Mayetiola destructor), brown wheat blossom midge (Sitodiplosis mosellana), chick nuka Biting midge (Culicoides arakawae), L nipponens is), Black-headed Blackfish (Prosimulium yezoensis), Black fly (Simulium ochraceum), African Malaria mosquito (Anopheles gambiae), Red-backed Shrimp (Anopheles hyrcanus sinesis), Anophelestosi aegypti), Asian tiger mosquito (Aedes albopictus), House mosquito (Culex pipiens molestus), House mosquito (Culex pipiens pallens), Culex tritaeniorhynchus, fly P butterfly (S) Diptera insects such as Telmatoscopus albipunctatus)
Tobacco beetle (Lasioderma serricorne), Common bean weevil (Acanthoscelides obtectus), Adzuki bean beetle (Callosobruchus chinensis), Grape borer (Xylotrechus pyrrhoder beetle) White-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine sawyer (Monochamus alternatus), Yellow-spotted longicorn beetle (Psacothea hilaris), Colorado beetle Colorado beetle beetle (Phaedon cochleariae), rice leaf beetle Rice leaf beetle (Oulema oryzae), spotted beetle Reaf beetle (Demotina fasciculata), cucumber leaf beetle (Aulacophora femoralis) Beet flea beetle (Chaetocnema concinna), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm Western corn rootworm (Diabrotica virgifera), Triped P flea beetle striolata), Solanum flea beetle (Psylliodes angusticollis), green beetle Mexican been beetle (Epilachna varivestis), large twenty-eight-spotted ladybird (Epilachna vigintioctomawata bird), (Epilachna vigintioctopunctata), Epuraea domina, Pollen beetle (Meligethes aeneus), Peach curculio (Rhynchites heros), Sweetpotato weevil (Cylas formicarius), potato weevil West Indian sweet potato weevil (Euscepes postfasciatus), cotton weevil Boll weevil (Anthonomus grandis), white-flying beetle White-fringed beetle (Graphognatus leucoloma), horned beetle weevil Octopus weevil Alfalfa weevil (Hypera postica), Granary weevil (Sitophilus granarius), weevil Maize weevil (Sitophilus zeamais), Shibao weevil Hunting billbug (Sphenophorus venatus vestitus), weevil weevil (Lissohoptrus oryzophilus), yellow mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum), sweet potato wireworm (Melanotus fortnumi), citrus fruit Tsuruga Sugarcane wireworm (Melanotus tamsuyensis), core red clover Citrus flower chafer (Gametis jucunda), Nagachakogane, Yellowish elongate chafer (Heptophylla picea), Douganebuibu Cupreous chafer (Anomala cuprea), Japanese beetle ), Coleoptera insects such as Rove beetle (Paederus fuscipes),
Asian citrus psyllid (Diaphorina citri), pear sucker Pear sucker (Psylla pyrisuga), whitefly Camellia spiny whitefly (Aleurocanthus camelliae), orange spiny whitefly (Aleurocanthus spiniferus), white leaffly (Aleurocanthus spiniferus) Whitefly Sweetpotato whitefly (Bemisia tabaci), Citrus whitefly (Dialeurodes citri), Greenhouse whitefly (Trialeurodes vaporariorum), Pea aphid (Acyrthosiphon pisum), Bean accura beetle Aphid aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Green apple aphid (Aphis pomi), Spiraea aphid (Spiraea aphid) Aphis spiraecola), Foxglove aphid (Aulacorthum solani), Leaf curl plum aphid (Brachycaudus helichrysi), Japanese aphid Cabbage aphid (Brevicoryne brassicae), Walnut aphid Wola Russian wheat aphid (Diuraphis noxia), plantain beetle Rosy apple aphid (Dysaphis plantaginea), peach beetle Mealy plum aphid (Hyalopterus pruni), black pea aphid Turnip aphid (Lipaphis erysimi), tulip beetle aphid Margin door aphid (Monellia caryella), peach aphid Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Nephia Onion aphid (N eotoxoptera formosana), wheat cherry-oat aphid (Rhopalosiphum padi), rice aphid Rice root aphid (Rhopalosiphum rufiabdominalis), wheat leaf aphid (Sitobion akebiae) phi avenae), green bug (Schizaphis graminum), black citrus aphid (Toxoptera aurantii), citrus aphid Brown citrus aphid (Toxoptera citricida), apple weevil Wooly apple aphid (Eriosoma lanigerum), rape aphid Viteus vitifolii), hornet beetle Indian wax scale (Ceroplastes ceriferus), ruby weevil Red wax scale (Ceroplastes rubens), citrus scale insect (Coccus pseudomagnoliarum), red beetle California red scale (Aonidiella aurantii), pear Scale scale San jose scale (Comstockaspis perniciosa), scale scale tea scale (Teori scale) Peony scale (Pseudaonidia paeoniae), scale beetle scale Mulberry scale (Pseudaulacaspis pentagona), white scale scale Pula scale Citrus snow scale (Unaspis citri), Euonymus scale (Unaspis euonymi), Agarhead scale (Unaspis yanonensis), Giant margarodid scale (Drosicha corottenta scale) purchasi), worm beetle Cotton mealy bug (Phenacoccus solani), citrus mealybug (Citrus mealybug (Planococcus citri)), Japanese mealybug (Planococcus kuraunhiae), stag beetle Comstock me alybug (Pseudococcus comstocki), grape meal bug (Pseudococcus maritimus), brown brown planthopper (Laodelphax striatella), brown rice planthopper (Nilaparvata lugens), white-backedella planta (Gifera) Leafhopper (Epiacanthus stramineus), Indian cotton leafhopper (Amrasca devastans), Greenbird leafhopper (Balclutha saltuella), Aster leafhopper (Macrosteles fascifrons), Amber leafhopper (Macrosteles fascifrons), Greenleaf leafhopper (Macrosteles striifrons) leafhopper (Nephotettix cincticeps), Grape Leafhopper (Arboridia apicalis), Potato Leafhopper (Empoasca fabae), Emporasca nipponica, Chaomi Green leafhopper (Empoasca onukii), Bean's smaller green leafhopper (Empoasca sakaii), Sleek bug (Dolycoris baccarum), Japanese turtle Cabbage bug (Eurydema rugosa), Spined whitespot ), White-spotted stink bug (Eysarcoris ventralis), Blue-headed stink bug (Glaucias subpunctatus), Brown marmorated stink bug (Halyomorpha haly) Nezara antennata, Southern green stink bug (Nezara viridula), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Brown-winged cross bug (Brown-winged cross bug) Japanese black rice bug (Scotinophora lurida), Bean bug (Riptortus clavatus), Spider helicopter Rice bug (Leptocorisa chinensis), Japanese stink bug Rice stink bug (Cletus punctiger), Southern bug shrimp bug (Paradasynus spinosus), Red-backed Helicopteran Rhopalid bug (Rhopalus maculatus), American Red-footed Beetle True chinch bug (Blissus leucopterus), Japanese Red-headed Bug, Oriental chinch bug (Cavelerius saccharivorus) Red cotton bug (Dysdercus cingulatus), Venezuelan sand turtle Blood-sucking bug (Rhodnius prolixus), Mexican sand turtle Kissing bug (Triatoma dimidiata), Brazilian sand turtle Kissing bug (Triatoma infestans), Green stink bug ), Blown Stink bag brown stink bug (Euschistus servus), Southern green stink bag (Nezara viridula), Tarnished plant bug (Lygus lineolaris), Stink bag (Dichelops furcatus), Sugarcans pitle bag sugarcane spittlebug (Mahanarva fimbriolata), azalea lace bug (Stephanitis pyrioides), bed bug Bed bug (Cimex lectularius), bluefin turtle Pale greenplant bug (Apolygus spinolae), western tarnished plant bug (Lygus hesperus) Tarnished plant bug (Lygus lineolaris), Nagasugikasikameka Rice stink bug (Stenodema sibiricum), Akasujikasikameka Sorghum plant bug (Stenotus rubrovittatus), Rice-butterfly turtle Rice leaf bug (Trigonotylus caelestlium mosquito) Hemiptera insects such as and fleahopper (Halticus insularis), Cotton fleahopper (Pseudatomoscelis seriatus), Flower thrips (Frankliniella intonsa), Green thrips Yellow tea thrips (Scirtothrips dorsalis), Southern thrips Melon thrips (Thrips palmi), Black thrips Onion thrips (Thrips tabaci), Japanese gall-forming thrips (optonicthrips) ,
Desert locust (Schistocerca gregaria), Australian platypus locust Australian plague locust (Chortoicetes terminifera), locust grasshopper Migratory locust (Locusta migratoria), red-footed locust Lesser paddy grasshopper (Oxya japonica), red-leafed grasshopper (Oxya japonica) (Teleogryllus emma), Kela Oriental mole cricket (Gryllotalpa orientalis), etc.
German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta jaligonica), Japanese cockroach (Periplaneta japonica), Daiikokuus tomatoes (America) Termite Western dry-wood termite (Incisitermes minor), Common termite Formosan subterranean termite (Coptotermes formosanus), Japanese termite termite Japanese subterranean termite (Reticulitermes speratus), Thai termite Black-winged subterranean termite (Odontotermes formosanus) ,
Rootfeeding springtail (Onychiurus folsomi), Siberian white beetle (Onychiurus sibiricus), Garden springtail (Bourletiella hortensis), etc.
Isopoda crustaceans such as Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber),
Tobism cadets, Chinese red-headed centipede (Scolopendra subspinipes mutilans), Acolm cadets (Scolopendra japonica), Scolopendra multidens, etc.
Lithobiomorpha polypods, such as Bothropolys asperatus
Scutigeromorpha polypods Brown-legged grain mite (Aleuroglyphus ovatus), spinach mite (Tyrophagus similis), Robin mite Bulb mite (Rrobizly) Mites,
Wheat curl mite (Aceria tulipae), Pear rust mite (Eriophyes chibaensis), Peach bud mite (Eriophyes insidiosus), Pearleaf blister mite Pearleaf blister mite (Eriophyes pyri), Chaonaga rust mite Tea rust mite (Acaphylla theavagrans), tomato rustset mite (Aculops lycopersici), citrus red mite Pink citrus rust mite (Aculops pelekassi), apple rust mite (Aculus schlechtendali), citrus rustloite mite (Polyphagotarsonemus latus), Cyclamen mite Cyclamen mite (Phytonemus pallidus), Dwarf dust mite Tarsonemid mite (Tarsonemus bilobatus), Rice spider mite (Oligonychus shinkajii), Citrus mite Citrus red mite (Panonychus mite) , Apple spider mite European red mite (Panonychus ulmi), Kanzawa spider mite Kanzawa spider mite (Tetranychus kanzawai), spider mite Two-spotted spider mite (Tetranychus urticae), spider mite (Penthaleus erythrocephalus), wheat spider mite (Penthaleus erythrocephalus) ), Stag mite (Leptotrombidium pallida), tsutsugamushi mite (Leptotrombidium scutellare), mite subspecies, such as the tick mite (Proteum)
Pancreas (Architaenioglossa) gastropod, such as Apple snail (Pomacea canaliculata)
African Mystic Giant African snail (Achatina fulica), Black-tailed slug Terrestrial slug (Limax marginatus), Slug (Meghimatium bilineatum), Korean round snail (Acusta despecta sieboldiana), Miss my mai Land snio (Euhadra mai) Eyes (Stylommatophora) gastropods,
Rice white nematode (Aphelenchoides besseyi), Pine wood nematode (Bursaphelenchus xylophilus) nematode (Aphelenchida) nematode,
Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode Cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Seterbean cyst nematode (Heterodera glycines)), Alenaria root nematode (Peanut root-Menotnene nede) -knot nematode (Meloidogyne hapla), Southern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Southern root-kion nematode Coffee root-lesion nematode (Pratylus nechude) Root-lesion nematode (Pratylenchus loosi), Cobb's root-lesion nematode (Pratylenchus penetrans), Walnut root-lesion nematode (Pratylenchus vulnus), etc. lenchida) nematode,
Pests in the field of agriculture, forestry and horticulture that can be controlled using the compounds of the present invention and so-called sanitary pests that adversely affect human living environments such as houses, and ticks and nematodes that occur in similar situations The molluscs and molluscs are not limited to these.

On the other hand, as a specific disease, for example,
Diseases of konjac: dry rot Dry rot (Fusarium oxysporum, F. solani f. Sp. Radicicola), white silkworm Stem rot (Athelia rolfsii), root rot Root rot (Pythium aristosporum), leaf blight Bacterial leaf blight ( Acidovorax konjaci), rot soft rot (Erwinia carotovora subsp. Carotovora).

  Diseases of taro: Leaf mold (Cladosporium colocasiae), dry rot Dry rot (Fusarium oxysporum f. Sp. Colocasiae), black rot Black rot (Ceratocystis sp.), Plague Phytophthora blight (Phytophthora colocasiae), root rot Disease (Pythium aristosporum, P. myriotylum), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Diseases of leek crops: Yellow spot Leaf spot (Heterosporium allii), Black spot disease Alternaria leaf spot (Alternaria porri), Leaf blight Leaf spot (Pleospora herbarum, Stemphylium botryosum, S. vesicarium), Pink root rot (Pyrenochaeta terrestris, Pyrenochaeta sp.), Leaf blight leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), red mold gray mold (Botrytis cinerea), onion gray rot Onion gray mold neck rot (Botrytis allii), small sclerotial rot (Botrytis squamosa), small sclerotia disease Leaf blight (Ciborinia allii), dry rot dry rot (Fusarium oxysporum), dry rot fungus Fusarium basal rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), onion fusarium basal rot (Fusarium oxysporum f. cepae), rust Rust (Puccinia allii), smut Smut (Urocystis cepulae), black rot Mycorrhizal disease Allium white rot (Sclerotium cepivorum), white Silk blight Southern blight (Athelia rolfsii), seedling blight Damping-off (Rhizoctonia solani, Pythium sp.), Downy mildew (Peronospora destructor), plague Phytophthora blight (Phytophthora nicotianae), white plague Leaf blight (Phytophthora) ), Onion rot disease Onion soft rot (Burkholderia cepacia), spring rot Bacterial rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, Erwinia sp.), Leek strain rot fungus Bacterial basal bulb rot (Pseudomonas sp.), Soft rot Disease Bacterial soft rot (Pectobacterium carotovorum).

  Diseases of asparagus: Brown spot disease Leaf spot (Cercospora asparagi), Spot disease Stemphylium leaf spot (Stemphylium botryosum), Stem blight Stem blight (Phomopsis asparagi).

  Potato disease: Brown rot (Fusarium oxysporum, F. solani f. Sp. Pisi, f. Sp. Radicicola), anthracnose Anthracnose (Glomerella cingulata), leaf astringency Leaf spot (Pseudophloeosporella dioscoreae).

  Diseases of rice: Stem rot (Helminthosporium sigmoideum var. Irregulare), Brown spot (Cochliobolus miyabeanus), Seedling blight (Phoma sp., Trichoderma viride, Fusarium solani, Gibberella avenacea, Mucor) fragilis, Rhizopus arrhizus, R. chinensis, R. oryzae, Pythium arrhenomanes, P. graminicola, P. irregulare, P. spinosum, P. sylvaticum), rice smoldering disease False smut (Villosiclava virens), “Bakaane” dise (Gibberella fujikuroi), blast disease Blast (Magnaporthe grisea), staphylococcal nuclear disease Stem rot (Magnaporthe salvinii), blight disease, Sheath blight (Thanatephorus cucumeris), Bacterial grain rot (Burkholderia gladioli, B. glumae), Bacterial seedling blight (Burkholderia plantarii), brown stripe disease Bacterial brown stripe (Acidovorax avenae subsp. Avenae), white leaf blight Bacterial leaf blight (Xanthomonas oryzae pv. Oryzae), inner bud browning disease Bacterial palea browning (Pantoe a ananatis).

  Diseases of wheat: Speckled leaf blotch (Mycosphaerella graminicola), glaze blotch (Phaeosphaeria nodorum), spot blotch (Cochliobolus sativus), barley leaf spot (Pyrenophora graminea), barley net blotch Disease Barley net blotch (Pyrenophora teres), Barley powdery mildew (Blumeria graminis f. Sp. Hordei), Wheat powdery mildew (Blumeria graminis f. Sp. Tritici), Rye powdery mildew (Blumeria graminis f. Sp. Secalis), eye spot disease Eyespot (Tapesia acuformis, T. yallundae), snow rot large-sized mycobacterial disease Sclerotinia snow blight (Sclerotinia borealis), ergot disease Ergot (Claviceps purpurea), Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae), blight Take-all (Gaeumannomyces graminis), red snow rot Snow mold (Monographella nivalis), streak disease Cephalosporium stripe (Cephalospori) um gramineum), cloudy disease Scald (Rhynchosporium secalis), black rust Stem rust (Puccinia graminis), barley leaf rust (Puccinia hordei), red rust Brown rust (Puccinia recondita), yellow rust Stripe rust (Puccinia) striiformis var. striiformis), smut Flag smut (Urocystis agropyri), black scab Covered smut (Ustilago hordei), naked smut Loose smut (Ustilago nuda), wheat bun (Tilletia caries, T. laevis) Barley nagusa smut (Tilletia controversa), snow rot microbacterial disease Typhula snow blight (Typhula incarnate, T. ishikariensis var. Ishikariensis), strain rot, Foot-rot (Ceratobasidium cornigerum), brown snow rot Browning rot (Pythium graminicola, P. horinouchiense, P. iwayamai, P. okanoganense, P. paddicum, P. vanterpoolii, P. volutum), rye head blight Bacterial halo blight (Pseudomonas syringae pv. Coronafaciens), black-bump disease Bacterial black node (Pseudomonas syringae pv. syringae).

  Diseases of Shiva: Dollar spot disease (Sclerotinia homoeocarpa), Fairy rings disease (Bovista dermoxantha, Conocybe apala, Lepista subnuda, Lycoperdon curtisii, L. perlatum, Marasmius oreades), pseudo-leaf rot Rhizoctonia patch (Ceratobasidium patch) ), Leaf rot, Brown patch, Large patch (Rhizoctonia solani), Rust (Puccinia zoysiae), Pythium blight (Pythium graminicola, P. periplocum, P. vanterpoolii).

  Sugarcane diseases: Leaf scorch (Stagonospora sacchari), Top rot (Fusarium moniliforme var. Majus, Gibberella fujikuroi, G. fujikuroi var. Subglutinans), Yellow rust Orange rust (Puccinia kuehnii) Brown rust (Puccinia melanocephala), smut Sugarcane smut (Sporisorium scitamineum).

  Maize diseases: sesame leaf blight, Southern leaf blight (Cochliobolus heterostrophus), soot scab, Northern leaf blight (Setosphaeria turcica), seedling blight, Seedling blight (Gibberella avenacea, Penicillium sp.), Southern rust (Puccinia polysora) ), Smut, Corn smut (Ustilago maydis), blight, Sheath blight (Thanatephorus cucumeris), root rot Browning root rot (Pythium arrhenomanes, P. graminicola).

  Banana disease: Sigatoka disease Black sigatoka (Mycosphaerella fijiensis), yellow leaf sigatoka leaf spot (Mycosphaerella musicola), Panama disease (Fusarium oxysporum f. Sp. Cubense).

  Diseases of Ginger Family Leaves: Leaf Spot (Mycosphaerella zingiberis), Ginger White Spot Leaf Spot (Phyllosticta zingiberis), Blast Blast (Pyricularia zingiberis), Stem Blight (Rhizoctonia solani), Root Rot (Pythiumul) , P. zingiberis).

  Sugar beet diseases: brown spot disease Cercospora leaf spot (Cercospora beticola), spot disease Ramularia leaf spot (Ramularia beticola), snake eye disease Leaf spot (Pleospora betae), powdery mildew Powdery mildew (Erysiphe betae), leaf rot leaf blight Root rot Root rot (Thanatephorus cucumeris), Black root disease Aphanomyces root rot (Aphanomyces cochlioides), Seedling blight Damping-off (Pleospora betae, Fusarium sp., Colletotrichum dematium, Rhizoctonia solani, Aphanomyces cochliobaryanum, Pythium)

  Diseases of spinach: Brown spot disease Leaf spot (Cercospora beticola), Spot disease Leaf mold (Cladosporium variabile), wilt disease Fusarium wilt (Fusarium oxysporum f. Sp. Spinaciae), anthracnose disease Anthracnose (Colletotrichum dematium f. Spinacia) Diseases Foot rot (Rhizoctonia solani), root rot Root rot (Aphanomyces cochlioides), downy mildew (Peronospora farinosa f. Sp. Spinaciae), withering disease Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum) , P. ultimum var. Ultimum), Bacterial leaf spot (Pseudomonas syringae pv. Spinaciae).

  Grape Diseases: Brown Spot Disease Isariopsis leaf spot (Pseudocercospora vitis), Black Mold Anthracnose (Elsinoe ampelina), Powdery Mildew Powdery mildew (Uncinula necator), Gray Mold (Botrytis cinerea), Swelling Arm (Diaporthe) kyushuensis), bud blight Bud blight (Diaporthe rudis), vine split disease Dead arm (Phomopsis viticola), late rot Ripe rot (Colletotrichum acutatum, Glomerella cingulata), rust disease Rust (Physopella ampelopsidis), downy mildew (downy mildew) Plasmopara viticola).

  Diseases of leguminous crops: Purple stain (Cercospora kikuchii), Ring bean ring spot (Cercospora zonata), peanut brown leaf spot (Mycosphaerella arachidis), groundnut black astringent leaf spot (Mycosphaerella berkeleyi), Pea brown spot disease Mycosphaerella blight (Mycosphaerella pinodes), angular leaf spot (Phaeoisariopsis griseola), pea brown spot disease Ascochyta blight (Ascochyta pisi), broad bean brown spot disease (Didymella fabae), powdery mildew (Pwdery mildew) Erysiphe pisi, Sphaerotheca fuliginea), gray mold (Botrytis cinerea), broad bean red spot disease Chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), sclerotia stem rot (Sclerotinia sclerotiorum), black root rot Crown and root rot (Calonectria ilicicola), pea blight Root rot (Fusarium arthrosporioides, F. avenaceum, F. sporotrichioides), common bean root rot Fusarium root-rot (Fusar) ium cuneirostrum), Fusarium wilt (Fusarium oxysporum f. sp. adzukicola), Stem wilt (Fusarium avenaceum, F. oxysporum f. sp. fabae), pea root rot (Fusarium solani f. sp. gregata), soybean rust, soybean rust (Phakopsora pachyrhizi), azuki rust Rust (Uromyces phaseoli var. azukicola), kidney bean rust Rust (Uromyces phaseoli var. phaseoli), rust Rust (Uromyces viciae-fabae var. viciae-fabae ), White silkworm Southern blight (Athelia rolfsii), soybean downy mildew (Peronospora manshurica), soybean stem blight Phytophthora root and stem rot (Phytophthora sojae), azuki bean Stem plague (Phytophthora vignae f. Sp. Adzukicola), soybean leaf burning Bacterial pustule (Xanthomonas campestris pv. Glycines), soybean spot bacterial disease Bacterial blight (Pseudomonas savastanoi pv. Glycinea) phaseolicola), azuki bean brown blight (Pseudomonas syringae pv. syringae).

  Hop diseases: powdery mildew (Oidium sp., Sphaerotheca intermedia), gray mold (Botrytis cinerea), wilt disease, Hop wilt (Verticillium albo-atrum), downy mildew (Pseudoperonospora humuli).

  Fig disease: yeast rot Souring (Candida sorbosa, Candida sp., Pichia kluyveri), common scab Fig scab (Sphaceloma caricae), gray mold (Botrytis cinerea), bacterial wilt Ceratocystis canker (Ceratocystis fimbriata), White root rot (Rosellinia necatrix), anthracnose Anthracnose (Glomerella cingulata), rust Rust (Phakopsora nishidana), black mold Rhizopus rot (Rhizopus stolonifer var. Stolonifer), plague White powdery rot (Phytophthora palmiv)

  Diseases of mulberry: Backy mildew (Phyllactinia moricola), shoot blight Twig blight (Hypomyces solani f. Sp. Mori, f. Sp. Pisi, Gibberella baccata), head blight Dieback (Diaporthe nomurai), white crest White root rot (Rosellinia necatrix), purple striped feather Violet root rot (Helicobasidium longisporum), red astringency Red rust (Aecidium mori), bacteriostatic bacterial disease Bacterial blight (Pseudomonas syringae pv. Mori), branch soft rot Shoot soft rot (Pectobacterium carotovorum).

  Diseases of rose: Stem blight Stem canker (Leptosphaeria coniothyrium), powdery mildew Powdery mildew (Podosphaera pannosa, Uncinuliella simulans), black star disease Black spot (Diplocarpon rosae), gray mold disease Botrytis blight (Botrytis cinerea), rust disease Rust ( Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), downy mildew (Peronospora sparsa), root gall disease Crown gall (Agrobacterium tumefaciens).

  Strawberry Diseases: Jatrobium Leaf Spot (Mycosphaerella fragariae), Powdery Mildew Powdery mildew (Sphaerotheca aphanis var. Aphanis), Gray Mold (Botrytis cinerea), Dwarf Fusarium wilt (Fusarium oxysporum f. Sp. Fragariae) ), Leaf spot leaf blight (Phomopsis obscurans), anthrax Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), plague Phytophthora rot (Phytophthora cactorum, P. nicotianae, Phytophthora sp.), Root rot stele Phytophthora fragariae).

  Diseases of loquat: Sesame color spot disease Entomosporium leaf spot (Diplocarpon mespili), gray leaf spot (Pestalotia eriobotrifolia, Pestalotiopsis funereal, P. neglecta), white root rot (Rosellinia necatrix), anthracnose disease Anthracnose ( Colletotrichum acutatum, Glomerella cingulata), Cancer canker (Pseudomonas syringae pv. Eriobotryae).

  Diseases of apples: Black spot disease Fruit spot (Mycosphaerella pomi), spotted leaf disease Alternaria blotch (Alternaria mali), black spot disease Scab (Venturia Inaequalis), ring-shaped disease Ring rot (Botryosphaeria berengeriana f. Sp. Piricola), soot spot Fly speck (Schizothyrium pomi), powdery mildew (Podosphaera leucotricha), brown spot Blotch (Diplocarpon mali), moniliosis Blossom blight (Monilinia mali), rot Valsa canker (Valsa ceratosperma), white root rot (Rosellinia necatrix), anthrax Bitter rot (Colletotrichum acutatum, Glomerella cingulata), soot spot Sooty blotch (Phyllachora pomigena), purple leaf rot Violet root rot (Helicobasidium longisporum), red rot Rust (Gymnosporangium yamadae) blight (Erwinia amylovora).

  Pear diseases: Black spot disease Black spot (Alternaria kikuchiana), Brown spot disease Brown spot (Stemphylium sp.), Black star disease Scab (Venturia nashicola), Ring rot Ring rot (Botryosphaeria berengeriana f. Sp. Piricola) Diseases Shoot blight (Botryosphaeria dothidea), powdery mildew Powdery mildew (Phyllactinia mali), blight disease Phomopsis canker (Phomopsis fukushii), keratocarcinoma Coral spot (Nectria cinnabarina), white root rot (Rosellinia) necatrix), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Rust (Gymnosporangium asiaticum), Plague Phytophthora fruit rot (Phytophthora cactorum, P. syringae), Bacterial black spot (syringae p. syringae. Fire blight (Erwinia amylovora).

  Diseases of apricot: Scab (Venturia carpophila), Zonate leaf spot (Grovesinia pruni), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Black blight Shoot blight (Coryneum sp.), Anthracnose (Gloeosporium sp., Colletotrichum acutatum), Bacterial shot hole (Xanthomonas campestris pv. Pruni).

  Plum disease: Scab (Venturia carpophila), Gray mold (Botrytis cinerea), Zonate leaf spot (Grovesinia pruni), Brown rot (Monilia mumecola, Monilinia fructicola, M. laxa) ), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Sooty blotch (Peltaster sp.), Chloranthy (Blastospora smilacis), Bacterial canker (Pseudomonas syringae pv. Morsprunorum)

  Diseases of plums: Plum pockets (Taphrina pruni), brown rot (Monilinia fructicola, M. fructigena), anthracnose (Colletotrichum acutatum), black leaf spot Bacterial leaf spot (Xanthomonas arboricola pv. Pruni).

  Peach diseases: Leaf curl (Taphrina deformans), black scab Scab (Venturia carpophila), wart skin Blister canker (Botryosphaeria berengeriana f. Sp. Perscicae), powdery mildew Powdery mildew (Podosphaera pannosa, P. tridactyla var) tridactyla), ash blight Brown rot (Monilinia fructicola, M. fructigena), homoposis rot Phomopsis rot (Phomopsis sp.), blight Cytospora canker (Leucostoma persoonii), anthracnose Anthracnose (Colletotrichum acutatum, Glomerella cing) Fruit red spot (Ellisembia sp.), Brown rust (Tranzschelia discolor), Bacterial shot hole (Xanthomonas arboricola pv. Pruni, Pseudomonas syringae pv. Syringae, Brenneria nigrifluens).

  Diseases of sweet potato: Brown perforated disease Cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), brown rot (Monilinia fructicola, M. fructigena, M. laxa), juvenile sclerotia young-fruit rot (Monilinia kusanoi), White root rot (Rosellinia necatrix), anthracnose Anthracnose (Colletotrichum acutatum, Glomerella cingulata), black mold Rhizopus rot (Rhizopus stolonifer var. Stolonifer), resinous bacterial disease Bacterial canker (Pseudomonas syringae, P. s.v. syringae, P. viridiflava).

  Diseases of cucurbit: Scab (Cladosporium cucumerinum), brown spot disease Corynespora leaf spot (Corynespora cassiicola), vine blight Gummy stem blight (Didymella bryoniae), powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp.) , Podosphaera xanthii, Sphaerotheca fuliginea), gray mold (Botrytis cinerea), sclerotia, Sclerotinia rot (Sclerotinia sclerotiorum), Fusarium wilt (Fusarium oxysporum f. Sp. Cucumerigen, f. sp. luffae, f. sp. melonis, f. sp. niveum), Fusarium basal rot (Fusarium solani f. sp. cucurbitae), Cucumber homoposis root rot (Phomopsis sp.), Root rot (Monosporascus cannonballus), pumpkin vitiligo disease Plectosporium blight (Monographella cucumerina), anthracnose Anthracnose (Colletotrichum orbiculare, Glomerella cingulata), white silkworm Southern blight (Athelia rolfsii), seedling blight Damping-off (Rhizoctytholi acearum, P. debaryanum, P. spinosum), downy mildew (Pseudoperonospora cubensis), brown rot of watermelon Brown rot (Phytophthora capsici), plague Phytophthora rot (Phytophthora capsici, P. cryptogea, P. melonis, P. melonis, P. ), Cotton rot Pythium fruit rot (Pythium aphanidermatum), Bacterial fruit blotch (Acidovorax avenae subsp. Citrulli), brown spot Bacterial spot (Xanthomonas campestris pv. Cucurbitae), Marginal blight (Pseudomonas marginalis pv. Marginalis, P. viridiflava), Angular leaf spot (Pseudomonas syringae pv. Lachrymans).

  Diseases of chestnut: Endothia canker (Cryphonectria parasitica), Anthracnose (Glomerella cingulata).

  Diseases of cruciferous vegetables: white spot (Pseudocercosporella capsellae), black leg disease (Leptosphaeria maculans), black spot disease Alternaria leaf spot (Alternaria brassicae, A. brassicicola, A. japonica), black soot disease Alternaria sooty spot (Alternaria brassicicola), Wasabi ink-filled black leg (Phoma wasabiae), gray mold (Botrytis cinerea), rape snow mold (Sclerotinia nivalis, Typhula japonica, T. incarnate, T. ishikariensis var. ishikariensis), mycorrhizal disease Sclerotinia rot (Sclerotinia sclerotiorum), yellow yellow (Fusarium oxysporum f. sp. conglutinans), Japanese radish yellow yellow (Fusarium oxysporum f. sp. raphani), Japanese black spot disease Verticillium black spot disease (Verticillium black spot disease) Verticillium albo-atrum, V. dahliae), Chinese cabbage yellowing disease Yellows (Verticillium dahliae), cabbage verticillium wilt Verticillium wilt (Verticillium longisporum), anthracnose Anthracnose (Co lletotrichum dematium, C. destructivum, C. higginsianum), Damping-off (Rhizoctonia solani), clubroot (Plasmodiophora brassicae), white rust (Albugo macrospora), wasabi white rust (Albugo wasabiae), Komatsuna downy mildew Downy mildew (Hyaloperonospora brassicae), Wasabi downy mildew (Peronospora alliariae-wasabi), downy mildew (Peronospora parasitica), cabbage seedling disease Damping-off (Pythium buismaniae) , P. zingiberis, Rhizoctonia solani), withering disease Damping-off (Pythium sp.), Black rot Black rot (Xanthomonas campestris pv. Campestris), broccoli flower rot, Head rot (Pseudomonas fluorescens, P. viridiflava, Pectobacterium car ), Bacterial black spot (Pseudomonas syringae pv. Maculicola), Bacterial soft rot (Pectobacterium carotovorum, P. wasabiae).

  Papaya disease: soft rot Phytophthora blight (Phytophthora nicotianae).

  Diseases of okra: Leaf leaf mold (Pseudocercospora abelmoschi), fruit black spot disease Alternaria rot (Alternaria alternata), ring rot pod spot (Phoma exigua var. Exigua), powdery mildew Powdery mildew (Leveillula taurica), gray Mold mold Gray mold (Botrytis cinerea), black root disease Black root rot (Thielaviopsis basicola), seedling blight Damping-off (Rhizoctonia solani, Pythium ultimum var. Ultimum, Pythium sp.), Leaf blight (Pseudomonas cichorii, P) viridiflava).

  Mango disease: Anthracnose (Colletotrichum acutatum, Glomerella cingulata).

  Diseases of citrus: Yellow spot Greasy spot (Mycosphaerella citri, M. horii), common scab Scab (Elsinoe fawcettii), black rot Black rot (Alternaria citri), green mold common green mold (Penicillium digitatum), blue mold disease Blue mold (Penicillium italicum), gray mold (Botrytis cinerea), black spot Melanose (Diaporthe citri), small sunspot Melanose like blemish (Alternaria citri, Diaporthe rudis), white coat rot (Rosellinia necatrix), Anthracnose (Glomerella cingulata), brown rot (Phytophthora citricola, P. citrophthora, P. nicotianae, P. palmivora), scab disease Citrus canker (Xanthomonas citri subsp. Citri).

  Diseases of kiwifruit: Sooty spot (Pseudocercospora actinidiae), soft rot of fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Gray mold (Botrytis cinerea), white root rot (white root rot) Rosellinia necatrix), Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Bacterial bacterial disease Bacterial blossom blight (Pseudomonas marginalis pv. Marginalis, P. syringae pv. Syringae, P. viridiflava) actinidiae).

  Oyster diseases: angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae), black spot (Fusicladium levieri), soot spot Fly speck (Schizothyrium pomi), powdery mildew Powdery mildew (Phyllactinia kakicola), gray mold (Botrytis cinerea), black leaf spot (Discostroma sp.), Anthracnose Anthracnose (Glomerella cingulata).

  Diseases of blueberries: Gray mold (Botrytis cinerea), Valdensia leaf blight (Valdensia heterodoxa).

  Tea diseases: Brown round spot (Cercospora chaae, Pseudocercospora ocellata), Anthracnose (Discula theae-sinensis), Ring blight Gray blight (Pestalotiopsis longiseta, P. theae), White root rot (Rosellinia necatrix), leaf blight Brown blight (Glomerella cingulata), net blast Net blister blight (Exobasidium reticulatum), blast Blister blight (Exobasidium vexans), black leaf rot Black rot (Ceratobasidium sp.) Disease Bacterial shoot blight (Pseudomonas syringae pv. Theae).

  Perilla disease: spot disease Corynespora leaf spot (Corynespora cassiicola), rust Rust (Coleosporium plectranthi).

  Diseases of sesame: Stem rot (Athelia rolfsii), Bacterial wilt (Ralstonia solanacearum), bacterial leaf spot (Pseudomonas syringae pv. Sesami).

  Diseases of sweet potato: stem rot (Fusarium oxysporum f. Sp. Batatas, F. solani), black spot black rot (Ceratocystis fimbriata), purple leaf rot Violet root rot (Helicobasidium longisporum), soft rot Soft rot ( Rhizopus stolonifer var. Stolonifer, R. tritici), withering disease Soil rot (Streptomyces ipomoeae).

  Tomato diseases: Leaf mold (Mycovellosiella fulva), mold mold Cercospora leaf mold (Pseudocercospora fuligena), brown ring disease Corynespora target spot (Corynespora cassiicola), ring blight disease Early blight (Alternaria solani), leaf spot disease spot (Stemphylium lycopersici, S. solani), brown root rot (Pyrenochaeta lycopersici), powdery mildew, Powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), gray mold (Botrytis cinerea), fungus Stem rot (Sclerotinia sclerotiorum), Fusarium wilt (Fusarium oxysporum f. Sp. Lycopersici), Crown and root rot (Fusarium oxysporum f. Sp. Radicis-lycopersici), Verticillium wilt Verticillium dahliae), white silk disease Southern blight (Athelia rolfsii), seedling blight Damping-off (Rhizoctonia solani, Pythium vexans), plague Late blight (Phytophthora infestans), scab disease Bacterial canker (Clavibacter michig) anensis subsp. michiganensis), bacterial wilt (Ralstonia solanacearum), bacterial spot Bacterial spot (Xanthomonas campestris pv. vesicatoria), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Eggplant diseases: Leaf mold (Mycovellosiella nattrassii), brown spot disease (Paracercospora egenula), black blight Black blight (Corynespora cassiicola), brown spot Early blight (Alternaria solani), powdery mildew Powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), gray mold (Botrytis cinerea), mycorrhizal disease Stem rot (Sclerotinia sclerotiorum), half blight (Fusarium oxysporum f. Sp. Melongenae), half body wilt wilt verticium Verticillium dahliae), brown spot disease (Phomopsis vexans), white silkworm Southern blight (Athelia rolfsii), seedling blight Damping-off (Rhizoctonia solani), brown rot Brown rot (Phytophthora capsici), plague late blight ( Phytophthora infestans), bacterial wilt (Ralstonia solanacearum), brown leaf blight Necrotic leaf spot (Pseudomonas cichorii).

  Potato Diseases: Summer blight Early blight (Alternaria solani), Dry rot Dry rot (Fusarium oxysporum, Fusarium solani f. Sp. Eumartii, f. Sp. Radicicola), Anthracnose (Colletotrichum coccodes), Black scurf (Thanatephorus cucumeris), powdery scab, Powdery Scab (Spongospora subterranea f. Sp. Subterranea), plague Late blight (Phytophthora infestans), ring rot Ring rot (Clavibacter michiganensis subsp. Sepedonicus), scab Scab (Streptomyces sp) Bacterial wilt (Ralstonia solanacearum), black leg (Dickeya dianthicola, Pectobacterium atrosepticum, P. carotovorum), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Diseases of pepper peppers: spotted diseases Frogeye leaf spot (Cercospora capsici), black blight Corynespora blight (Corynespora cassiicola), white spot disease Stemphyrium leaf spot (Stemphylium lycopersici), powdery mildew Powdery mildew (Leveillula taurica) mold (Botrytis cinerea), mycorrhizal disease Sclerotinia rot (Sclerotinia sclerotiorum), wilt Fusarium wilt (Fusarium oxysporum), anthracnose Anthracnose (Colletotrichum acutatum, C. capsici, C. nigrum), white silk disease Southern blight (Athelia) Damping-off (Rhizoctonia solani), Phytophthora blight (Phytophthora capsici), Bacterial wilt (Ralstonia solanacearum), Bacterial spot disease (Xanthomonas campestris pv. Vesicaacter), soft rot Brot Pectobacterium carotovorum).

  Tobacco disease: Red spot disease Brown spot (Alternaria alternata), back fracture Sore shin (Rhizoctonia solani), plague Black shank (Phytophthora nicotianae), blight Bacterial wilt (Ralstonia solanacearum).

  Celery disease: Spot blight Early blight (Cercospora apii), leaf blight Late blight (Septoria apiicola), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Mitsuba's diseases: Sclerotinia rot (Sclerotinia sclerotiorum), blight (Fusarium oxysporum f. Spii), rust Rust (Puccinia tokyensis), blight (Rhizoctonia solani), downy mildew (Plasmopara) nivea), root rot (Pythium aphanidermatum, P. apleroticum, Pythium sp.).

  Diseases of carrots: Spot disease Cercospora blight (Cercospora carotae), black leaf blight Leaf blight (Alternaria dauci), black spot disease Alternaria black rot (Alternaria radicina), powdery mildew Powdery mildew (Erysiphe heraclei), mycorrhizal disease Sclerotinia rot (Sclerotinia minor, S. sclerotiorum), dry rot Dry rot (Fusarium solani f. Sp. Radicicola, Gibberella avenacea), purple coat feather Violet root rot (Helicobasidium longisporum), white silkworm Southern blight (Athelia rolfsii), white Silk blight Southern blight (Athelia rolfsii), root rot Damping-off (Rhizoctonia solani), blot rot Brown blotted root rot (Pythium sulcatum), root gall (Agrobacterium tumefaciens), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Diseases of parsley: Leaf spot (Cercospora apii), powdery mildew Powdery mildew (Erysiphe heraclei), plague (Phytophthora nicotianae), soft rot Bacterial soft rot (Pectobacterium carotovorum).

  Diseases of crabs: common scab Spot anthracnose (Elsinoe araliae), wilt disease (Phytophthora cactorum).

  Diseases of Udo: Black spot disease spot spot (Alternaria panax, Alternaria sp.), Sclerotia disease Sclerotinia rot (Sclerotinia sclerotiorum), wilt disease Verticillium wilt (Verticillium dahliae, V. nigrescens), white silk disease Southern blight (Athelia rolfsii) The plague Phytophthora rot (Phytophthora cactorum).

  Lettuce diseases: Gray mold (Botrytis cinerea), sclerotia Stem rot (Sclerotinia sclerotiorum), root rot Root rot (Fusarium oxysporum f. Sp. Lactucae), bottom rot Bottom rot (Rhizoctonia solani) Downy mildew (Bremia lactucae), Bacterial spot (Xanthomonas axonopodis pv. Vitians), Bacterial rot (Pseudomonas cichorii, P. marginalis pv. Marginalis, P. viridiflava), Bacterial soft carrot (Pectobacterium) ).

  Diseases of chrysanthemum: black spot disease spot spot (Septoria chrysanthemella), brown spot disease leaf blight (Septoria obesa), flower rot ray blight (Didymella chrysanthemi), powdery mildew powdery mildew (Erysiphe cichoracearum var. Cichoracearum), gray mold disease Botrytis blight (Botrytis cinerea), sclerotia Stem rot (Sclerotinia sclerotiorum), half body wilt Wilt (Verticillium dahliae), brown rust Rust (Phakopsora artemisiae), white rust Rust (Puccinia horiana), black rust Rust (Puccinia) tanaceti var. tanaceti), flower blight Petal blight (Itersonilia perplexans), white silk disease Southern blight (Athelia rolfsii), blight Root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), downy mildew (Peronospora danica) Phytophthora rot (Phytophthora cactorum, Phytophthora sp.), Crown gall (Agrobacterium tumefaciens), Bacterial wilt (Ralstonia solanacearum), Bacterial stem rot (Pectobacterium c) arotovorum).

  Diseases of syringae: leaf blight Leaf blight (Cercospora chrysanthemi), anthracnose Anthracnose (Colletotrichum acutatum), downy mildew (Peronospora chrysanthemi-coronarii).

  Sunflower diseases: brown spot disease (Septoria helianthi), black spot leaf spot (Alternaria helianthi), powdery mildew (Powdery mildew) (Erysiphe cichoracearum, Golovinomyces cichoracearum var. Latisporus, Oidium sp., Podosphaera fusca) Gray mold (Botrytis cinerea), mycorrhizal disease Sclerotinia rot (Sclerotinia sclerotiorum), seedling blight Root and stem rot (Rhizoctonia solani), downy mildew (Plasmopara halstedii), spotted bacterial disease Bacterial leaf spot (Pseudomonas syringae pv) helianthi), cavity disease (Pectobacterium carotovorum).

  Buffalo disease: Verticillium wilt (Verticillium dahliae), white silkworm Southern blight (Athelia rolfsii).

Burdock disease: Black spot disease (Phoma exigua var. Exigua), powdery mildew (Powdery mildew (Podosphaera fusca)), black streak disease (Black streak (Itersonilia perplexans)), black bruise Black scurf (Rhizoctonia solani), root rot (Pythium irregulare), Bacterial spot (Xanthomonas campestris pv. Nigromaculans).
However, plant diseases that can be controlled using the compounds of the present invention are not limited to these.

  That is, the composition of the present invention and the method of the present invention are also extremely effective against pests that have developed resistance to existing insecticides such as organophosphorus compounds, carbamate compounds, or pyrethroid compounds. Eyes (Coleoptera), Hymenoptera (Hymenoptera), Lepidoptera (Lepidoptera), Diptera (Flyes), Common lepidoptera (Thysanoptera), Hemiptera (Heroptera and Hemiptera), Straight Insects such as eyes (Battacidae), reticulates (roaches), isoptera (Termites), slime (Coleoptera), crustacea (Coleoptera), crustaceans, eucentipede, ishimde Pests belonging to the order of mites and gastropods, such as polypods such as eyes and geese, subcarids (Acaridaceae), subcarids (Acaridaceae, Dustaceae, Acaridaceae, Acaridaceae, Acaridaceae) Can be effectively controlled at a low concentration. On the other hand, the composition of the present invention and the method of the present invention have extremely adverse effects on mammals, fish, crustaceans and beneficial insects (useful insects such as honeybees, bumblebees, natural enemies such as honeybees, wasps, mistletoe, and stink bugs). It has few useful features.

  “Plant” in this specification refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, appreciation plants that love their form and shape, or planting in parks, streets, etc. It means vascular plant (Tracheophyta). Specific examples include the following plants, but are not limited thereto.

  Pinaceae plants belonging to Pinaceae, such as Japanese red pine (Pinus densiflora), European red pine Scots Pine (Pinus sylvestris), Japanese black pine (Pinus thunbergii).

Pepper (Piper nigrum) such as Pepperaceae (Piperaceae), Avocado Avocado (Persea americana) such as Lauraceae magnolias (magnoliids),
Konjac (Amorphophallus konjac), taro edodee (Colocasia esculenta) and other taros (Araceae), Chinese yam (yioscorea batatas), yam Japanese yam (Dioscorea japonica) and other yam (Dioscoreacesum var) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Leek Welsh onion (Allium fistulosum), Garlic Garlic (Allium sativum), Chives Chives (Allium schoenoprasum), Asatsuchi Chive (Allium schoenoprasum) Japanese leek Oriental garlic (Allium tuberosum), spring onion Scallion (Allium x wakegi), etc. Alliaceae, asparagus Asparagus (Asparagus officinalis), etc. (Elaeis guineensis) and other palms (Arecaceae) arecaidea (Arecoideae), na Date palm (Phoenix dactylifera) and other palms (Arecaceae) Talipot subfamily (Coryphoideae), pineapples Pineapple (Ananas comosus) and other pineapples (Bromeliaceae), rice Rice (Poryae sativa) and other poaceae Family (Ehrhartoideae), bentgrass Bent grass (Agrostis spp.), Bluegrass Blue grass (Poa spp.), Barley Barley (Hordeum vulgare), wheat Wheat (Triticum aestivum, T. durum), rye Rye (Secale cereale), etc. Poaceae Strawberry subfamily (Pooideae), Googyushiba Bermuda grass (Cynodon dactylon), Shiba Grass (Zoysia spp.), Etc. Sorgum (Sorghum bicolor), Corn Corn (Zea mays), etc. Gramineae (Poaceae) Millet subfamily (Panicoideae), Banana Banana (Musa spp.), Etc. Monocots belonging to Zingiberaceae, such as Musaceae, Myoga (Zingiber mioga), Ginger (Zingiber officinale) and the like.

  Lotus root (Nelumbo nucifera), etc. Lotus family (Nelumbonaceae), groundnut Peanut (Arachis hypogaea), chickpea (Chicpea (Cicer arietinum)), lentil Lentil (Lens culinaris), pea Pea (Pisum sativum), broad bean Bia bea , Soybean Soybean (Glycine max), common bean (Phaseolus vulgaris), adzuki bean (Vigna angularis) adzuki bean (Vigna angularis), legume (Fabaceae) such as cowpea (Vigna unguiculata), Chopaceae (Cannabaceae) such as hop Hop (Humulus lupulus) ), Fig Tree (Ficus carica), Mulberry (Morus spp.), Etc. (Moraceae), Jujube (Ziziphus jujuba), etc. (Rhamnaceae), Strawberry Strawberry (Fragaria), Rose Rose (Rosa) spp.) and other Rosaceae (Rosaceae) subfamily (Rosoideae), loquat Japanese loquat (Eriobotrya japonica), apple Apple (Malus pumila), pear European Pear ( Pyrus communis), pear Nashi Pear (Pyrus pyrifolia var. Culta) and other roses (Rosaceae) pear subfamily (Maloideae), peach Peach (Amygdalus persica), apricot Apricot (Prunus armeniaca), sweet cherry (Prunus avium), prunes Roses such as Prune (Prunus domestica), Almond Almond (Prunus dulcis), Japanese plum Apricot (Prunus mume), Japanese plum Plum (Prunus salicina), Oshima cherry (Cerasus speciosa), Yoshino cherry (Cerasus x yedoensis'Somei-yoshino ') (Rosaceae) Cherry subfamily (Prunoideae), Tougan Winter melon (Benincasa hispida), Watermelon Watermelon (Citrullus lanatus), Yugao Bottle gourd (Lagenaria siceraria var. Hispida), Loofah Luffa (Luffa cylindrica), Pumpkin Pumpkin (Pumpkin) , Zucchini (Cucurbita pepo), Bitter melon (Momordica charantia var. Pavel), Melon Muskmelon (Cucumis melo), Oriental pi culingis melon (Cucumis melo var. conomon), cucumber Oriental melon (Cucumis melo var. makuwa), cucumber Cucumber (Cucumis sativus) and other Cucurbitaceae, chestnut Japanese Chestnut (Castanea crenata) and other beech (Fagaceae) Walnut (Juglans spp.) And other walnuts (Juglandaceae), cashew nut Cashew (Anacardium occidentale), mango Mango (Mangifera indica), pistachio Pistachio (Pistacia vera), etc. ) Etc. (Rutaceae) Henruda subfamily (Rutoideae), Daidai Bitter orange (Citrus aurantium), Lime Lime (Citrus aurantifolia), Hassaku Hassaku orange (Citrus hassaku), Yuzu Yuzu (Citrus junos), Lemon Lemon (Citrus limon) ), Natsumikan (Citrus natsudaidai), Grapefruit (Citrus x paradisi), Orange Orange (Citrus sinensis) ), Kabosu Kabosu (Citrus sphaerocarpa), Sudachi Sudachi (Citrus sudachi), Ponkan Mandarin Orange (Citrus tangerina), Satsuma (Citrus unshiu), Kumquat Kumquat (Fortunella spp.), Etc. (Rutaceae) Aurantioideae), Horseradish (Armoracia rusticana), Mustard (Brassica juncea), Takana Takana (Brassica juncea var. Integrifolia), Brassica rapeseed (Brassica napus), Cauliflower Cauliflower (Brassica oleracea var) oleracea var. capitata), brussels sprout (Brassica oleracea var. gemmifera), broccoli (Brassica oleracea var. italica), green pak choi (Brassica rapa var. chinensis), Nozawana (varassakapaura) Napa cabbage (Brassica rapa var. Nippo-oleifera), Mizuna Potherb Mustard (B rasposica rapa var. nipposinica), Chinese cabbage Napa cabbage (Brassica rapa var. pekinensis), Komatsuna Turnip leaf (Brassica rapa var. perviridis), turnip Turnip (Brassica rapa var. rapa), Arugula Garden rocket (Eruca vesicaria) Raphanus sativus var. Longipinnatus), Brassicaaceae such as Wasabi (Wasabia japonica), Papaya (Caricaceae) such as Papaya (Carica papaya), Okra Okra (Abelmoschus esculentus), Cotton Cottonp. , Cacao (Theobroma cacao) such as Malvaceae, Grapes Grape (Vitis spp.) Grapes (Vitaceae), sugar beet Sugar beet (Beta vulgaris ssp. Vulgaris var. Altissima), table beet Table beet (Beta vulgaris ssp. vulgaris var. vulgaris), Amaranthaceae such as spinach (Spinacia oleracea), Polygonaceae such as buckweat (Fagopyrum esculentum) , Kaki Persimmon (Diospyros kaki) and other oysters (Ebenaceae), Cha Tea plant (Camellia sinensis) and other camellia (Theaceae), Kiwifruit Kiwifruit (Actinidia deliciosa, A. chinensis) and other matabiaceae (Actinidiaceae), Blueberry (Vaccinium spp.), Cranberry Cranberry (Vaccinium spp.) And other azaleas (Ericaceae), Coffee tree Coffee plants (Coffea spp.) And other Rubiaceae, lemon balm Lemon balm (Melissa officinalis), mint Mint ( Mentha spp.), Basil Basil (Ocimum basilicum), perilla Shiso (Perilla frutescens var. Crispa), egoma (Perilla frutescens var. Frutescens), sage Common Sage (Salvia officinalis), thyme Thyme (Thymus spp.) (Lamiaceae), Sesame (Pedaliaceae) such as Sesame (Sesamum indicum), Oleaceae such as Olive Olive (Olea europaea), Sweet potato (I pomoea batatas), convolvulaceae, tomato Tomato (Solanum lycopersicum), eggplant Eggplant (Solanum melongena), potato Potato (Solanum tuberosum), chili pepper Chili pepper (Capsicum annuum), bell pepper Bell pepper (Capsicum angrosum var. '), Solanum (Solanaceae) such as tobacco Tobacco (Nicotiana tabacum), Celery (Apium graveolens var. Dulce), Coriander (Coriandrum sativum), Japanese honeywort (Cryptotaenia Canadensis subsp. Japonica), carrot Carrot (Daucus carrot (Daucus subsp. sativus), parsley Parsley (Petroselium crispum), Italian parsley Italian parsley (Petroselinum neapolitanum) and other seriaceae (Apiaceae), Udo Udo (Aralia cordata), arachnid (Aralia elata) and other scallops (Araliaceich), artichoke (Cynara scolymus) and other Asteraceae, Carduoideae, Chrysanthemum Chicory (Cichorium intybus), Lettuce Lettuce (Lactuca sativa), etc. Authentic dicots (eudicots) belonging to Asteraceae and Asteraceae such as Fuki (Petasites japonicus) and Burdock (Arctium lappa).

  In addition, “plant” in the present specification refers to an HPPD inhibitor such as isoxaflutol, an ALS inhibitor such as imazetapyr and thifensulfuron / methyl, an EPSP synthase inhibitor such as glyphosate, and a glutamine synthase such as glufosinate. Inhibitors, acetyl-CoA carboxylase inhibitors such as cetoxidim, PPO inhibitors such as flumioxazin, and resistance to herbicides such as bromoxynil, dicamba and 2,4-D are imparted by classical breeding methods and gene recombination techniques. Plants are also included.

  Examples of “agricultural and horticultural plants” that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. It has already been sold under the product name>.

  Similarly, there are soybeans resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already sold under the trade name STS soybeans. Similarly, SR corn and the like are examples of agricultural and horticultural plants to which resistance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Agro-horticultural plants tolerated by acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc.Natl.Acad .Sci. USA) 87, 7175-7179 (1990). A mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005). By introducing a mutation into the plant acetyl-CoA carboxylase by introducing into the plant by resistance or resistance, a plant resistant to the acetyl-CoA carboxylase inhibitor can be produced. Furthermore, a nucleic acid introduced with a base substitution mutation represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into a plant cell to produce a crop (acetyl CoA carboxylase / herbicide). Plants that are resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created by inducing site-specific amino acid substitution mutations in the target) gene.

  Examples of agricultural and horticultural plants imparted with resistance by genetic recombination technology include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties, Roundup Ready (registered trademark), Aglisher GT ( (Agriculture GT) <registered trademark> and the like. Similarly, there are corn, soybean, cotton and rapeseed varieties that are resistant to glufosinate by genetic recombination technology, and are already sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynyl-resistant cotton by gene recombination technology is already sold under the trade name BXN.

  The “agricultural and horticultural plant” includes a plant that can synthesize, for example, a selective toxin known in the genus Bacillus using a gene recombination technique.

  Examples of insecticidal toxins expressed in such transgenic plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab, Cry1Ac derived from Bacillus thuringiensis, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; scorpion toxin, spider toxin, bee toxin or insect specific Toxins produced by animals such as neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatins, papain inhibitors; ricin, tow Ribosome-inactivating protein (RIP) such as Rokoshi-RIP, abrin, saporin, bryodin; Steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA Reductase; ion channel inhibitors such as sodium channel inhibitor and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase;

  Moreover, as toxins expressed in such genetically modified plants, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxin proteins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins Hybrid toxins, partially defective toxins, and modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.

  Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. It is described in the patent literature. Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests.

Also, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include Yieldgard (registered trademark) (a corn variety that expresses Cry1Ab toxin), YieldGuard rootworm (registered trademark) (a corn variety that expresses Cry3Bb1 toxin), YieldGuard Plus (registered trademark) (a corn variety expressing Cry1Ab and Cry3Bb1 toxin), Herculex I (registered trademark) (phosphino for conferring resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing Tricine N-acetyltransferase (PAT)), NuCOTN33B <registered trademark> (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollgard I) <registered trademark> (cotton varieties expressing Cry1Ac toxin), Bolgard II (Bollgard II) <registered trademark> (cotton varieties expressing Cry1Ac and Cry2Ab toxins), Bolgard III (Bollgard III) <registered trademark> (Cotton variety expressing Cry1Ac, Cry2Ab, and VIP3A toxin) VIPCOT <registered trademark> (cotton variety expressing VIP toxin), WideStrike <registered trademark> (cotton variety expressing Cry1Ac and Cry1F toxin), New Leaf (registered trademark) (a potato variety expressing Cry3A toxin), Natureguard AGuresure GT Advantage (NatureGard (registered trademark)) <Agriureure (registered trademark)> GT Ad antage) (GA21 glyphosate resistance trait), Agri Shure CB Advantage (Agrisure <R> CB Advantage) (Bt11 corn borer (CB) trait), the protector (Protecta) <R> and the like.
The thing to which the structure | tissue with respect to aphids, such as soybean which introduce | transduced the Rag1 (Resistance Aphid Gene 1) gene was provided, is also contained. RNAi is an example of a gene recombination technique that provides nematode resistance.

  The plants include those that have been imparted with the ability to produce anti-pathogenic substances having a selective action using genetic recombination techniques.

  Examples of anti-pathogenic substances include PR proteins (described in PRPs, EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) And the like, which are produced by microorganisms such as those described in WO 03/000906). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

  The plants include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted using genetic recombination techniques. Examples include VISTIVE <(R)> (low linolenic soybeans with reduced linolenic content) or high-lysine (high wheel) corn (corn with increased lysine or oil content).

  In addition, the above-mentioned classic herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, anti-pathogenic substance production genes, oil component modification and amino acid content enhancement traits Combined stack varieties are also included. Also included are plants into which RNAi technology has been introduced.

  In the composition of the present invention, one or two active compounds I as the first active ingredient and one or more active compounds II as the second active ingredient can be used as a mixture as it is. Are usually mixed with a suitable solid carrier or liquid carrier, and if necessary, surfactants, penetrants, spreading agents, thickeners, antifreezing agents, binders, anti-caking agents, disintegrating agents, antifoaming agents. , Antiseptic and anti-degradation agent added, soluble concentrate, emulsion (emulsifiable concentrate), wettable powder, water soluble powder, water dispersible granule , Water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule , Tablets and It can be put into practical use in resistance gels (emulsifiable gel) like any dosage form of the formulation. Further, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.

  Examples of the solid carrier include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, siegrite, and allophane. Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example, natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay and calcined diatomaceous earth Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose , And Sugars such as sugar and lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic materials such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork flour, corn cobs, walnut shells and Examples include plants such as tobacco stalks, fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.) and fertilizers.

Examples of the liquid carrier include xylene, alkyl (C ₉ or C ₁₀ etc.) benzene, phenyl xylyl ethane and alkyl (C ₁ or C ₃ etc.) naphthalene and other aromatic hydrocarbons, machine oil, normal paraffin, isoparaffin and Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol Ethers such as ethyl monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and γ-butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialkyl esters of glutamic acid, adipine esters such as dialkyl ester and dialkyl phthalate esters, N- alkyl (C _1, C ₈ or C _12, etc.) acid amide pyrrolidone, soybean oil, linseed oil, rapeseed oil, coconut oil, such as cottonseed oil and castor oil Examples include fats and oils, dimethyl sulfoxide and water.

  These solid and liquid carriers may be used alone or in combination of two or more.

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyls Rufosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxyethylene (Mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg polyacrylate, polymaleate and maleate) Copolymer of acid and olefin, etc.) and anionic surfactants such as polystyrene sulfonate, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric interfaces such as amino acid type and betaine type Sexual agents, silicone-based surfactants and fluorinated surfactants.

  The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

  Next, formulation examples of preparations when using the composition of the present invention are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight, and “active ingredient compound” means active compound I as the first active ingredient and active compound II as the second active ingredient in the composition of the present invention. It is a generic name.

[Wettable powder]
Active ingredient compound 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts Others include, for example, anti-caking agents and decomposition inhibitors.

[Emulsifiable concentrate]
Active ingredient compound 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.

[Suspension concentrate]
Active ingredient compound 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners.

[Granular wettable powder (water dispersible granule)]
Active ingredient compound 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.

[Soluble concentrate]
Active ingredient compound 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.

[Granule]
Active ingredient compound 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.

[Dustable powder]
Active ingredient compound 0.01 to 30 parts Solid support 65 to 99.99 parts Others 0 to 5 parts Other examples include a drift inhibitor and a decomposition inhibitor.

  Next, although the example of an agrochemical formulation which uses this invention composition as an active ingredient is shown more concretely, this invention is not limited to these.

  In the following formulation examples, “parts” means parts by weight.

[Formulation Example 1] wettable powder compound (1-001) 10 parts Compound No. A01 10 parts Pyrophyllite 76 parts Solpol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Co., Ltd. trade name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.

[Composition Example 2] Emulsifiable concentrate
Compound (1-001) 3 parts Compound No. B01 2 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industries, Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.

[Composition Example 3] Suspension concentrate
Compound (1-001) 15 parts Compound No. C01 10 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation)
Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name)
Xanthan gum 0.2 parts Water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.

[Formulation Example 4] Granule wettable powder (water dispersible granule)
Compound (1-001) 40 parts Compound No. D01 35 parts Hytenol NE-15 5 parts (anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 5] Granule
Compound (1-001) 3 parts Compound No. E01 2 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to form granules.

[Formulation 6] dustable powder
Compound (1-001) 2 parts Compound No. F01 1 part Carplex # 80D 0.5 part (white carbon: Shionogi & Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts or more uniformly mixed and pulverized to obtain a powder.

  In use, the wettable powder, emulsion, flowable powder and granular wettable powder are diluted 1 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha).

  In the present invention, the composition of the present invention containing the active compound I as the first active ingredient and the active compound II as the second active ingredient can be formulated and used as described above, A drug containing each of active compound I and active compound II as active ingredients is prepared separately, and these drugs are used or treated or applied at the same time or close to each other in time to obtain a synergistic excellent control effect. You can also. In addition, when applying in close proximity in time, it is desirable to perform the next spraying after the sprayed drug is sufficiently dried, depending on the controlling means and the target disease to be controlled.

[Test example]
Next, in order to clarify the usefulness of the present invention, it will be specifically described in the following efficacy test examples, but the present invention is not limited to these.

[Test Example 1] Efficacy test against Japanese pearl moth The compounds listed in Tables 1 to 3 and the active ingredients listed in Tables 4 to 29 were prepared according to the formulation examples. The preparation was diluted with water containing a spreading agent to prepare a chemical solution having a predetermined concentration. Cabbage leaves were put into the chemical solution and immersed for 10 seconds. Next, one processed cabbage leaf was transferred to a 7 cm petri dish with filter paper and dried in air. After air-drying, 7 larvae of the long-horned beetle were released per petri dish. After releasing, the petri dish was housed in a constant temperature room at 25 ° C. The number of larvae killed 6 days after the treatment was investigated, and the mortality rate was determined from the following formula. In addition, the test was performed by 2 continuous systems.

Mortality (%) = dead insects / test insects x 100
Tables 30 to 41 show the results regarding the death rate of each chemical solution.

  The synergistic effect can be calculated from the mortality rate for each chemical concentration using the Colby method (Colby SR 1967, Weeds 15, 20-22). The calculation method is as follows.

E = X + Y-XY / 100
X: observed value of agent A at x concentration (death rate)
Y: Observed value of B agent at y concentration (death rate)
E: Expected death rate (expected value) during mixed treatment of agent A and agent B
If the results (death rate) obtained in Test Examples 1 to 7 are larger than the expected value, the synergistic effect is observed. It is analyzed as an additive action.
[Table 30]
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 300 100
1-002 300 100
1-003 300 100
1-004 300 100
1-005 300 100
1-006 300 100
1-007 300 100
1-008 300 100
1-009 300 100
2-001 300 100
3-001 300 100
S01 3 100
U02 3 100
V01 5 100
V02 5 100
V03 10 100
W10 10 100
X02 30 100
X05 10 100
Y01 20 100
Z08 5 100
Z12 20 100
Z14 10 100
―――――――――――――――――――――
[Table 31]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + S01 300 + 3 100 100
1-001 + U02 300 + 3 100 100
1-001 + V01 300 + 5 100 100
1-001 + V02 300 + 5 100 100
1-001 + V03 300 + 10 100 100
1-001 + W10 300 + 10 100 100
1-001 + X02 300 + 30 100 100
1-001 + X05 300 + 10 100 100
1-001 + Y01 300 + 20 100 100
1-001 + Z08 300 + 5 100 100
1-001 + Z12 300 + 20 100 100
1-001 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 32]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + S01 300 + 3 100 100
1-002 + U02 300 + 3 100 100
1-002 + V01 300 + 5 100 100
1-002 + V02 300 + 5 100 100
1-002 + V03 300 + 10 100 100
1-002 + W10 300 + 10 100 100
1-002 + X02 300 + 30 100 100
1-002 + X05 300 + 10 100 100
1-002 + Y01 300 + 20 100 100
1-002 + Z08 300 + 5 100 100
1-002 + Z12 300 + 20 100 100
1-002 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 33]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + S01 300 + 3 100 100
1-003 + U02 300 + 3 100 100
1-003 + V01 300 + 5 100 100
1-003 + V02 300 + 5 100 100
1-003 + V03 300 + 10 100 100
1-003 + W10 300 + 10 100 100
1-003 + X02 300 + 30 100 100
1-003 + X05 300 + 10 100 100
1-003 + Y01 300 + 20 100 100
1-003 + Z08 300 + 5 100 100
1-003 + Z12 300 + 20 100 100
1-003 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 34]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + S01 300 + 3 100 100
1-004 + U02 300 + 3 100 100
1-004 + V01 300 + 5 100 100
1-004 + V02 300 + 5 100 100
1-004 + V03 300 + 10 100 100
1-004 + W10 300 + 10 100 100
1-004 + X02 300 + 30 100 100
1-004 + X05 300 + 10 100 100
1-004 + Y01 300 + 20 100 100
1-004 + Z08 300 + 5 100 100
1-004 + Z12 300 + 20 100 100
1-004 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 35]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + S01 300 + 3 100 100
1-005 + U02 300 + 3 100 100
1-005 + V01 300 + 5 100 100
1-005 + V02 300 + 5 100 100
1-005 + V03 300 + 10 100 100
1-005 + W10 300 + 10 100 100
1-005 + X02 300 + 30 100 100
1-005 + X05 300 + 10 100 100
1-005 + Y01 300 + 20 100 100
1-005 + Z08 300 + 5 100 100
1-005 + Z12 300 + 20 100 100
1-005 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 36]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + S01 300 + 3 100 100
1-006 + U02 300 + 3 100 100
1-006 + V01 300 + 5 100 100
1-006 + V02 300 + 5 100 100
1-006 + V03 300 + 10 100 100
1-006 + W10 300 + 10 100 100
1-006 + X02 300 + 30 100 100
1-006 + X05 300 + 10 100 100
1-006 + Y01 300 + 20 100 100
1-006 + Z08 300 + 5 100 100
1-006 + Z12 300 + 20 100 100
1-006 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 37]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + S01 300 + 3 100 100
1-007 + U02 300 + 3 100 100
1-007 + V01 300 + 5 100 100
1-007 + V02 300 + 5 100 100
1-007 + V03 300 + 10 100 100
1-007 + W10 300 + 10 100 100
1-007 + X02 300 + 30 100 100
1-007 + X05 300 + 10 100 100
1-007 + Y01 300 + 20 100 100
1-007 + Z08 300 + 5 100 100
1-007 + Z12 300 + 20 100 100
1-007 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 38]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + S01 300 + 3 100 100
1-008 + U02 300 + 3 100 100
1-008 + V01 300 + 5 100 100
1-008 + V02 300 + 5 100 100
1-008 + V03 300 + 10 100 100
1-008 + W10 300 + 10 100 100
1-008 + X02 300 + 30 100 100
1-008 + X05 300 + 10 100 100
1-008 + Y01 300 + 20 100 100
1-008 + Z08 300 + 5 100 100
1-008 + Z12 300 + 20 100 100
1-008 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 39]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + S01 300 + 3 100 100
1-009 + U02 300 + 3 100 100
1-009 + V01 300 + 5 100 100
1-009 + V02 300 + 5 100 100
1-009 + V03 300 + 10 100 100
1-009 + W10 300 + 10 100 100
1-009 + X02 300 + 30 100 100
1-009 + X05 300 + 10 100 100
1-009 + Y01 300 + 20 100 100
1-009 + Z08 300 + 5 100 100
1-009 + Z12 300 + 20 100 100
1-009 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 40]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + S01 300 + 3 100 100
2-001 + U02 300 + 3 100 100
2-001 + V01 300 + 5 100 100
2-001 + V02 300 + 5 100 100
2-001 + V03 300 + 10 100 100
2-001 + W10 300 + 10 100 100
2-001 + X02 300 + 30 100 100
2-001 + X05 300 + 10 100 100
2-001 + Y01 300 + 20 100 100
2-001 + Z08 300 + 5 100 100
2-001 + Z12 300 + 20 100 100
2-001 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 41]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + S01 300 + 3 100 100
3-001 + U02 300 + 3 100 100
3-001 + V01 300 + 5 100 100
3-001 + V02 300 + 5 100 100
3-001 + V03 300 + 10 100 100
3-001 + W10 300 + 10 100 100
3-001 + X02 300 + 30 100 100
3-001 + X05 300 + 10 100 100
3-001 + Y01 300 + 20 100 100
3-001 + Z08 300 + 5 100 100
3-001 + Z12 300 + 20 100 100
3-001 + Z14 300 + 10 100 100
―――――――――――――――――――――――――――
[Test Example 2] Efficacy test against peach aphid larvae The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to Formulation Examples. The preparation was diluted with water containing a spreading agent to prepare a chemical solution having a predetermined concentration.
A moist filter paper was laid on a glass petri dish having an inner diameter of 3 cm, and cabbage leaves of the same diameter were placed thereon. The peach aphid larvae were born by releasing 5 adult females of the green peach aphid and placing them overnight. Immediately before spraying, female peach aphid was removed, and a chemical solution was sprayed uniformly (2.5 mg / cm ² ) using a spraying device. The number of larvae killed 6 days after the treatment was investigated, and the death rate and expected value were calculated using the calculation formula described in Test Example 1. In addition, the test was performed by 2 continuous systems.

Tables 42 to 53 show the results regarding the death rate of each chemical solution.
[Table 42]
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 500 100
1-002 500 100
1-003 500 100
1-004 500 100
1-005 500 100
1-006 500 100
1-007 500 93
1-008 500 88
1-009 500 100
2-001 500 100
3-001 500 96
N03 100 100
N08 100 100
P04 10 100
P07 30 100
P10 10 100
R01 5 100
R02 5 100
R03 10 100
R04 5 100
R05 10 100
R06 5 100
R07 5 100
R08 5 100
R09 30 100
Z01 5 100
Z04 5 100
Z07 5 100
―――――――――――――――――――――
[Table 43]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + N03 500 + 100 100 100
1-001 + N08 500 + 100 100 100
1-001 + P04 500 + 10 100 100
1-001 + P07 500 + 30 100 100
1-001 + P10 500 + 10 100 100
1-001 + R01 500 + 5 100 100
1-001 + R02 500 + 5 100 100
1-001 + R03 500 + 10 100 100
1-001 + R04 500 + 5 100 100
1-001 + R05 500 + 10 100 100
1-001 + R06 500 + 5 100 100
1-001 + R07 500 + 5 100 100
1-001 + R08 500 + 5 100 100
1-001 + R09 500 + 30 100 100
1-001 + Z01 500 + 20 100 100
1-001 + Z04 500 + 5 100 100
1-001 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 44]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + N03 500 + 100 100 100
1-002 + N08 500 + 100 100 100
1-002 + P04 500 + 10 100 100
1-001 + P04 500 + 30 100 100
1-002 + P10 500 + 10 100 100
1-002 + R01 500 + 5 100 100
1-002 + R02 500 + 5 100 100
1-002 + R03 500 + 10 100 100
1-002 + R04 500 + 5 100 100
1-002 + R05 500 + 10 100 100
1-002 + R06 500 + 5 100 100
1-002 + R07 500 + 5 100 100
1-002 + R08 500 + 5 100 100
1-002 + R09 500 + 30 100 100
1-002 + Z01 500 + 20 100 100
1-002 + Z04 500 + 5 100 100
1-002 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 45]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + N03 500 + 100 100 100
1-003 + N08 500 + 100 100 100
1-003 + P04 500 + 10 100 100
1-003 + P04 500 + 30 100 100
1-003 + P10 500 + 10 100 100
1-003 + R01 500 + 5 100 100
1-003 + R02 500 + 5 100 100
1-003 + R03 500 + 10 100 100
1-003 + R04 500 + 5 100 100
1-003 + R05 500 + 10 100 100
1-003 + R06 500 + 5 100 100
1-003 + R07 500 + 5 100 100
1-003 + R08 500 + 5 100 100
1-003 + R09 500 + 30 100 100
1-003 + Z01 500 + 20 100 100
1-003 + Z04 500 + 5 100 100
1-003 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 46]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + N03 500 + 100 100 100
1-004 + N08 500 + 100 100 100
1-004 + P04 500 + 10 100 100
1-004 + P04 500 + 30 100 100
1-004 + P10 500 + 10 100 100
1-004 + R01 500 + 5 100 100
1-004 + R02 500 + 5 100 100
1-004 + R03 500 + 10 100 100
1-004 + R04 500 + 5 100 100
1-004 + R05 500 + 10 100 100
1-004 + R06 500 + 5 100 100
1-004 + R07 500 + 5 100 100
1-004 + R08 500 + 5 100 100
1-004 + R09 500 + 30 100 100
1-004 + Z01 500 + 20 100 100
1-004 + Z04 500 + 5 100 100
1-004 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 47]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + N03 500 + 100 100 100
1-005 + N08 500 + 100 100 100
1-005 + P04 500 + 10 100 100
1-005 + P04 500 + 30 100 100
1-005 + P10 500 + 10 100 100
1-005 + R01 500 + 5 100 100
1-005 + R02 500 + 5 100 100
1-005 + R03 500 + 10 100 100
1-005 + R04 500 + 5 100 100
1-005 + R05 500 + 10 100 100
1-005 + R06 500 + 5 100 100
1-005 + R07 500 + 5 100 100
1-005 + R08 500 + 5 100 100
1-005 + R09 500 + 30 100 100
1-005 + Z01 500 + 20 100 100
1-005 + Z04 500 + 5 100 100
1-005 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 48]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + N03 500 + 100 100 100
1-006 + N08 500 + 100 100 100
1-006 + P04 500 + 10 100 100
1-006 + P04 500 + 30 100 100
1-006 + P10 500 + 10 100 100
1-006 + R01 500 + 5 100 100
1-006 + R02 500 + 5 100 100
1-006 + R03 500 + 10 100 100
1-006 + R04 500 + 5 100 100
1-006 + R05 500 + 10 100 100
1-006 + R06 500 + 5 100 100
1-006 + R07 500 + 5 100 100
1-006 + R08 500 + 5 100 100
1-006 + R09 500 + 30 100 100
1-006 + Z01 500 + 20 100 100
1-006 + Z04 500 + 5 100 100
1-006 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 49]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + N03 500 + 100 100 100
1-007 + N08 500 + 100 100 100
1-007 + P04 500 + 10 100 100
1-007 + P04 500 + 30 100 100
1-007 + P10 500 + 10 100 100
1-007 + R01 500 + 5 100 100
1-007 + R02 500 + 5 100 100
1-007 + R03 500 + 10 100 100
1-007 + R04 500 + 5 100 100
1-007 + R05 500 + 10 100 100
1-007 + R06 500 + 5 100 100
1-007 + R07 500 + 5 100 100
1-007 + R08 500 + 5 100 100
1-007 + R09 500 + 30 100 100
1-007 + Z01 500 + 20 100 100
1-007 + Z04 500 + 5 100 100
1-007 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 50]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + N03 500 + 100 100 100
1-008 + N08 500 + 100 100 100
1-008 + P04 500 + 10 100 100
1-008 + P04 500 + 30 100 100
1-008 + P10 500 + 10 100 100
1-008 + R01 500 + 5 100 100
1-008 + R02 500 + 5 100 100
1-008 + R03 500 + 10 100 100
1-008 + R04 500 + 5 100 100
1-008 + R05 500 + 10 100 100
1-008 + R06 500 + 5 100 100
1-008 + R07 500 + 5 100 100
1-008 + R08 500 + 5 100 100
1-008 + R09 500 + 30 100 100
1-008 + Z01 500 + 20 100 100
1-008 + Z04 500 + 5 100 100
1-008 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 51]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + N03 500 + 100 100 100
1-009 + N08 500 + 100 100 100
1-009 + P04 500 + 10 100 100
1-009 + P04 500 + 30 100 100
1-009 + P10 500 + 10 100 100
1-009 + R01 500 + 5 100 100
1-009 + R02 500 + 5 100 100
1-009 + R03 500 + 10 100 100
1-009 + R04 500 + 5 100 100
1-009 + R05 500 + 10 100 100
1-009 + R06 500 + 5 100 100
1-009 + R07 500 + 5 100 100
1-009 + R08 500 + 5 100 100
1-009 + R09 500 + 30 100 100
1-009 + Z01 500 + 20 100 100
1-009 + Z04 500 + 5 100 100
1-009 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 52]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + N03 500 + 100 100 100
2-001 + N08 500 + 100 100 100
2-001 + P04 500 + 10 100 100
2-001 + P07 500 + 30 100 100
2-001 + P10 500 + 10 100 100
2-001 + R01 500 + 5 100 100
2-001 + R02 500 + 5 100 100
2-001 + R03 500 + 10 100 100
2-001 + R04 500 + 5 100 100
2-001 + R05 500 + 10 100 100
2-001 + R06 500 + 5 100 100
2-001 + R07 500 + 5 100 100
2-001 + R08 500 + 5 100 100
2-001 + R09 500 + 30 100 100
2-001 + Z01 500 + 20 100 100
2-001 + Z04 500 + 5 100 100
2-001 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 53]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + N03 500 + 100 100 100
3-001 + N08 500 + 100 100 100
3-001 + P04 500 + 10 100 100
3-001 + P07 500 + 30 100 100
3-001 + P10 500 + 10 100 100
3-001 + R01 500 + 5 100 100
3-001 + R02 500 + 5 100 100
3-001 + R03 500 + 10 100 100
3-001 + R04 500 + 5 100 100
3-001 + R05 500 + 10 100 100
3-001 + R06 500 + 5 100 100
3-001 + R07 500 + 5 100 100
3-001 + R08 500 + 5 100 100
3-001 + R09 500 + 30 100 100
3-001 + Z01 500 + 20 100 100
3-001 + Z04 500 + 5 100 100
3-001 + Z08 500 + 10 100 100
―――――――――――――――――――――――――――
[Test Example 3] Efficacy test against nymph mite larvae Five adult nymph mites were released on a leaf disk (diameter 1 cm) prepared in advance with green beans and allowed to lay overnight in a thermostatic chamber at 25 degrees. The next day, after removing the female adult spider mite from the leaf disc, the leaf disc was maintained for 5 days to hatch the eggs.

  The day before the drug treatment day, tap water is filled into a styrene cup (lid diameter 7.5 cm x height 4 cm), and a lid with a hole in the center is put on it, and tap water is sucked onto the lid. So that the filter paper was laid. A leaf disk (3 cm in diameter) made of green beans was placed on the filter paper, and a leaf disk carrying the nymph mite larvae prepared in the above-described procedure was placed on the filter paper overnight to release the nymph mite larvae.

  The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to formulation examples. The preparation was diluted with water to prepare a chemical solution having a predetermined concentration. Using a spraying device, spraying solution was uniformly sprayed for each test container (2.5 ml / cup). The survey was conducted 6 days after spraying, and the death rate and expected value were calculated using the formulas described in Test Example 1. The test was conducted in a two ward system.

The results regarding the mortality of each chemical solution are shown in Tables 54 to 65 below.
[Table 54]
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 500 8
1-002 500 15
1-003 500 2
1-004 500 4
1-005 500 4
1-006 500 6
1-007 500 8
1-008 500 13
1-009 500 6
2-001 500 10
3-001 500 4
U01 5 100
W03 20 100
W05 20 100
Z06 30 100
Z13 20 100
―――――――――――――――――――――
[Table 55]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + U01 500 + 5 100 100
1-001 + W03 500 + 20 100 100
1-001 + W05 500 + 20 100 100
1-001 + Z06 500 + 30 100 100
1-001 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 56]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + U01 500 + 5 100 100
1-002 + W03 500 + 20 100 100
1-002 + W05 500 + 20 100 100
1-002 + Z06 500 + 30 100 100
1-002 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 57]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + U01 500 + 5 100 100
1-003 + W03 500 + 20 100 100
1-003 + W05 500 + 20 100 100
1-003 + Z06 500 + 30 100 100
1-003 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 58]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + U01 500 + 5 100 100
1-004 + W03 500 + 20 100 100
1-004 + W05 500 + 20 100 100
1-004 + Z06 500 + 30 100 100
1-004 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 59]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + U01 500 + 5 100 100
1-005 + W03 500 + 20 100 100
1-005 + W05 500 + 20 100 100
1-005 + Z06 500 + 30 100 100
1-005 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 60]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + U01 500 + 5 100 100
1-006 + W03 500 + 20 100 100
1-006 + W05 500 + 20 100 100
1-006 + Z06 500 + 30 100 100
1-006 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 61]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + U01 500 + 5 100 100
1-007 + W03 500 + 20 100 100
1-007 + W05 500 + 20 100 100
1-007 + Z06 500 + 30 100 100
1-007 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 62]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + U01 500 + 5 100 100
1-008 + W03 500 + 20 100 100
1-008 + W05 500 + 20 100 100
1-008 + Z06 500 + 30 100 100
1-008 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 63]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + U01 500 + 5 100 100
1-009 + W03 500 + 20 100 100
1-009 + W05 500 + 20 100 100
1-009 + Z06 500 + 30 100 100
1-009 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 64]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + U01 500 + 5 100 100
2-001 + W03 500 + 20 100 100
2-001 + W05 500 + 20 100 100
2-001 + Z06 500 + 30 100 100
2-001 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 65]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + U01 500 + 5 100 100
3-001 + W03 500 + 20 100 100
3-001 + W05 500 + 20 100 100
3-001 + Z06 500 + 30 100 100
3-001 + Z13 500 + 20 100 100
―――――――――――――――――――――――――――
[Test Example 4] Efficacy test against black moth The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared in accordance with Formulation Examples. The preparation was diluted with water containing a spreading agent to prepare a chemical solution having a predetermined concentration. Cabbage leaves were put into the chemical solution and immersed for 10 seconds. Next, one processed cabbage leaf was transferred to a 7 cm petri dish with filter paper and dried in air. After air drying, 7 golden moth larvae were released per petri dish. After releasing, the petri dish was housed in a constant temperature room at 25 ° C. The number of larvae killed 6 days after the treatment was investigated, and the death rate and expected value were calculated using the calculation formula described in Test Example 1. In addition, the test was performed by 2 continuous systems.

Mortality (%) = dead insects / test insects x 100
Tables 66 to 77 show the results regarding the death rate of each chemical solution.
[Table 66]
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 300 100
1-002 300 100
1-003 300 100
1-004 300 100
1-005 300 100
1-006 300 100
1-007 300 100
1-008 300 100
1-009 300 100
2-001 300 100
3-001 300 100
N12 100 100
P02 10 100
S02 1 100
T02 5 100
T03 10 100
V05 10 100
X04 10 100
―――――――――――――――――――――
[Table 67]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + N12 300 + 100 100 100
1-001 + P02 300 + 10 100 100
1-001 + S02 300 + 1 100 100
1-001 + T02 300 + 5 100 100
1-001 + T03 300 + 10 100 100
1-001 + V05 300 + 10 100 100
1-001 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 68]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + N12 300 + 100 100 100
1-002 + P02 300 + 10 100 100
1-002 + S02 300 + 1 100 100
1-002 + T02 300 + 5 100 100
1-002 + T03 300 + 10 100 100
1-002 + V05 300 + 10 100 100
1-002 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 69]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + N12 300 + 100 100 100
1-003 + P02 300 + 10 100 100
1-003 + S02 300 + 1 100 100
1-003 + T02 300 + 5 100 100
1-003 + T03 300 + 10 100 100
1-003 + V05 300 + 10 100 100
1-003 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 70]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + N12 300 + 100 100 100
1-004 + P02 300 + 10 100 100
1-004 + S02 300 + 1 100 100
1-004 + T02 300 + 5 100 100
1-004 + T03 300 + 10 100 100
1-004 + V05 300 + 10 100 100
1-004 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 71]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + N12 300 + 100 100 100
1-005 + P02 300 + 10 100 100
1-005 + S02 300 + 1 100 100
1-005 + T02 300 + 5 100 100
1-005 + T03 300 + 10 100 100
1-005 + V05 300 + 10 100 100
1-005 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 72]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + N12 300 + 100 100 100
1-006 + P02 300 + 10 100 100
1-006 + S02 300 + 1 100 100
1-006 + T02 300 + 5 100 100
1-006 + T03 300 + 10 100 100
1-006 + V05 300 + 10 100 100
1-006 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 73]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + N12 300 + 100 100 100
1-007 + P02 300 + 10 100 100
1-007 + S02 300 + 1 100 100
1-007 + T02 300 + 5 100 100
1-007 + T03 300 + 10 100 100
1-007 + V05 300 + 10 100 100
1-007 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 74]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + N12 300 + 100 100 100
1-008 + P02 300 + 10 100 100
1-008 + S02 300 + 1 100 100
1-008 + T02 300 + 5 100 100
1-008 + T03 300 + 10 100 100
1-008 + V05 300 + 10 100 100
1-008 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 75]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + N12 300 + 100 100 100
1-009 + P02 300 + 10 100 100
1-009 + S02 300 + 1 100 100
1-009 + T02 300 + 5 100 100
1-009 + T03 300 + 10 100 100
1-009 + V05 300 + 10 100 100
1-009 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 76]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + N12 300 + 100 100 100
2-001 + P02 300 + 10 100 100
2-001 + S02 300 + 1 100 100
2-001 + T02 300 + 5 100 100
2-001 + T03 300 + 10 100 100
2-001 + V05 300 + 10 100 100
2-001 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Table 77]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + N12 300 + 100 100 100
3-001 + P02 300 + 10 100 100
3-001 + S02 300 + 1 100 100
3-001 + T02 300 + 5 100 100
3-001 + T03 300 + 10 100 100
3-001 + V05 300 + 10 100 100
3-001 + X04 300 + 10 100 100
―――――――――――――――――――――――――――
[Test Example 5] Efficacy test against citrus red mite larvae 20 adult females of citrus red mite were released on a leaf disk (diameter 2 cm) prepared in advance with citrus leaves and allowed to lay eggs overnight in a constant temperature room at 25 degrees. The next day, after removing the adult mandarin mite from the leaf disc, the leaf disc was maintained for 6 days to hatch the eggs.

  The day before the drug treatment day, tap water is filled into a styrene cup (lid diameter 7.5 cm x height 4 cm), and a lid with a hole in the center is put on it, and tap water is sucked onto the lid. So that the filter paper was laid. Spread the cotton on the filter paper, place the leaf disk (3cm in diameter) made from mandarin leaves, and place the leaf disk with the citrus spider mite larvae prepared in the above procedure on it overnight to release the spider mite larvae. did.

  The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to formulation examples. The preparation was diluted with water to prepare a chemical solution having a predetermined concentration. Using a spraying device, spraying solution was uniformly sprayed for each test container (2.5 ml / cup). The survey was conducted 6 days after spraying, and the death rate and expected value were calculated using the formulas described in Test Example 1. The test was conducted in a two ward system.

The results regarding the mortality of each chemical solution are shown in Tables 78 to 89 [Table 78].
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 500 3
1-002 500 9
1-003 500 6
1-004 500 3
1-005 500 3
1-006 500 3
1-007 500 3
1-008 500 6
1-009 500 3
2-001 500 9
3-001 500 6
W05 10 100
Z05 10 100
―――――――――――――――――――――
[Table 79]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + W05 500 + 100 100 100
1-001 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 80]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + W05 500 + 100 100 100
1-002 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 81]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + W05 500 + 100 100 100
1-003 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 82]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + W05 500 + 100 100 100
1-004 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 83]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + W05 500 + 100 100 100
1-005 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 84]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + W05 500 + 100 100 100
1-006 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 85]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + W05 500 + 100 100 100
1-007 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 86]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + W05 500 + 100 100 100
1-008 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 87]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + W05 500 + 100 100 100
1-009 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 88]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + W05 500 + 100 100 100
2-001 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Table 89]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + W05 500 + 100 100 100
3-001 + Z05 500 + 10 100 100
―――――――――――――――――――――――――――
[Test Example 6] Efficacy test against tobacco whitefly larvae Fill a styrene cup (with a lid diameter of 7.5 cm and a height of 4 cm) with tap water. A filter paper was laid to absorb tap water. Cotton was spread on the filter paper, and a leaf disk (diameter 3 cm) made of green beans was placed on the filter paper. Here, 10 adult female whitefly insects were released, covered with lids to prevent escape, and laid overnight in a thermostatic chamber at 25 degrees. The next day, after removing the adult whitefly whitefly from the leaf disc, the leaf disc was maintained for 6 days to hatch the eggs.

  The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to formulation examples. The preparation was diluted with water to prepare a chemical solution having a predetermined concentration. Using a spraying device, spraying solution was uniformly sprayed for each test container (2.5 ml / cup). The survey was conducted 6 days after spraying, and the death rate and expected value were calculated using the formulas described in Test Example 1. The test was conducted in a two ward system.

The results regarding the mortality of each chemical solution are shown in Tables 90 to 101 [Table 90].
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 500 28
1-002 500 42
1-003 500 23
1-004 500 32
1-005 500 48
1-006 500 25
1-008 500 20
1-009 500 36
1-010 500 27
2-001 500 18
3-001 500 26
R01 20 100
W03 30 100
X01 10 100
X08 50 100
Z07 30 100
Z14 20 100
―――――――――――――――――――――
[Table 91]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + R01 500 + 20 100 100
1-001 + W03 500 + 30 100 100
1-001 + X01 500 + 10 100 100
1-001 + X08 500 + 50 100 100
1-001 + Z07 500 + 30 100 100
1-001 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 92]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + R01 500 + 20 100 100
1-002 + W03 500 + 30 100 100
1-002 + X01 500 + 10 100 100
1-002 + X08 500 + 50 100 100
1-002 + Z07 500 + 30 100 100
1-002 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 93]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + R01 500 + 20 100 100
1-003 + W03 500 + 30 100 100
1-003 + X01 500 + 10 100 100
1-003 + X08 500 + 50 100 100
1-003 + Z07 500 + 30 100 100
1-003 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 94]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + R01 500 + 20 100 100
1-004 + W03 500 + 30 100 100
1-004 + X01 500 + 10 100 100
1-004 + X08 500 + 50 100 100
1-004 + Z07 500 + 30 100 100
1-004 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 95]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + R01 500 + 20 100 100
1-005 + W03 500 + 30 100 100
1-005 + X01 500 + 10 100 100
1-005 + X08 500 + 50 100 100
1-005 + Z07 500 + 30 100 100
1-005 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 96]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + R01 500 + 20 100 100
1-006 + W03 500 + 30 100 100
1-006 + X01 500 + 10 100 100
1-006 + X08 500 + 50 100 100
1-006 + Z07 500 + 30 100 100
1-006 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 97]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + R01 500 + 20 100 100
1-007 + W03 500 + 30 100 100
1-007 + X01 500 + 10 100 100
1-007 + X08 500 + 50 100 100
1-007 + Z07 500 + 30 100 100
1-007 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 98]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + R01 500 + 20 100 100
1-008 + W03 500 + 30 100 100
1-008 + X01 500 + 10 100 100
1-008 + X08 500 + 50 100 100
1-008 + Z07 500 + 30 100 100
1-008 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 99]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + R01 500 + 20 100 100
1-009 + W03 500 + 30 100 100
1-009 + X01 500 + 10 100 100
1-009 + X08 500 + 50 100 100
1-009 + Z07 500 + 30 100 100
1-009 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 100]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + R01 500 + 20 100 100
2-001 + W03 500 + 30 100 100
2-001 + X01 500 + 10 100 100
2-001 + X08 500 + 50 100 100
2-001 + Z07 500 + 30 100 100
2-001 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Table 101]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + R01 500 + 20 100 100
3-001 + W03 500 + 30 100 100
3-001 + X01 500 + 10 100 100
3-001 + X08 500 + 50 100 100
3-001 + Z07 500 + 30 100 100
3-001 + Z14 500 + 20 100 100
―――――――――――――――――――――――――――
[Test Example 7] Efficacy test against leafhopper leaflets The compounds described in Tables 1 to 3 and the active ingredients described in Tables 4 to 29 were prepared according to Formulation Examples. The preparation was diluted with water containing a spreading agent to prepare a chemical solution having a predetermined concentration. Rice leaf sheath was put into the chemical solution and immersed for 10 seconds. After air drying, one treated rice leaf sheath was transferred per test tube. There, 7 larvae of the leafhopper were infested per test tube and covered with a sponge. After releasing, the test tube was placed in a constant temperature room at 25 ° C. The number of larvae killed 6 days after the treatment was investigated, and the death rate and expected value were calculated using the calculation formula described in Test Example 1. In addition, the test was performed by 2 continuous systems.

Tables 102 to 113 show the results regarding the death rate of each chemical solution.
[Table 102]
―――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%)
―――――――――――――――――――――
1-001 300 100
1-002 300 100
1-003 300 100
1-004 300 100
1-005 300 100
1-006 300 100
1-007 300 100
1-008 300 100
1-009 300 100
2-001 300 100
3-001 300 100
R10 10 100
T01 30 100
V01 20 100
V02 20 100
W03 30 100
W04 20 100
Z14 20 100
―――――――――――――――――――――
[Table 103]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-001 + R10 300 + 10 100 100
1-001 + T01 300 + 30 100 100
1-001 + V01 300 + 20 100 100
1-001 + V02 300 + 20 100 100
1-001 + W03 300 + 30 100 100
1-001 + W04 300 + 20 100 100
1-001 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 104]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-002 + R10 300 + 10 100 100
1-002 + T01 300 + 30 100 100
1-002 + V01 300 + 20 100 100
1-002 + V02 300 + 20 100 100
1-002 + W03 300 + 30 100 100
1-002 + W04 300 + 20 100 100
1-002 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 105]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-003 + R10 300 + 10 100 100
1-003 + T01 300 + 30 100 100
1-003 + V01 300 + 20 100 100
1-003 + V02 300 + 20 100 100
1-003 + W03 300 + 30 100 100
1-003 + W04 300 + 20 100 100
1-003 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 106]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-004 + R10 300 + 10 100 100
1-004 + T01 300 + 30 100 100
1-004 + V01 300 + 20 100 100
1-004 + V02 300 + 20 100 100
1-004 + W03 300 + 30 100 100
1-004 + W04 300 + 20 100 100
1-004 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 107]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-005 + R10 300 + 10 100 100
1-005 + T01 300 + 30 100 100
1-005 + V01 300 + 20 100 100
1-005 + V02 300 + 20 100 100
1-005 + W03 300 + 30 100 100
1-005 + W04 300 + 20 100 100
1-005 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 108]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-006 + R10 300 + 10 100 100
1-006 + T01 300 + 30 100 100
1-006 + V01 300 + 20 100 100
1-006 + V02 300 + 20 100 100
1-006 + W03 300 + 30 100 100
1-006 + W04 300 + 20 100 100
1-006 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 109]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-007 + R10 300 + 10 100 100
1-007 + T01 300 + 30 100 100
1-007 + V01 300 + 20 100 100
1-007 + V02 300 + 20 100 100
1-007 + W03 300 + 30 100 100
1-007 + W04 300 + 20 100 100
1-007 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 110]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-008 + R10 300 + 10 100 100
1-008 + T01 300 + 30 100 100
1-008 + V01 300 + 20 100 100
1-008 + V02 300 + 20 100 100
1-008 + W03 300 + 30 100 100
1-008 + W04 300 + 20 100 100
1-008 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 111]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
1-009 + R10 300 + 10 100 100
1-009 + T01 300 + 30 100 100
1-009 + V01 300 + 20 100 100
1-009 + V02 300 + 20 100 100
1-009 + W03 300 + 30 100 100
1-009 + W04 300 + 20 100 100
1-009 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 112]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
2-001 + R10 300 + 10 100 100
2-001 + T01 300 + 30 100 100
2-001 + V01 300 + 20 100 100
2-001 + V02 300 + 20 100 100
2-001 + W03 300 + 30 100 100
2-001 + W04 300 + 20 100 100
2-001 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――
[Table 113]
―――――――――――――――――――――――――――
Compound number Concentration (ppm) Mortality (%) Expected value ―――――――――――――――――――――――――――
3-001 + R10 300 + 10 100 100
3-001 + T01 300 + 30 100 100
3-001 + V01 300 + 20 100 100
3-001 + V02 300 + 20 100 100
3-001 + W03 300 + 30 100 100
3-001 + W04 300 + 20 100 100
3-001 + Z14 300 + 20 100 100
―――――――――――――――――――――――――――

  The composition of the present invention and the method of the present invention can be used for controlling various pests.

Claims (7)

An insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal composition comprising a synergistically effective amount of at least two active compounds,
1) One or two active compounds I are of the formula (1):

[Wherein Q represents a ring represented by either Q1 or Q3;

A ^1a represents C ₁ -C ₆ alkyl,
A ⁴ represents a nitrogen atom or C (R ⁴ ),
A ⁵ represents a nitrogen atom or C (R ⁵ ),
R ¹ represents C ₁ -C ₆ alkyl;
R ³ represents halo (C ₁ -C ₆ ) alkyl, halo (C ₁ -C ₆ ) alkylthio, halo (C ₁ -C ₆ ) alkylsulfinyl or halo (C ₁ -C ₆ ) alkylsulfonyl;
R ⁴ represents a hydrogen atom,
R ⁵ represents a hydrogen atom,
Y2, Y3 and Y4 each independently represent a hydrogen atom, a halogen atom, a halo _(C 1 _{~C 6)} alkyl or cyano,
n represents an integer of 0, 1 or 2. A fused heterocyclic compound represented by the formula:
2) One or more active compounds II are the following active ingredient groups BI to B-XXVI:
Active ingredient group BI: Metalaxyl-M and hymexazole.
Active ingredient group B-II: Benomyl, thiophanate-methyl, dietofencarb, ethaboxam, zoxamide, penciclone and fluopicolide.
Active ingredient group B-III: benzovindiflupyr, bixafen, boscalid, fluindapir, fluopyram, flutolanil, fluxapyroxad, furametopil, isoflucipram, impylfluxam, isofetamide, isopyrazam, mepronil, penflufen, pentiopyrad, sedaxane, Tifluzamide, azoxystrobin, cumoxystrobin, dimoxystrobin, enestrobine, enoxastrobin, famoxadone, phenamidon, phenaminestrobin, fluphenoxystrobin, fluoxastrobin, cresoxime-methyl, mandestrobin, metomi Nostrobin, orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, pyribencarb methyl, pyrimino Thrombin, trichloride pyridinium benthiavalicarb, trifloxystrobin, amisulbrom, cyazofamid, fluazinam, Fen pico alkylcarboxamide, Ametokutorajin, Piji full methemoglobin und Pirajifurumido.
Active ingredient group B-IV: mepanipyrim and kasugamycin.
Active ingredient group BV: quinoxyphene and fludioxonil.
Active ingredient group B-VI: iprodione and procymidone.
Active ingredient group B-VII: Torquelophos-methyl and Bacillus subtilis.
Active ingredient group B-VIII: bromconazole, cyproconazole, difenoconazole, diniconazole-M, epoxiconazole, phenarimol, fenbuconazole, fluquinconazole, hexaconazole, imazalyl, imibenconazole, ipconazole, metconazole, microbutanyl , Penconazole, prochloraz, propiconazole, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triflumizole, fenpropidin, fenhexamide, fenpyrazamine, ipfentrifluconazole and mefentrifluconazole.
Active ingredient group B-IX: Validamycin, polyoxin, polyoxin-D, benchavaricarb-isopropyl, dimethomorph, iprovaricarb and mandipropamide.
Active ingredient group BX: fusaride, tricyclazole, carpropamide and diclocimet.
Active ingredient group B-XI: acibenzoral-S-methyl, probenazole, isotianil, diclobenchazox and thiazinyl.
Active ingredient group B-XII: Bordeaux liquid, basic copper carbonate, cupric hydroxide, copper naphthenate, copper oleate, basic copper chloride, copper sulfate, basic copper sulfate, oxyquinoline copper, lime sulfur mixture, Sulfur, mancozeb, mannebu, polycarbamate, propineb, captan, phorpet, chlorothalonil, iminoctadine-albesylate and iminoctadine acetate.
Active ingredient group B-XIII: aminopyriphene, cyflufenamide, simoxanyl, fursulfamide, fluthianyl, fosetyl-aluminum, metraphenone, oxathiapiproline, pyriophenone, picalbutradox, dipimethitrone, quinofumerin, lipopeptide, phosphorous acid, BCF- 082 (test name), NF-180 (test name), S-2399 (test name), AKD-5195 (test name) and S-2190 (test name).
Active ingredient group B-XIV: acephate, kazusafos, chlorpyrifos, diazinon, dichlorvos, dimethoate, EPN, malathion, methamidophos, parathion-methyl, phentoate, folate, phosmet, oxime, profenofos and terbufos.
Active ingredient group B-XV: aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, mesomil, pirimicarb and thiodicarb.
Active ingredient group B-XVI: Acrinathrin, bifenthrin, cyfluthrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, permethrin, tefluthrin, lambda-cyhalothrin and tau-fulvalinate.
Active ingredient group B-XVII: bensultap, cartap and thiocyclam.
Active ingredient group B-XVIII: Acetamiprid, clothianidin, dinotefuran, flupirmine, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, sulfoxafurol, flupiradiflon, triflumezopyrim and dichloromezothiaz.
Active ingredient group B-XIX: Spinetoram and spinosad Active ingredient group B-XX: Ethiprole, fipronil and brofuranilide.
Active ingredient group B-XXI: Abamectin, emamectin benzoate, repimectin and milbemectin.
Active ingredient group B-XXII: chlorantraniliprole, cyantraniliprole, fulvendiamide, cyclaniliprol, tetranyriprole and cyhalodiamide.
Active ingredient group B-XXIII: diafenthiuron, fenpyroximate, pyridaben, tolfenpyrad, sienopyrafen, cyflumethofene, piflumide, hydramethylnon, acequinosyl and chlorfenapyr.
Active ingredient group B-XXIV: benzpyrimoxane, pyriproxyfen, methoxyphenozide, diflubenzuron, flufenoxuron, lufenuron, nobarulone, teflubenzuron, buprofezin, hexathiazox and etoxazole.
Active ingredient group B-XXV: Bacillus thuringiensis and Bacillus sphaericus.
Active ingredient group B-XXVI: Acinonapyr, Pymetrozine, Pyrifluquinazone, Afidopyropene, Flonicamid, Spirodiclofen, Spiromesifene, Spiropidione, Spirotetramat, Indoxacarb, Metaflumizone, Siromazine, Azadilactin, Pyridalil, Bifenazate, Floxamethamide, Aldehyde, ME-5382 (test name), NA-89 (test name), NNI-1501 (test name), BAI-1602 (test name), DKN-2601 (test name) and DAI-1601 (test name).
Said insecticidal, acaricidal, nematicidal, molluscicidal, bactericidal or bactericidal composition which is a compound selected from. Q represents a ring represented by Q1,
A ⁴ represents C (R ⁴ ),
A ⁵ represents a nitrogen atom,
R ³ represents halo (C ₁ -C ₆ ) alkyl or halo (C ₁ -C ₆ ) alkylsulfinyl,
Y2 and Y3 represent each independently a hydrogen atom, a halogen atom or a halo _(C 1 _{~C 6)} alkyl,
Y4 represents a hydrogen atom, a halogen atom or cyano,
The insecticidal, acaricidal, nematicidal, bactericidal or bactericidal composition according to claim 1, wherein n represents an integer of 2.   Acetamiprid, clothianidin, imidacloprid, thiamethoxam, suloxafurol, spinetoram, emamectin benzoate, chlorantraniliprole, cyantraniliprole, fulvendiamide, pyridaben, sienopyraphene, chlorfenapyr, bacillus thuringiensis, pymetrozine, flonicamido 4. An insecticidal, acaricidal, nematicidal, bactericidal or bactericidal composition according to claim 1 or 2, comprising an active compound II selected from, pyridalyl, bifenazate and fluxamethamide.   Pests or diseases caused by treating one or two active compounds I according to claim 1 and one or more active compounds II according to claim 1 simultaneously or close in time Control method.   Claim 4 by treating one or two active compounds I according to claim 2 and one or more active compounds II according to claim 3 simultaneously or close in time. The pest or disease control method described.   Claims by treating seeds with one or two active compounds I according to claim 1 and one or more active compounds II according to claim 1 simultaneously or close in time Item 5. A method for controlling a pest or disease according to Item 4.   Claim by treating one or two active compounds I according to claim 2 and one or more active compounds II according to claim 3 to the seed simultaneously or in close proximity in time Item 7. A pest or disease control method according to Item 6.