WO2017073733A1

WO2017073733A1 - Pest control composition and use thereof

Info

Publication number: WO2017073733A1
Application number: PCT/JP2016/082078
Authority: WO
Inventors: 慎哉西村
Original assignee: 住友化学株式会社
Priority date: 2015-10-30
Filing date: 2016-10-28
Publication date: 2017-05-04

Abstract

The present invention provides a pest control composition having an excellent controlling effect on pests, containing: a compound represented by the formula (I) [in the formula, each reference symbols represents definitions described in the specification] or a nitrogen oxide composition thereof; and at least one composition selected from the group consisting of group (a) and group (b).

Description

Pest control composition and use thereof

This patent application includes priority under the Paris Convention based on Japanese Patent Application No. 2015-2114016 (filed on October 30, 2015) and Japanese Patent Application No. 2016-144442 (filed on July 22, 2016) and All of which are incorporated herein by reference in their entirety.

The present invention relates to a pest control composition and a pest control method.

Conventionally, many compounds are known as active ingredients of pest control compositions (see, for example, Non-Patent Document 1).

An object of the present invention is to provide a pest control composition having an excellent control effect against pests.

As a result of studying to find a pest control composition having an excellent control effect against pests, the present inventor has found that the compound represented by the following formula (I) or its N oxide compound, the following group (a) and the following group: It has been found that a composition containing one or more compounds selected from the group consisting of (b) has an excellent control effect against pests.

The present invention is as follows.
[1]
A compound represented by the following formula (I) or an N oxide compound thereof;
A pest control composition comprising one or more compounds selected from the group consisting of the following group (a) and the following group (b).
Formula (I):

[Where:
R ¹ is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, one or more halogen atoms (C1-C5 alkoxy), a C2-C5 alkyl group, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, having one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, having one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R ² represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R ³ each independently has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, and one or more substituents selected from group D. Or a phenyl group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , NR ¹¹ C (O) R ¹³ , NR ²⁴ NR ¹¹ C (O) R ¹³ , NR ¹¹ C (O) OR ¹⁴ , NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ¹¹ R ¹² , a cyano group, a nitro group, or a halogen atom,
R ⁶ is each independently a C1-C6 alkyl group optionally having one or more halogen atoms, OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , cyano Represents a group, a nitro group, or a halogen atom,
R ¹¹ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²⁴ , and R ²⁵ are each independently a hydrogen atom or a C1-C6 chain hydrocarbon optionally having one or more halogen atoms Represents a group,
R ¹² represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O) ₂ represents R ²³ ,
R ²³ represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, or a phenyl group which may have one or more substituents selected from group D;
R ^11a and R ^12a are taken together with the nitrogen atom to which they are attached to form a 3-7-membered non-aromatic heterocyclic group (the 3-7-membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R ¹³ represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R ¹⁴ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. The optionally substituted (C3-C6 cycloalkyl) C1-C3 alkyl group or the phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D; You may do it. },
R ¹⁵ and R ¹⁶ each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R ⁶ may be the same or different, and q is 2 or 3 In this case, the plurality of R ³ may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group which may have one or more halogen atoms, a C1-C6 alkylsulfanyl group which may have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may have one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group which may have one or more halogen atoms, hydroxy group, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a sulfanyl group, or a C1-C6 which may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR ²¹ , NR ^A group consisting of ²¹ R ²² , C (O) R ²¹ , OC (O) R ²¹ , C (O) OR ²¹ , a cyano group, a nitro group, and a halogen atom. {R ²¹ and R ²² each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group and a nitro group.
Group F: C1-C6 alkoxy group optionally having one or more halogen atoms, NHR ²¹ , NR ²¹ R ²² , cyano group, phenyl optionally having one or more substituents selected from Group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group A group consisting of a 3-7-membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of an optionally substituted C3-C6 alkenyloxy group, an optionally substituted C3-C6 alkynyloxy group, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]
Group (a):
A group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroup a-1:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupiradifurone, sulfoxafurol, triflumezopyrim, dichloromesothiaz and the following formula

The group which consists of a compound shown by these.
Subgroup a-2:
Acrinatrin, Aleslin, Bifenthrin, Kappabifenthrin, Bioarethrin, Bioresmethrin, Cycloproton, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, Gamma Cyhalothrin, Lambdacyhalothrin, Cypermethrin, Alpha Cypermethrin, Betacypermethrin, Theta Permethrin, zeta-cypermethrin, sigma-permethrin, ciphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, fluvinate, taufulvalinate, halfenprox, hepta Flutrin, imiprothrin, cadreslin, meperfluthrin, monfluorotrin, permethrin, phenothrin Prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, kappa Te full Trinh, tetramethrin, tetramethyl full Trinh, tralomethrin, transfluthrin, Benfurutorin, full Fen flufenprox, flumethrin, furamethrin, metofluthrin, the group consisting of profluthrin and dimefluthrin.
Subgroup a-3:
A group consisting of etiprol, fipronil, flufiprolol, afoxolanel, fluralanel, brofuranilide and floxamethamide.
Subgroup a-4:
A group consisting of chlorantraniliprole, cyantranylprolol, cyclaniliprol, fulvendiamide, tetraniprolol and cyhalodiamide.
Subgroup a-5:
Alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiophene carb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, metolcarb, oxamyl, pyrimicarb, dioxycarb, propoxyl Group consisting of thiophanox, triazamate, trimetacarb, XMC and xylylcarb.
Subgroup a-6:
A group consisting of abamectin, fluenesulfone, thioxazaphene and fluazaindolizine.
Subgroup a-7:
Mycorrhizal fungi, Arthrobotris dacteroides, Bacillus thuringiensis, Bacillus films, Bacillus megaterium, Bacillus amyloliquefaciens, Hilstera rosiliensis, Hilstera minnesotensis, Monacrosporium fimatopagum, Pasteurian nisawae , Pasteuria penetrans, Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
Group (b):
A group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
Subgroup b-1:
Azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, dinicoazole, diniconazole M, epoxiconazole, etaconazole, phenalimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriazole, hexaconazole, imazalil, Imibenconazole, ipconazole, metconazole, microbutanyl, nuarimol, oxpoconazole, oxpoconazole fumarate, pefazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole, cimeconazole, tebuconazole, tetrabuconazole Conazole, triadimephone, triadimenol, triflumizole, trifolin and tritico A group consisting of nasol.
Subgroup b-2:
Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, fluphenoxystrobin, floxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, A group consisting of orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, cyazofamide and amisulbrom.
Subgroup b-3:
A group consisting of benalaxyl, benalaxyl M, furaxyl, metalaxyl, metalaxyl M, oxadixyl and oflase.
Subgroup b-4:
Benodanyl, benzobindiflupyr, bixaphene, boscalid, carboxin, fenfram, fluopyram, flutolanil, fluxapyroxad, furametopyr, isophetamide, isopyrazam, mepronil, oxycarboxyl, pentiopyrad, penflufen, cedaxane, tifluzamide, pyradiflumide Phen, 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide, 3-difluoromethyl-1-methyl-N-[(3R) -1 , 1,3-Trimethylindan-4-yl] pyrazole-4-carboxamide, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4 -Carboxa 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide and N-cyclopropyl-3- (difluoro A group consisting of (methyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide.
Subgroup b-5:
The group consisting of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide and ethaboxam.
Subgroup b-6:
A group consisting of felbam, manzeb, manneb, methyle, propineb, thiuram, dineb, ziram, captan, captahol, holpet, chlorothalonil, tolylfluanid, guazatine, iminotadine, anilazine, dithianone, quinomethionate and fluorimide.
Subgroup b-7:
A group consisting of dimethomorph, flumorph, pyrimorph, bench avaricarb, bench avaricarb isopropyl, iprovaricarb, varifenalate and mandipropamide.
Subgroup b-8:
A group consisting of fenpiclonyl, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.
Subgroup b-9:
The group consisting of toluclophosmethyl, oxathiapiproline, picalbutrazox, fluopicolide and silthiofam.
[2]
A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) The pesticidal composition according to [1], wherein the ratio of is 100: 1 to 1: 100 by weight.
[3]
A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) The pesticidal composition according to [1], wherein the weight ratio is 10: 1 to 1:10 by weight.
[4]
A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pesticidal composition according to [1], wherein the weight ratio is 10,000: 1 to 1: 100 by weight.
[5]
A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pest control composition according to [1], wherein the weight ratio is 1000: 1 to 1:10 by weight.
[6]
A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to a pest or a habitat of the pest.
[7]
A method for controlling pests, comprising a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to a plant or soil for cultivating the plant.
[8]
A method for controlling pests, which comprises a step of applying an effective amount of the pest control composition according to any one of [1] to [5] to seeds or bulbs.
[9]
[1] A seed or bulb having an effective amount of the pesticidal composition according to any one of [1] to [5].

According to the present invention, pests can be controlled.

The pest control composition of the present invention (hereinafter referred to as the present composition) comprises a compound represented by the formula (I) or an N oxide compound thereof (hereinafter referred to as a compound represented by the formula (I) and an N oxide thereof. The compound is referred to as the present bipyridine compound) and one or more compounds selected from the group consisting of the group (a) and the group (b) (hereinafter referred to as the present compound).

Examples of substituents used in the description of the present specification will be described below.
“It may have one or more halogen atoms” means that when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
In this specification, the expression “CX-CY” means that the number of carbon atoms is X to Y. For example, the notation “C1-C6” means 1 to 6 carbon atoms.

A halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The “chain hydrocarbon group” represents an alkyl group, an alkenyl group, and an alkynyl group.
Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group are mentioned.
Examples of the “alkenyl group” include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group heptenyl group, octenyl group, nonenyl Group, and decenyl group.
Examples of the “alkynyl group” include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 4-pentynyl group, 5-hexynyl group, heptynyl group, octynyl group, nonynyl group, and decynyl group.
The “C2-C10 haloalkyl group” represents a group in which a hydrogen atom of a C2-C10 alkyl group is substituted with a halogen atom, and examples thereof include a chloroethyl group, a 2,2,2-trifluoroethyl group, 2-bromo-1 1,2,2,2-tetrafluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, perfluorohexyl group and perfluorodecyl group Can be mentioned.
The “C3-C10 haloalkenyl group” represents a group in which one or more hydrogen atoms of the C3-C10 alkenyl group are substituted with a halogen atom, and examples thereof include a C3-C10 fluoroalkenyl group. Examples of the “C3-C10 haloalkenyl group” include a 3,3,3-trifluoro-1-propenyl group and a 1-trifluoro-3-butenyl group.
The “C3-C10 haloalkynyl group” represents a group in which one or more hydrogen atoms of the C3-C10 alkynyl group are substituted with a halogen atom, and examples thereof include a C3-C10 fluoroalkynyl group. Examples of the “C3-C10 haloalkynyl group” include a 3,3,3-trifluoro-1-propynyl group.
The “C1-C6 alkyl group optionally having one or more halogen atoms” represents, for example, a group in which one or more hydrogen atoms of the C1-C6 alkyl group are substituted with a halogen atom. , 2,2-trifluoroethyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,4,4,4-hexafluoropropyl group.
The “C1-C6 chain hydrocarbon group having one or more halogen atoms” represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C2-C6 alkynyl group having one or more halogen atoms. The “C1-C6 alkyl group having one or more halogen atoms” refers to the “C1-C6 alkyl group optionally having one or more halogen atoms” and the “C2-C10 having one or more halogen atoms”. It is included in the definition of “chain hydrocarbon group”. “C2-C6 alkenyl group having one or more halogen atoms” and “C2-C6 alkynyl group having one or more halogen atoms” mean the above “C2-C10 chain hydrocarbon group having one or more halogen atoms”. Included in the definition of

Examples of the “cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

The “alkoxy group” represents a monovalent group in which the alkyl group is bonded to an oxygen atom. Examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n- Examples include butoxy, t-butoxy, s-butoxy, and 3-methylbutoxy.

“3-7-membered non-aromatic heterocyclic group” means an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine Ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, or 1,4-thiazepane ring Examples of the 3-7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from group E include the following groups.

Examples of the N oxide compound include a compound represented by the formula (Id), a compound represented by the formula (Ie), and a compound represented by the formula (If).

[Wherein the symbols have the same meaning as described above. ]

[Wherein the symbols have the same meaning as described above. ]

[Wherein the symbols have the same meaning as described above. ]

"Phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may have one or more substituents selected from group D}" includes, for example, a benzyl group, 2-fluorobenzyl Group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, 2- [4- (trifluoromethyl) phenyl] ethyl group.
“(C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms” refers to a group in which (C1-C5 alkoxy) and / or (C2-C5 alkyl) has one or more halogen atoms, For example, 2,2-difluoro-3- (2,2,2-trichloroethoxy) propyl group, 2- (2,2,2-trichloroethoxy) ethyl group, 1,1,2-trifluoro-2- ( Trifluoromethoxy) ethyl group, 2,2-difluoro-3- (2,2,2-trifluoroethoxy) propyl group, 2- (2,2,2-trifluoroethoxy) ethyl group, 2,2-difluoro An example is a -3-methoxypropyl group.
“(C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms” is a group in which (C1-C5 alkylsulfanyl) and / or (C2-C5 alkyl) has one or more halogen atoms. For example, a 2,2-difluoro-2- (trifluoromethylthio) ethyl group.
“(C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfinyl) and / or (C2-C5 alkyl) has one or more halogen atoms. For example, 2,2-difluoro-2- (trifluoromethanesulfinyl) ethyl group can be mentioned.
“(C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkylsulfonyl) and / or (C2-C5 alkyl) has one or more halogen atoms. Examples thereof include 2,2-difluoro-2- (trifluoromethanesulfonyl) ethyl group.

“(C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G” means that (C3-C7 cycloalkyl) and / or (C1-C3 alkyl) is one or more groups Represents a group having one or more substituents selected from G, for example, (2,2-difluorocyclopropyl) methyl group, [1- (trifluoromethyl) cyclopropyl] methyl group, [2- (trifluoromethyl) ) Cyclopropyl] methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and 2-cyclopropyl-3,3,3-trifluoropropyl group.
“C3-C7 cycloalkyl group having one or more substituents selected from group G” includes, for example, a 2,2-difluorocyclopropyl group, a 1- (2,2,2-trifluoroethyl) cyclopropyl group And 4- (trifluoromethyl) cyclohexyl group.
“5- or 6-membered aromatic heterocyclic group” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, and the 5-membered aromatic heterocyclic group is a pyrrolyl group, a furyl group, a thienyl group, or a pyrazolyl group. Represents a group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. To express.
“5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms” means pyrrolyl group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group, and tetrazolyl group Represents.

An alkylsulfanyl group, an alkylsulfinyl group, and an alkylsulfonyl group represent an S (O) z group having an alkyl group.
For example, examples of the alkylsulfanyl group in which z is 0 include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.
For example, examples of the alkylsulfinyl group in which z is 1 include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, and an isopropylsulfinyl group.
For example, examples of the alkylsulfonyl group in which z is 2 include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

Examples of the bipyridine compound include the following compounds.

In the present bipyridine compound, a compound wherein R ² is a C1-C6 alkyl group optionally having one or more halogen atoms;
In the bipyridine compound, a compound wherein R ² is a C1-C6 alkyl group;
In the bipyridine compound, a compound wherein R ² is an ethyl group;

In the present bipyridine compound, q is 0, 1, or 2, and each R ³ is independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B , One 5-membered aromatic heterocyclic group selected from group Q (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a compound that is a halogen atom;
Group Q:

{Drawing R ²⁶ represents one or more halogen atoms which may have a C1-C6 alkyl group. }

In the bipyridine compound, R ¹ is a C2-C10 haloalkyl group, or one or more with a halogen atom (C1-C5 alkoxy) C2-C5 alkyl group,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B -C6 alkenyl group, one 5-membered aromatic heterocyclic group selected from group Q (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), ^{^{^{OR 12, NR 11 R 12,}}} NR 11a R 12a, NR 24 NR 11 R 12, NR 11 C (O) R 13, NR 24 NR 11 C (O) R 13, NR 11 C (O) OR 14, NR ²⁴ NR ¹¹ C (O) OR ¹⁴ , NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , NR ²⁴ NR ¹¹ C (O) NR ¹⁵ R ¹⁶ , N = CHNR ¹⁵ R ¹⁶ , N = S (O) _x R ¹⁵ R ¹⁶ , S (O) _y R ¹⁵ , C (O) OR ¹⁷ , C (O) NR ¹¹ R ¹² , a cyano group, a nitro group, or a halogen atom,
a compound wherein p is 0, 1, or 2;

In the bipyridine compound, R ¹ is a C2-C10 haloalkyl group, or one or more with a halogen atom (C1-C5 alkoxy) C2-C5 alkyl group,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B A -C6 alkenyl group, a 5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D); OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a halogen atom,
p is 0, 1, or 2;
A compound in which R ⁶ is each independently OR ¹⁸ , NR ¹⁸ R ¹⁹ , C (O) OR ²⁵ , OC (O) R ²⁰ , a cyano group, a nitro group, or a halogen atom;

In the present bipyridine compound, R ¹ is a C2-C6 alkyl group having 2 or more fluorine atoms, or a (C1-C5 alkoxy) C2-C5 alkyl group having 1 or more fluorine atoms,
R ² is a C1-C6 alkyl group, q is 0, 1, or 2,
R ³ each independently has a C1-C6 alkyl group optionally having one or more substituents selected from group B, and may have one or more substituents selected from group B A -C6 alkenyl group, a 5-membered aromatic heterocyclic group containing 1 to 4 nitrogen atoms (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D); OR ¹² , NR ¹¹ R ¹² , NR ^11a R ^12a , NR ²⁴ NR ¹¹ R ¹² , or a halogen atom,
a compound in which p is 0, 1, or 2 and each R ⁶ is independently a cyano group or a halogen atom;

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having 4 or more fluorine atoms, or a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group,
R ² is an ethyl group,
q is 0, 1, or 2;
R ³ each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkenyl group optionally having one or more halogen atoms, one or more halogen atoms A triazole group optionally having NR ¹¹ R ¹² , or a halogen atom,
A compound in which R ¹¹ and R ¹² are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and p is 0;

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having 4 or more fluorine atoms,
R ² is an ethyl group, q is 0 or 1,
R ³ each independently represents a C1-C6 alkyl group having one or more halogen atoms, an 1,2,4-triazol-1-yl group optionally having one or more halogen atoms, NR ¹¹ R ¹² or a halogen atom,
R ¹¹ and R ¹² are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms;
A compound wherein p is 0.

In the present bipyridine compound, R ¹ is a C2-C10 haloalkyl group or a C3-C7 cycloalkyl group having one or more substituents selected from Group G;
R ² is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ³ each independently has a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ C (O) R ¹³ , or a halogen atom,
R ¹¹ , R ¹² , R ¹³ and R ²⁴ are a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
R ⁶ is a halogen atom,
n is 2,
q is 0, 1 or 2;
A compound wherein p is 0 or 1.

In the present bipyridine compound, R ¹ is a C2-C6 haloalkyl group or a C5-C7 cycloalkyl group having one or more halogen atoms,
R ² is a C1-C3 alkyl group,
Each R ³ is independently a 5- or 6-membered aromatic heterocyclic group, NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ C (O) R ¹³ , or a halogen atom;
R ¹¹ , R ¹² , R ¹³ and R ²⁴ are a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms,
R ⁶ is a halogen atom,
n is 2,
q is 0, 1 or 2;
A compound wherein p is 0 or 1.

In the present bipyridine compound, R ¹ is a C2-C6 fluoroalkyl group or a C5-C7 cycloalkyl group having one or more fluorine atoms,
R ² is a C1-C3 alkyl group,
R ³ is each independently a 5-membered heterocyclic group containing 1 to 4 nitrogen atoms, NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ C (O) R ¹³ , or a halogen atom Yes,
R ^11, R ^12, R ¹³ and R ²⁴ is hydrogen atom or a C1-C3 alkyl group,
R ⁶ is a chlorine atom,
n is 2,
q is 0, 1 or 2;
A compound wherein p is 0 or 1.

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having 2 or more fluorine atoms, or a cyclohexyl group having 1 or more fluorine atoms,
R ² is an ethyl group,
R ³ each independently has a 1,2,4-triazol-1-yl group optionally having one or more halogen atoms, NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ C (O) R ¹³ , or a halogen atom,
R ¹¹ , R ¹² , R ¹³ and R ²⁴ are a hydrogen atom or a methyl group,
R ⁶ is a chlorine atom,
n is 2,
q is 0, 1 or 2;
A compound wherein p is 0 or 1.

In the present bipyridine compound, R ¹ is a C3-C5 alkyl group having two or more fluorine atoms, or a 4,4-difluorocyclohexyl group,
R ² is an ethyl group,
Each R ³ independently represents a 1,2,4-triazol-1-yl group, NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ R ¹² , NR ²⁴ NR ¹¹ C (O) R ¹³ , a chlorine atom or a bromine atom; And
R ¹¹ , R ¹² and R ²⁴ are a hydrogen atom or a methyl group,
R ¹³ is a methyl group,
R ⁶ is a chlorine atom,
n is 2,
q is 0, 1 or 2;
A compound wherein p is 0 or 1.

Preferably, the bipyridine compound is the bipyridine compound 7, 8, 11, 12, 14, 15, 64, 69, 84, 104, 184, 204, 300, 303, 304, 306, 318, in the examples described below. 321 or 344.

Next, a method for producing the bipyridine compound will be described.

Examples of the production method of the bipyridine compound include the following production methods.

Manufacturing method 1
In this bipyridine compound, a compound in which n = 1 (hereinafter referred to as the present bipyridine compound (Ib)) and a compound in which n = 2 (hereinafter referred to as the present bipyridine compound (Ic)) are n = 0. (Hereinafter referred to as the present bipyridine compound (Ia)) and an oxidant.

[Wherein the symbols have the same meaning as described above. ]

First, a method for producing the bipyridine compound (Ib) from the bipyridine compound (Ia) will be described.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons).
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid (hereinafter referred to as mCPBA).
In the reaction, an oxidizing agent is usually used in an amount of 1 to 1.2 mol per 1 mol of the bipyridine compound (Ia).
The reaction temperature is usually in the range of −20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash with. The obtained bipyridine compound (Ib) can be obtained by drying and concentrating the obtained organic layer.

Next, a method for producing the bipyridine compound (Ic) from the bipyridine compound (Ib) will be described.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
In the reaction, an oxidizing agent is usually used at a ratio of 1 to 2 moles with respect to 1 mole of the bipyridine compound (Ib).
The reaction temperature is usually in the range of −20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash with. By drying and concentrating the organic layer, the bipyridine compound (Ic) can be obtained.

Moreover, this bipyridine compound (Ic) can be manufactured by one step reaction (one pot) by making this bipyridine compound (Ia) and an oxidizing agent react.
The reaction is carried out according to the method for producing the bipyridine compound (Ic) from the bipyridine compound (Ib) using an oxidizing agent in a proportion of usually 2 to 5 mol with respect to 1 mol of the bipyridine compound (Ia). be able to.

Manufacturing method 2
The bipyridine compound represented by the formula (Id) (hereinafter referred to as the present bipyridine compound (Id)), the bipyridine compound represented by the formula (Ie) (hereinafter referred to as the present bipyridine compound (Ie)), and the formula The bipyridine compound represented by (If) (hereinafter referred to as the present bipyridine compound (If)) can be produced by reacting the bipyridine compound (Ic) with an oxidizing agent.

[Wherein the symbols have the same meaning as described above. ]

The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
In the reaction, the oxidizing agent is usually used in a ratio of 1 to 10 mol per 1 mol of the bipyridine compound (Ic).
The reaction temperature is usually in the range of −20 to 80 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash with. By drying and concentrating the obtained organic layer, this bipyridine compound (Id), this bipyridine compound (Ie), and the mixture of this bipyridine compound (If) can be obtained. This bipyridine compound (Id), this bipyridine compound (Ie), and this bipyridine compound (If) can be isolated by subjecting this mixture to chromatography, recrystallization, and the like.

Production method 3
The bipyridine compound (Ia) includes a compound represented by formula (M-1) (hereinafter referred to as compound (M-1)) and a compound represented by formula (R-1) (hereinafter referred to as compound (R-1)). And) in the presence of a base.

[Wherein V represents a halogen atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include aprotic polar solvents such as dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), and dimethyl sulfoxide (hereinafter referred to as DMSO). (Hereinafter referred to as aprotic polar solvent).
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides).
In the reaction, with respect to 1 mol of compound (M-1), compound (R-1) is usually used at a ratio of 1 to 10 mol, and base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V is preferably a fluorine atom or a chlorine atom.

Manufacturing method 4
The bipyridine compound (Ia) includes a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)). And) in the presence of a base.

[Wherein, V ¹ represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the base used in the reaction include alkali metal carbonates such as potassium carbonate and cesium carbonate (hereinafter referred to as alkali metal carbonates).
In the reaction, with respect to 1 mole of the compound (M-2), the compound (R-2) is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 10 moles.
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method 5
The bipyridine compound represented by the formula (I) (hereinafter referred to as the present bipyridine compound (I)) is composed of the compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) and the formula. It can be produced by reacting a compound represented by (R-3) (hereinafter referred to as compound (R-3)) in the presence of a base.

[Wherein V ² represents a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the base used in the reaction include alkali metal carbonates.
In the reaction, compound (R-3) is usually used in a proportion of 1 to 10 mol, and a base is usually used in a proportion of 0.1 to 5 mol with respect to 1 mol of compound (M-3).
The reaction temperature is usually in the range of −20 ° C. to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water of the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method 6
The bipyridine compound (I) includes a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) and a compound represented by formula (R-4) (hereinafter referred to as compound (R-4)). And) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the base used in the reaction include alkali metal hydrides.
In the reaction, with respect to 1 mol of the compound (M-4), the compound (R-4) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (I) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
In the reaction, V is preferably a fluorine atom.

Manufacturing method 7
A compound represented by the formula (Ig) (hereinafter referred to as the present bipyridine compound (Ig)) can be produced according to the method described below.

[Wherein R ³⁴ , R ³⁵ , and R ³⁶ each independently represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, one or more atoms selected from group D, or Represents a phenyl group which may have a group, or a 5- or 6-membered aromatic heterocyclic group which may have one or more atoms or groups selected from group D, and other symbols have the same meanings as described above Represents. ]

First, Step 1 will be described.
In Step 1, a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)) and a compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) And react.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include alcohols, aprotic polar solvents, and mixtures thereof.
In the reaction, compound (R-5) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the residue obtained by concentrating the reaction mixture is directly used in Step 2.

Next, Step 2 will be described.
The bipyridine compound (Ig) can be produced by reacting the residue obtained in Step 1, methanesulfonyl chloride and triethylamine.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers (hereinafter referred to as ethers) such as tetrahydrofuran and methyl-tert-butyl ether (hereinafter referred to as MTBE).
In the reaction, with respect to 1 mol of the compound (M-5), methanesulfonyl chloride is usually used in a proportion of 1 to 10 mol and triethylamine is usually used in a proportion of 1 to 10 mol.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ig) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method 8
A compound represented by the formula (Ih) (hereinafter referred to as the present bipyridine compound (Ih)) can be produced, for example, according to the following method.

[Wherein the symbols have the same meaning as described above. ]
First, a method for producing a compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)) from compound (M-5) will be described.
Compound (M-6) can be produced by reacting compound (M-5) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)).
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
In the reaction, compound (R-6) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M-6) can be isolated by performing post-treatment operations such as adding sodium bicarbonate water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. .

Next, a method for producing the bipyridine compound (Ih) from the compound (M-6) will be described. This bipyridine compound (Ih) can be produced by reacting compound (M-6) with a halogenating agent.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
Examples of the halogenating agent used in the reaction include N-bromosuccinimide and N-chlorosuccinimide.
In the reaction, benzoyl peroxide may be added as necessary.
In the reaction, with respect to 1 mol of the compound (M-6), the halogenating agent is usually used in a proportion of 1 to 10 mol, and benzoyl peroxide is usually used in the proportion of 0.1 to 0.5 mol.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, sodium methoxide is added to the reaction mixture until the exotherm subsides, then water is added, extraction is performed with an organic solvent, and the organic layer is dried and concentrated, followed by post-treatment operations such as this. The bipyridine compound (Ih) can be isolated.

Manufacturing method 9
Examples of the method for producing the compound represented by the formula (Ii) (hereinafter referred to as the present bipyridine compound (Ii)) include the following methods.

[Wherein R ³⁷ represents a C1-C6 alkyl group, and other symbols have the same meaning as described above. ]
First, Step 1 will be described. A compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) and a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)) are prepared as bases. React in the presence.
Compound (R-7) can be produced according to the method described in WO2009 / 054742.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
Examples of the base used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases).
In the reaction, with respect to 1 mol of compound (M-7), compound (R-7) is usually used at a ratio of 1 to 10 mol, and base is usually used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of −50 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the residue obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer is used in Step 2.

Next, Step 2 will be described.
The bipyridine compound (Ii) can be produced by reacting the residue obtained in Step 1 with ammonia.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include alcohols, water, and mixtures thereof.
As the ammonia used in the reaction, an aqueous ammonia solution, an ammonia methanol solution, or the like can be used.
In the reaction, ammonia is usually used at a ratio of 1 to 100 mol per 1 mol of compound (M-7).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ii) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method 10
The compound represented by the formula (Ij) (hereinafter referred to as the present bipyridine compound (Ij)) is composed of the compound (M-5) and the compound represented by the formula (R-8) (hereinafter referred to as the compound (R-8)). It can be manufactured by reacting.

[Wherein the symbols have the same meaning as described above. ]
In the reaction, a solvent can be used as necessary. Examples of the solvent used in the reaction include an aprotic polar solvent.
In the reaction, compound (R-8) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-5).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ij) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method 11
The compound represented by the formula (Ip) (hereinafter referred to as the present bipyridine compound (Ip)) is the same as the compound represented by the formula (Ik) (hereinafter referred to as the present bipyridine compound (Ik)) and the formula (R-12). ) (Hereinafter referred to as the compound (R-12)) is reacted in the presence of a base.

[Wherein, X ³ represents a fluorine atom, a chlorine atom, or S (O) ₂ R ¹⁵ ; r represents 0, 1 or 2; and other symbols represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the base used in the reaction include alkali metal carbonates and alkali metal hydrides.
In the reaction, with respect to 1 mole of the bipyridine compound (Ik), the compound (R-12) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Ip) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Production method 12
The compound represented by the formula (Im) (hereinafter referred to as the present bipyridine compound (Im)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-9) (hereinafter referred to as the compound (R-9)). It can be manufactured by reacting.
The compound represented by the formula (In) (hereinafter referred to as the present bipyridine compound (In)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-10) (hereinafter referred to as the compound (R-10)). It can be manufactured by reacting.
The compound represented by the formula (Io) (hereinafter referred to as the present bipyridine compound (Io)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-11) (hereinafter referred to as the compound (R-11)). It can be manufactured by reacting.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, nitriles such as acetonitrile (hereinafter referred to as nitriles), aprotic polar solvents, and mixtures thereof.
The reaction can be carried out by adding a base as necessary. Examples of the base used in the reaction include alkali metal carbonates, alkali metal hydrides, organic bases and the like.
In the reaction, when the bipyridine compound (Im) is produced, the compound (R-9) is usually in a ratio of 1 to 10 mol and the base is usually 1 to 10 mol with respect to 1 mol of the bipyridine compound (Ik). It is used in the ratio.
In the reaction, when the present bipyridine compound (In) is produced, the compound (R-10) is usually in a ratio of 1 to 10 mol and the base is usually in an amount of 1 to 10 per 1 mol of the bipyridine compound (Ik) compound. Used in molar proportions.
In the reaction, when the bipyridine compound (Io) is produced, the compound (R-11) is usually in a ratio of 1 to 10 mol and the base is usually 1 to 10 per 1 mol of the bipyridine compound (Ik) compound. Used in molar proportions.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, post-treatment operations such as addition of water to the reaction mixture, extraction with an organic solvent, drying and concentration of the organic layer, and the like are performed, thereby the present bipyridine compound (Im), the present bipyridine compound (In), Or this bipyridine compound (Io) can be obtained.

Production method 13
The compound represented by the formula (Iq) (hereinafter referred to as the present bipyridine compound (Iq)) is composed of the present bipyridine compound (Ik) and the compound represented by the formula (R-13) (hereinafter referred to as the compound (R-13)). In the presence of a base.

[Wherein, B ¹ and B ² each independently represent a nitrogen atom or CR ³³ , and R ³¹ , R ³² , and R ³³ each independently represent a hydrogen atom or one substituent selected from Group D And other symbols have the same meaning as described above. ]
This reaction can be carried out according to the method described in Production Method 11, using compound (R-13) instead of compound (R-12).

Manufacturing method 14
The compound represented by the formula (Is) (hereinafter referred to as the present bipyridine compound (Is)) and the compound represented by the formula (It) (hereinafter referred to as the present bipyridine compound (It)) are prepared according to the following method. Can be manufactured.

[Wherein the symbols have the same meaning as described above. ]

First, a compound represented by formula (Ir) (hereinafter referred to as the present bipyridine compound (Ir)) and a compound represented by formula (R-14) (hereinafter referred to as compound (R-14)) are reacted. A method for producing the present bipyridine compound (Is) is described.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include nitriles.
In the reaction, a base can be used as necessary. Examples of the base used in the reaction include organic bases.
In the reaction, with respect to 1 mole of the bipyridine compound (Ir), the compound (R-14) is usually used at a ratio of 1 to 5 moles and the base at a ratio of 0.1 to 5 moles.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (Is) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

It continues and describes the method of manufacturing this bipyridine compound (It) by making this bipyridine compound (Is) and a base react.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include alcohols, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is used in a proportion of 0.1 to 5 mol with respect to 1 mol of the bipyridine compound (Is).
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the bipyridine compound (It) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Production method 15
This bipyridine compound (Ia) is obtained by reacting a compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) with compound (R-2) in the presence of a base and a reducing agent. Can be manufactured.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the base used in the reaction include alkali metal carbonates.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate.
In the reaction, with respect to 1 mol of compound (M-22), compound (R-2) is usually in a proportion of 1 to 10 mol, base is usually in a proportion of 1 to 10 mol, and reducing agent is usually in a proportion of 1 to 10 mol. It is used in the ratio.
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the bipyridine compound (Ia) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Hereafter, it describes about the manufacturing method of each intermediate body.

Reference manufacturing method 1
Compound (M-1) is a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) and a compound represented by formula (M-9) (hereinafter referred to as compound (M-9)). ) Can be produced by reacting in the presence of a metal catalyst and an inorganic halide.

[Wherein V ³ represents a chlorine atom, a bromine atom or an iodine atom, M represents Sn (n—C ₄ H ₉ ) ₃ , and other symbols have the same meaning as described above. ]
Compound (M-9) can be produced, for example, according to the method described in WO 03/024961 or the method described in Organic Process Research & Development, 2004, 8, 192-200.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene.
Examples of the metal catalyst used in the reaction include palladium catalysts such as tetrakis (triphenylphosphine) palladium (0) and 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride.
Examples of the inorganic halide used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride, and alkali metal chlorides such as lithium chloride and sodium chloride.
In the reaction, with respect to 1 mole of the compound (M-8), the compound (M-9) is usually in a proportion of 1 to 10 moles, the metal catalyst is usually in a proportion of 0.01 to 0.5 mole, an inorganic halide. Is usually used in a proportion of 0.1 to 5 mol.
The reaction temperature is usually in the range of −20 ° C. to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, compound (M-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Reference production method 2
Compound (M-8) is produced by reacting a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with compound (R-3) in the presence of a base. can do.

[Wherein the symbols have the same meaning as described above. ]
The method of reacting compound (M-10) and compound (R-3) is in accordance with the method described in Production Method 5.

Reference manufacturing method 3
Compound (M-3) can be produced by reacting a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) with an acid.

[Wherein R ^x represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons.
Examples of the acid used in the reaction include boron halides such as boron trichloride and boron tribromide.
In the reaction, an acid is usually used at a ratio of 0.1 to 10 mol per 1 mol of the compound (M-11).
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, compound (M-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Reference production method 4
In the compound (M-11), a compound in which n is 0 (hereinafter referred to as the compound (M-11a)), a compound in which n is 1 (hereinafter referred to as the compound (M-11b)), and n A compound in which is 2 (hereinafter referred to as compound (M-11c)) can be produced according to the following method.

[Wherein the symbols have the same meaning as described above. ]
Compound (M-13) described in Reference Production Method 1 is a compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) instead of compound (M-8). It can be produced according to the method.
Compound (M-12) can be obtained by production according to the method described in Heterocycles, 1990, 30, 875-884. A commercially available compound (M-12) may also be used.
Compound (M-11a) can be produced according to the method described in Production Method 3, using Compound (M-13) instead of Compound (M-1).
Compound (M-11b) and Compound (M-11c) can be produced according to the method described in Production Method 1 using Compound (M-11a) instead of Bipyridine Compound (Ia).

Reference production method 5
The compound represented by the formula (M-15) (hereinafter referred to as compound (M-15)) can be produced according to the method described below.

[Wherein the symbols have the same meaning as described above. ]
As the compound (M-15), a compound represented by the formula (M-14) (hereinafter referred to as compound (M-14)) is used in place of the compound (M-5), and the method according to production method 7 is used. It can be manufactured according to.

Reference manufacturing method 6
A compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) is a compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) and a compound. It can be produced by reacting with (R-12) and then reacting with ammonia.

[Wherein the symbols have the same meaning as described above. ]
Compound (M-17) can be produced according to the method described in production method 9, using compound (M-16) in place of compound (M-7).

Reference manufacturing method 7
A compound represented by the formula (M-18) (hereinafter referred to as compound (M-18)) can be produced by reacting compound (M-14) with compound (R-8).

[Wherein the symbols have the same meaning as described above. ]
Compound (M-18) can be produced according to the method described in production method 10, using compound (M-14) instead of compound (M-5).

Reference production method 8
A compound represented by formula (M-19) (hereinafter referred to as compound (M-19)) is a compound represented by formula (M-20) (hereinafter referred to as compound (M-20)). It can be produced by reacting in the presence of an acid.

[Wherein, R ³⁸ represents a halogen atom or OR ¹ , and other symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, alcohols, aprotic polar solvents, water, and mixtures thereof.
Examples of the acid used in the reaction include hydrochloric acid and sulfuric acid.
In the reaction, an acid is usually used at a ratio of 0.1 to 5 mol with respect to 1 mol of the compound (M-17).
The reaction temperature is usually in the range of 0 ° C to 100 ° C. The reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, compound (M-19) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Reference manufacturing method 9
Compound (M-20) includes a compound represented by formula (M-21) (hereinafter referred to as compound (M-21)) and a compound represented by formula (R-16) (hereinafter referred to as compound (R-)). 16).) Can be reacted in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers, hexane, and mixtures thereof.
An example of the base used in the reaction is n-butyllithium.
In the reaction, with respect to 1 mol of compound (M-21), compound (R-16) is usually used at a ratio of 1 to 5 mol, and base is usually used at a ratio of 1 to 5 mol.
The reaction temperature is usually in the range of −78 ° C. to 100 ° C. The reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, compound (M-20) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
Compound (M-21) can be produced by a known method. A commercially available compound (M-21) may also be used.

Reference production method 10
Compound (M-2) and compound (M-22) can be produced by reacting compound (M-1) with a sulfurizing agent.

[Wherein the symbols have the same meaning as described above. ]

The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent.
Examples of the sulfurizing agent used in the reaction include sodium sulfide and sodium hydrogen sulfide.
In the reaction, a sulfurizing agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M-1).
The reaction temperature is usually in the range of −20 ° C. to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, post-treatment operations such as addition of water to the reaction mixture, extraction with an organic solvent, drying and concentration of the organic layer, and the like are carried out to give compound (M-2) and compound (M-22). Obtainable.
In the reaction, V is preferably a fluorine atom or a chlorine atom.

Reference production method 11
In the compound (M-4), a compound in which V is a chlorine atom or a bromine atom (hereinafter referred to as compound (M-4a)), and a compound in which V is a fluorine atom or an iodine atom (hereinafter referred to as compound (M-4b) ) Can be produced according to the method described below.

[Wherein, V ⁴ represents a chlorine atom or a bromine atom, V ⁵ represents a fluorine atom or an iodine atom, and other symbols represent the same meaning as described above. ]
First, a method for producing compound (M-4a) from compound (M-3) is described.
Compound (M-4a) can be produced by reacting compound (M-3) with phosphorus oxychloride or phosphorus oxybromide.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include aromatic hydrocarbons. When using phosphorus oxychloride, phosphorus oxychloride can also be used as a solvent.
In the reaction, phosphorus oxychloride or phosphorus oxybromide is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (M-3).
The reaction temperature is usually in the range of 0 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (M-4a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Next, a method for producing compound (M-4b) from compound (M-4a) will be described.
Compound (M-4b) can be produced by reacting compound (M-4a) with an inorganic fluoride or inorganic iodide.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include nitriles, aprotic polar solvents, and mixtures thereof.
Examples of the inorganic fluoride used in the reaction include potassium fluoride.
Examples of the inorganic iodide used in the reaction include sodium iodide.
In the reaction, an inorganic fluoride or an inorganic iodide is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (M-4a).
The reaction temperature is usually in the range of 0 ° C to 250 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, compound (M-4b) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

Next, specific examples of the bipyridine compound are shown below.

Formula (200)

[Wherein R ²⁰¹ represents R ¹ , R ²⁰² represents R ² , R ²⁰³ , R ²⁰⁴ , and R ²⁰⁵ each independently represent a hydrogen atom or R ³ , R ²⁰⁶ , R ²⁰⁷ , And R ²⁰⁸ each independently represents a hydrogen atom or R ⁶ , and n represents 0, 1, or 2. ]
A compound represented by

In the compound represented by the formula (200), n is 2, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are Tables 1 to 11 Or a bipyridine compound (hereinafter referred to as compound group SX1).

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

Table 8

Table 9

Table 10

Table 11

In the compound represented by the formula (200), n is 1, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are Tables 1 to 11 The bipyridine compound (hereinafter referred to as compound group SX2), which is any combination described in 1.
In the compound represented by the formula (200), n is 0, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are Tables 1 to 11 Or a bipyridine compound (hereinafter referred to as compound group SX3).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX4).

Table 12

Table 13

Table 14

Table 15

Table 16

Table 17

Table 18

Table 19

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , The present bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX5).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX6) in which any combination shown in Table 12 to Table 19 is combined.

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX7) in any combination of Tables 12-19.

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX8).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX9).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX10).

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX11) wherein any combination of Table 12 to Table 19 is combined.

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX12) in any combination of Tables 12-19.

In the compound represented by the formula (200), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX13).

Formula (201)

[Wherein the symbols have the above-mentioned meanings. ]
Compound represented by

In the compound represented by the formula (201), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are any one of those shown in Tables 1 to 11. This bipyridine compound as a combination (hereinafter referred to as compound group SX14).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are a combination of any of Tables 12 to 19 (hereinafter referred to as compound group SX15).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX16).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX17) in any combination of Tables 12-19.

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds of any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX18).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX19).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX20).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , The present bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX21).

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX22) in which any combination shown in Tables 12 to 19 is combined.

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX23) in any combination of Tables 12-19.

In the compound represented by the formula (201), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX24).

Formula (202)

In the compound represented by the formula (202), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are any one of those shown in Tables 1 to 11. This bipyridine compound as a combination (hereinafter referred to as compound group SX25).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX26).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , The present bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX27).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX28) in which any combination shown in Tables 12 to 19 is combined.

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX29) in any combination of Tables 12 to 19;

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are present bipyridine compounds (hereinafter referred to as compound group SX30) in any combination of Tables 12 to 19.

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX31).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX32).

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX33) in any combination of Tables 12-19.

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX34) wherein any combination shown in Tables 12 to 19 is combined.

In the compound represented by the formula (202), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in Tables 12 to 19 (hereinafter referred to as compound group SX35).

Formula (203)

In the compound represented by the formula (203), R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are hydrogen atoms, and R ²⁰¹ and R ²⁰² are any one of those shown in Tables 1 to 11. This bipyridine compound as a combination (hereinafter referred to as compound group SX36).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX37).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , The present bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX38).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are the present bipyridine compounds (hereinafter referred to as compound group SX39) in any combination of Tables 12-19.

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX40) in which any combination shown in Tables 12 to 19 is combined.

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is an ethyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations shown in Tables 12 to 19 (hereinafter referred to as compound group SX41).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3-tetrafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of Tables 12 to 19 and the present bipyridine compound (hereinafter referred to as compound group SX42).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,3,3-pentafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , This bipyridine compound wherein R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination shown in Tables 12 to 19 (hereinafter referred to as compound group SX43).

In the compound represented by formula (203), n is 2, R ²⁰¹ is a 1,1,2,3,3,3-hexafluoropropyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any of the combinations described in Table 12 to Table 19 and the present bipyridine compound (hereinafter referred to as compound group SX44).

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 2,2,3,4,4,4-hexafluorobutyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are bipyridine compounds (hereinafter referred to as compound group SX45) in which any combination shown in Table 12 to Table 19 is combined.

In the compound represented by the formula (203), n is 2, R ²⁰¹ is a 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group, R ²⁰² is a methyl group, R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ and R ²⁰⁸ are any combination of those shown in Tables 12 to 19 (hereinafter referred to as compound group SX46).

Group (a) is a group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroups a-1 include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, fluradixurone, flupyradifurone ), Triflumezopyrim (triflumezopyrim), dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7, hereinafter may be referred to as insecticidal compound α)

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2 includes acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin ), Beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, Empentrin (empe nthrin), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, taufulvali Tau-fluvalinate, halfenprox, heptafluthrin (heptafluthrin), imiprothrin, kadethrin, meperfluthrin, monfluorothrin, permethrin, phenothrin phenothrin), praretrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin, kappa-tefluthrin, tetramethrin ), Tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, furamethrin, metofluthrin, profluthrin, profluthrin (Profluthrin), a group of sodium channel modulators consisting of dimefluthrin.
Subgroup a-3 is a group of GABAergic chloride channel blockers consisting of ethiprole, fipronil and flufiprole, as well as afoxolaner, fluralaner, broflanilide. And a group of GABAergic chloride channel allosteric modulators consisting of flaxametamide.
Subgroup a-4 consists of chlorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, tetraniliprole and cyhalodiamide. , A group of ryanodine receptor modulators.
Subgroup a-5 is composed of alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), Carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC), formethanate, furathiocarb, isoprocarb (MIPC), methiocarb, methomyl , Metolcarb (MTMC), oxamyl (oxamyl), pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC Fine xylylcarb: consisting (xylylcarb MPMC), a group of carbamates acetylcholinesterase (AChE) inhibitors.
Subgroup a-6 is a group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
Subgroup a-7 includes Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium. , Bacillus amyloliquefaciens, Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, urisawai, Pasturia Microbial material consisting of Pasteuria penetrans, Pasturia usgae, Verticillium chlamydosporium and Harpin protein A group.

Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupyrifurone, flupyradifurone ), Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin Cyfluthrin (beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin (cypermet) hrin), alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin, sigma-cypermethrin Phenothrin (cyphenothrin), deltamethrin (deltamethrin), empentrin (empenthrin), esfenvalerate (ethfenvalerate), etofenprox (etofenprox), fenpropatrin (fenpropathrin), fenvalerate (fenvalerate), flucythrinate (flucythrinate), flumethrin (Flumethrin), fulvalinate, tau-fluvalinate, halffenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin , Monfluorothrin, permethrin, phenothrin, prarethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, kappa tefluthrin te ), Tetramethrin, tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, furamethrin, methfluthrin (Metofluthrin), profluthrin, dimefluthrin, ethiprole, fipronil, flufiprole, chlorantranip Chlorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, cyhalodiamide, alanycarb, aldicarb, bendiocarb, benfuracarb (Benfuracarb), butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC), formethanate (Formetanate), furathiocarb, isoprocarb (MIPC), methiocarb, methomyl, metolcarb (MTMC), oxamyl, pirimicarb , Propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb (MPMC), abamectin and fluensulfone , Both of which are known compounds, “MeisterPro Crop Protection Handbook Vol. 100 (2014) "or the like. These compounds can be obtained from commercially available preparations or produced by known methods.
Dichloromesothiaz (CAS registration number: 1263629-39-5), tetraniliprole (CAS registration number: 1229654-66-3), floxamethamide (CAS registration number: 928783-29-3), afoxoranel (CAS registration number: 1093861-60-9), fluralanel (CAS registration number: 864731-61-3), brofuranilide (CAS registration number: 1207727-04-5), fluazaindolizine (CAS registration number: 1254304-22-7), tioxazafen (CAS registration number: 330459-31-9) and insecticidal compound α (CAS registration number: 1689566-03-7) are both known compounds and are disclosed in International Publication Nos. 2011/017342 and 2010/066952. , International Publication No. 2007/026965, International Publication No. 2007/079162, International Publication No. 2005/085216, International Publication No. 2010/018714, International Publication No. 20 No. 0/129500, WO 2006/114400, and by the method described in WO 2012/029672 can be prepared, respectively.
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass・ Usugae (Pasteuria usgae), Verticillium chlamydosporium and Harpin protein are all known microbial materials Obtained from commercially available preparations or obtained by production using a known method. Moreover, these microbial materials can also be obtained from a fungus depository.
As the mycorrhizal fungi, Arbuscular mycorrhizal fungus is preferable, and in particular, bacteria belonging to the genus Gromus, such as Glomus intraradices, Glomus mosseae Glomus aggregatum and Glomus etunicatum are preferred. In addition, these bacterium belonging to the genus Gromas may be used alone or as a mixture of two or more bacteria.

Group (b) is a group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
Subgroup b-1 includes azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole M, epoxy Conoxi (epoxiconazole), etaconazole (etaconazole), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fluquinconazole (
fluquinconazole), quinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, Microbutanil, nuarimol, oxpoconazole, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole ), Prothioconazole, pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triazime Down (triadimefon), triadimenol (triadimenol), consisting of triflumizole (triflumizole), triforine (triforine) and triticonazole (triticonazole), a group of sterol biosynthesis inhibitors.
Subgroup b-2 includes azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fena Minstrobin, flufenoxystrobin, fluoxastrobin, cresoxim-methyl, mandestrobin, methminostrobin, oryastrobine, orysastrobin, Picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb and triclopyricar b) a group of Qo inhibitors (Quinone outside inhibitors) and a group of Qi inhibitors (Quinone inside inhibitors) consisting of cyazofamid and amisulbrom.
Subgroup b-3 consists of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace, A group of RNA polymerase I inhibitors.
Subgroup b-4 includes benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil , Fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane (sax) Thifluzamide, pyraziflumid, pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4 -Yl) pyrazole-4-carboxami (CAS registration number 141573-94-6, hereinafter may be referred to as bactericidal compound β1), 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4- Yl] pyrazole-4-carboxamide (CAS registration number 1352994-67-2, hereinafter may be referred to as bactericidal compound β2), 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindane- 4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7, hereinafter may be referred to as bactericidal compound β3), 3-difluoromethyl-N-[(3R) -7-fluoro -1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS registration number 1513466-73-3, hereinafter may be referred to as bactericidal compound β4) and N-cyclopropi -3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number 1255734-28-1, hereinafter bactericidal compound a group of succinic acid dehydrogenase inhibitors.
Subgroup b-5 includes benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and A group of β-tubulin polymerization inhibitors consisting of ethaboxam.
Subgroup b-6 includes ferbam, mancozeb, maneb, metyram, propineb, thiram, zineb, ziram, captan ), Captafol, folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, quinomethionate or chinomethionat It is a group of multi-acting point contact active compounds consisting of quinomethionate and fluoroimide.
Subgroup b-7 includes dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, variphenate ( A group of cellulose synthesis inhibitors consisting of valifenalate and mandipropamid. .
Subgroup b-8 consists of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin in MAP (mitogen-activated protein) ) / Histidine kinase inhibitor group.
Subgroup b-9 is a group of other fungicides consisting of tolclofos-methyl, oxathiapiprolin, picarbutrazox, fluopicolide and silthiofam. is there.

Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diiconazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole (
fluquinconazole), quinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, Microbutanil, nuarimol, oxpoconazole, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole ), Prothioconazole, pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triazime Triadimefon, triadimenol, triflumizole, triforine, triticonazole, azoxystrobin, coumoxystrobin, dimoxist Robin (dimoxystrobin), enoxastrobin, famoxadone, fenamidone, fenaminstrobin, flufenoxystrobin, fluoxastrobin, cresoxime-methyl ( kresoxim-methyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxyst Bin (pyraoxystrobin), trifloxystrobin, pyribencarb (pyribencarb), triclopyricarb (triclopyricarb), cyazofamid (cyazofamid), amisulbrom (amisulbrom), benalaxyl (benalaxyl), benalaxyl M (benalaxyl-M) furalaxyl), metalaxyl, metalaxyl-M, oxadixyl, ofurace, benodanil, benzovindiflupyr, bixafen, boscalid, carboxy Carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furametpyr, isofetamid, isoprazam, mepronil, Oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, pyraziflumid, pydiflumetofen, benomyl, carbendazim (carbendm) , Fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, dietofencarb, zoxamide, ethaboxam, ferbam, mancoze, mancozeb maneb), metiram, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorotalonyl (chlorot) halonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate, fluoroimide, dimethomorph, dimethomorph ), Pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate, mandipropamid, fenpiclonil, fludioxonil (flupiclonil) fludioxonil, chlozolinate, iprodione, procymidone, vinclozolin, tolclofos-methyl, oxathiapiproline (oxath) iapiprolin), picarbutrazox, fluopicolide, and silthiofam are all known compounds described in FRAC MoA Poster 2015 (Updated Feb 2015 G. Kemmitt) and the like. These compounds can be obtained from commercially available preparations or produced by known methods.
The bactericidal compound β1 and the bactericidal compound β2 are both known compounds, and can be produced by the methods described in International Publication No. 2011/162397, respectively.
The bactericidal compound β3 and the bactericidal compound β4 are both known compounds and can be produced by the methods described in International Publication No. 2012/084812, respectively.
The bactericidal compound β5 is a known compound and can be produced by the method described in International Publication No. 2013/160387.

Preferably, the compound is an insecticidal compound α, clothianidin, dichloromezothiaz, flupirazifuron, imidacloprid, thiacloprid, thiamethoxam, triflumezopyrim, tefluthrin, brofuranilide, fipronil, floxamethamide, chlorantraniliprole, cyantraniliprole, tetra Niliprol, Abamectin, Fluazaindolizine, Thioxazafen, Bacillus amyloliquefaciens, Bacillus films, Difenoconazole, Flutriahol, Ipconazole, Metoconazole, Prothioconazole, Tebuconazole, Tetraconazole, Triazimenol, Tritico Nazole, azoxystrobin, phenamidon, floxastrobin, mandestrobin, picoxystrobin, pirak Strobin, trifloxystrobin, metalaxyl M, metalaxyl, boscalid, fluopyram, flutolanil, fluxapyroxad, penflufen, penthiopyrad, bactericidal compound β2, sedaxane, ethaboxam, thiabendazole, thiuram, fludioxonil, oxathiapiproline, picalbutrazox And one or more compounds selected from the group consisting of silthiofam and tolcrofosmethyl.
Preferably, the compound is clothianidin, imidacloprid, thiamethoxam, difenoconazole, flutriahole, ipconazole, metconazole, prothioconazole, tebuconazole, triazimenol, triticonazole, azoxystrobin, floxastrobin, mandestrobin , Picoxystrobin, pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, fluopyram, flutolanil, fluxapyroxad, penflufen, penthiopyrad, bactericidal compound β2, cedaxane, ethaboxam, fludioxonil and oxathiapiproline It is one or more types of compounds selected from.
Preferably, the compound is an insecticidal compound α, clothianidin, dichloromezothiaz, flupirazifuron, imidacloprid, thiacloprid, thiamethoxam, triflumezopyrim, tefluthrin, brofuranilide, fipronil, floxamethamide, chlorantraniliprole, cyantraniliprole, tetra It is one or more compounds selected from the group consisting of niliprol, abamectin, fluazaindolizine, thioxazaphene, Bacillus amyloliquefaciens and Bacillus films.
Preferably, the compound is one or more compounds selected from the group consisting of clothianidin, imidacloprid and thiamethoxam.
Preferably, the compound is difenoconazole, flutriazole, ipconazole, metconazole, prothioconazole, tebuconazole, tetraconazole, triadimenol, triticonazole, azoxystrobin, fenamidone, floxastrobin, mandest Robin, picoxystrobin, pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, boscalid, fluopyram, flutolanil, fluxapyroxad, penflufen, penthiopyrad, bactericidal compound β2, sedaxane, ethaboxam, thiabendazole, thiuram, fludioxonil, One or more compounds selected from the group consisting of oxathiapiproline, picalbutrazox, silthiofam, and tolcrofosmethyl.
Preferably, the compound is difenoconazole, flutriazole, ipconazole, metconazole, prothioconazole, tebuconazole, triazimenol, triticonazole, azoxystrobin, floxastrobin, mandestrobin, picoxystrobin, One or more selected from the group consisting of pyraclostrobin, trifloxystrobin, metalaxyl M, metalaxyl, fluopyram, flutolanil, floxapyroxad, penflufen, penthiopyrad, bactericidal compound β2, sedaxane, ethaboxam, fludioxonil and oxathiapiproline It is a compound of this.

Below, the example of the combination of this bipyridine compound and this compound in this invention composition is described. However, the abbreviation for SX means “any one of the present bipyridine compounds selected from the compound group SX1 to SX46”.
Acetamiprid + SX, clothianidin + SX, dinotefuran + SX, imidacloprid + SX, nitenpyram + SX, thiacloprid + SX, thiamethoxam + SX, flupiradiflon + SX, sulfoxafurol + SX, triflumezopyrim + SX, dichloromesothiaz compound + SX
Acrinatrin + SX, Aresulin + SX, Bifenthrin + SX, Kappa Bifenthrin + SX, Bioaresulin + SX, Bioresmethrin + SX, Cycloproton + SX, Cyfluthrin + SX, Beta-Cyfluthrin + SX, Cyhalothrin + SX, Gamma Cyhalothrin X SX, Gamma Cyhalothrin X SX + SX, alphacypermethrin + SX, betacypermethrin + SX, thetacypermethrin + SX, zetacypermethrin + SX, sigmacipermethrin + SX, ciphenothrin + SX, deltamethrin + SX, empentrin + SX, esfenvalerate + SX, ethofenprofenprox Thrin + SX, fenvalerate + SX, flucitrinate + SX, flumethrin + SX, fluva Nate + SX, Taufulvalinate + SX, Halfenprox + SX, Heptafluthrin + SX, Imiprothrin + SX, Kadeslin + SX, Meperfluthrin + SX, Monfluorotrin + SX, Permethrin + SX, Phetothrin + SX, Praretrin + SX, Pyrethrin + SX, Pyrethrin + SX Tefluthrin + SX, kappatefluthrin + SX, tetramethrin + SX, tetramethylfurthrin + SX, tralomethrin + SX, transfluthrin + SX, benfurthrin + SX, flufenprox + SX, flumethrin + SX, flamethrin + SX, methfluthrin + SX, proflutriline + SX
Etiprol + SX, fipronil + SX, flupiprol + SX, afoxolanel + SX, fluralanel + SX, brofuranilide + SX, floxamethamide + SX,
Chlorantraniliprole + SX, cyantranylprolol + SX, cyclaniliprol + SX, fulvendiamide + SX, tetraniprolol + SX, cyhalodiamide + SX,
Aranicarb + SX, Aldicarb + SX, Bendiocarb + SX, Benfuracarb + SX, Butcarboxyme + SX, Butoxycarboxyme + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Ethiophene carb + SX, Fenthiocarb + SX, Formethanate + carb, SX Methiocarb + SX, Mesomil + SX, Metorcarb + SX, Oxamyl + SX, Pirimicurve + SX, Propoxyl + SX, Thiodicarb + SX, Thiophanox + SX, Triazamate + SX, Trimetacarb + SX, XMC + SX, Xylylcarb + SX,
Abamectin + SX, fluenesulfone + SX, thioxazaphen + SX, fluazaindolizine + SX,
Mycorrhizal fungi + SX, Arthrobotris dactylides + SX, Bacillus thuringiensis + SX, Bacillus films + SX, Bacillus megaterium + SX, Bacillus amyloliquefaciens + SX, Hilstera rossiliensis + SX, Hilstera minneso Crospodium fimatopagum + SX, Pasteuria Nishizawa + SX, Pasteuria penetrans + SX, Pasteuria Usugae + SX, Verticillium Chlamydosporium + SX, Harpin protein + SX, Arbuscular mycorrhizal fungus + SX, Gross genus + SX, Gross Intraradices + SX, Gross Mosse + SX, Gross Aggregate + SX, Gross Etnicatum + SX,

Azaconazole + SX, Viteltanol + SX, Bromuconazole + SX, Cyproconazole + SX, Difenoconazole + SX, Diniconazole + SX, Diniconazole M + SX, Epoxyconazole + SX, Etaconazole + SX, Fenarimol + SX, Fenbuconazole + SX, Flubuconazole X Flusilazole + SX, flutriazole + SX, hexaconazole + SX, imazalil + SX, imibenconazole + SX, ipconazole + SX, metconazole + SX, microbutanyl + SX, nuarimol + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, pefrazoate + SX , Penconazole + SX, prochloraz + SX, propiconazole + SX, prothiocona Zole + SX, Pyrifenox + SX, Pyrioxazole + SX, Cimeconazole + SX, Tebuconazole + SX, Tetraconazole + SX, Triadimephone + SX, Triadimenol + SX, Triflumizole + SX, Triphorine + SX, Triticonazole + SX,
Azoxystrobin + SX, umoxistrobin + SX, dimoxystrobin + SX, enoxastrobin + SX, famoxadone + SX, phenamidon + SX, phenaminestrobin + SX, fluphenoxystrobin + SX, fluoxastrobin + SX, cresoxime-methyl + SX, Mandestrobin + SX, Metominostrobin + SX, Orissatrobin + SX, Picoxystrobin + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyroxystrobin + SX, Pyribencarb + SX, Triclopyricarb + SX, Cyazofamid + SX, Amisulbrom + SX ,
Benalaxyl + SX, Benalaxyl M + SX, Furaraxyl + SX, Metalaxyl + SX, Metalaxyl M + SX, Oxadixyl + SX, Offrace + SX,
Benodanyl + SX, benzobindiflupyr + SX, bixafen + SX, boscalid + SX, carboxin + SX, fenfram + SX, fluopyram + SX, flutolanil + SX, floxapyradod + SX, furametopyl + SX, isophetamide + SX, isopyrazam + SX, propyram + SX, propyram + SX, propyram + SX , Penthiopyrad + SX, penflufen + SX, sedaxane + SX, tifluzamide + SX, pyraziflumide + SX, pidiflumethofene + SX, bactericidal compound β1 + SX, bactericidal compound β2 + SX, bactericidal compound β3 + SX, bactericidal compound β4 + SX, bactericidal compound β5 + SX,
Benomyl + SX, carbendazim + SX, fuberidazole + SX, thiabendazole + SX, thiophanate + SX, thiophanatemethyl + SX, dietofencarb + SX, zoxamide + SX, ethaboxam + SX,
Felbum + SX, Manzeb + SX, Manneb + SX, Methylam + SX, Propineb + SX, Thiuram + SX, Dinebu and Diram + SX, Captan + SX, Captahole + SX, Holpet + SX, Chlorothalonyl + SX, Tolyl fluanid + SX, Guazatine X , Dithianon + SX, quinomethionate + SX, fluorimide + SX,
Dimethomorph + SX, Flumorph + SX, Pyrimorph + SX, Bench Avaricarb + SX, Bench Avaricarb isopropyl + SX, Iprovaricarb + SX, Varifenalate + SX, Mandipropamide + SX,
Fenpiclonyl + SX, fludioxonil + SX, clozolinate + SX, iprodione + SX, procymidone + SX, vinclozoline + SX, tolcrofosmethyl + SX, oxathiapiproline + SX, picalbutrazox + SX, flupicoride + SX, silthiofam + SX.

The composition of the present invention may be a simple mixture of the present bipyridine compound and the present compound, but usually the present bipyridine compound and the present compound are mixed with an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, Emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, obtained by adding surfactants and other formulation adjuvants as necessary. Smoke agents, poison baits, resin preparations, shampoos, paste preparations, foams, carbon dioxide preparations, tablets and the like. These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
The total content of the bipyridine compound and the compound in the composition of the present invention is usually in the range of 0.1 to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight. .

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate) Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).

Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyrate) Nitriles), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Amides (DMF, N, N-dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate and vegetable oils (soybean oil, cottonseed oil, etc.).

Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.

Other formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthesis Water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxyphenol and 3- Mention may be made of mixtures with tert-butyl-4-methoxyphenol.

Examples of the base material of the resin preparation include vinyl chloride polymers and polyurethanes. These base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, if necessary. A plasticizer such as stearic acid may be added. The resin preparation is obtained by kneading the bipyridine compound and the compound into the base material using a general kneading apparatus, and then performing molding such as injection molding, extrusion molding, press molding, and the like. It can be processed into a resin formulation having a plate shape, a film shape, a tape shape, a net shape, a string shape or the like through processing steps such as molding and cutting. These resin preparations are processed into animal collars, animal ear tags, sheet preparations, attracting laces, and horticultural supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose, and, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, Additives such as pepper, powdered foods for children and pets, cheese flavor, onion flavor, peanut oil and other pest attractant flavors are added.

The content ratio of the present bipyridine compound and the present compound in the composition of the present invention is not particularly limited, but the composition of the present invention is one or more compounds selected from the group (a) (hereinafter referred to as the present compound). a), the ratio of the content of the bipyridine compound and the compound a is preferably in the range of 100: 1 to 1: 100 by weight, in particular 10: 1 to 1:10. The range of is preferable. When the composition of the present invention contains one or more compounds selected from the group (b) (hereinafter referred to as the present compound b), the ratio of the content of the bipyridine compound and the present compound b is preferably The weight ratio is in the range of 10,000: 1 to 1: 100, particularly preferably in the range of 1000: 1 to 1:10, and more preferably in the range of 1000: 1 to 1: 1.

The pest control method of the present invention is carried out by applying an effective amount of the composition of the present invention to pests directly and / or in the habitat of pests. Examples of habitats for pests include plants, soil for cultivating plants, indoors, and animal bodies.

Examples of a method for applying an effective amount of the composition of the present invention to a plant or soil for cultivating a plant include, for example, a method of applying an effective amount of the composition of the present invention to a plant foliage, flower vase, seedling or ear, seed disinfection, A method of applying an effective amount of the composition of the present invention to seeds such as seed soaking and seed coats or bulbs such as seed pods, a method of applying an effective amount of the composition of the present invention to soil before or after planting Is mentioned.

As a method for applying the effective amount of the composition of the present invention to the foliage, flower vase, seedling or ear of a plant, specifically, the effective amount of the composition of the present invention is applied to the surface of the plant such as foliage spraying, tree spraying, etc. In addition, a method of spraying an effective amount of the composition of the present invention to the vase or the whole plant in the flowering period including before flowering, during flowering, and after flowering is mentioned. A method of spraying an effective amount of the composition of the present invention on the panicle or the whole plant is mentioned.

In addition, a method for controlling pests by applying an effective amount of the composition of the present invention to soil before or after planting is intended to protect against damage such as feeding by pests. A method for directly controlling pests by applying an effective amount of the composition of the present invention to the rhizosphere of the crop to be cultivated, or by feeding an effective amount of the composition of the present invention into the plant body from the root or the like to feed the plant It is a method to control the pests.
Examples of a method for applying an effective amount of the composition of the present invention to soil before or after planting a plant include planting treatment (planting hole spraying, planting treatment soil admixture), plant source treatment (strain Former spraying, Strain source soil mixing, Strain source irrigation, Late seedling treatment, Soil planting treatment (Sprouting spray, Sprout soil mixing), Soil treatment (Striping spray, Soil mixing, Growing season crop) Striping), cropping treatment at sowing (spreading at sowing, mixing with soil at sowing), full treatment (spreading all soil, blending with whole soil), side treatment, water surface treatment (water surface application, water surface after flooding) Application), other soil spraying treatments (growth season granule foliar spraying, under-canopy or around trunk trunk, soil surface spraying, soil surface mixing, sowing hole spraying, buttocks surface spraying, inter-plant spraying), other irrigation processing (soil Irrigation, seedling irrigation, chemical infusion treatment, local irrigation, chemical drip irrigation, chemigesi ), Seedling box treatment (spreading seedling box, seedling box irrigation, seedling box chemical solution flooding), seedling tray processing (nursery tray spraying, seedling tray irrigation, seedling tray chemical solution flooding), seedling treatment (seed bed spraying, seed bed irrigation, Water seedling surrogate seedling spraying, seedling soaking), floor soil mixing treatment (floor soil mixing, pre-sowing floor soil mixing, sowing before soil covering before spraying, spraying after soil covering after seeding, soil covering), other treatments (culture soil mixing, seeding, Topsoil mixing, raindrop soil mixing, planting treatment, granule inflorescence spraying, paste fertilizer mixing).

In the present invention, the seed means the seed of the plant in a state before being sown in the soil or the culture medium, and the bulb is a bulb, a bulb, or a tuber of the plant in a state before being planted in the soil or the culture medium. , Rhizome, stem fragment, seed pod and tuberous root. A method for controlling pests by applying an effective amount of the composition of the present invention to seeds or bulbs is, for example, directly applied to seeds or bulbs of plants to be protected from damage such as feeding by pests. A method for controlling pests by applying an effective amount of the above; a method for controlling pests that feed on seeds by applying an effective amount of the composition of the present invention in the vicinity of the seeds or bulbs; or from seeds or bulbs An effective amount of the composition of the present invention is osmotically transferred inside the plant body to control pests that feed on the plant, and a method of applying the effective amount of the composition of the present invention to seeds or bulbs is, for example, , Spraying treatment, smearing treatment, dipping treatment, impregnation treatment, coating treatment, film coating treatment, and pellet coating treatment. Seeds or bulbs that retain an effective amount of the composition of the invention are prepared by these methods.
When the composition of the present invention is applied to seeds or bulbs, the application amount of the bipyridine compound is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of seeds or bulbs. The amount is usually 0.000001 to 50 g, preferably 0.0001 to 30 g per kg of seeds or bulbs.

Examples of the pests for which the composition of the present invention is effective include harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and phytopathogenic fungi such as filamentous fungi and bacteria. Examples of such pests include the following.

Hemiptera pests: Japanese green planthoppers (Laodelphax striatellus), Japanese brown planthoppers (Nilaparvata lugens), white planthoppers (Sogatella furcifera), corn planters (Peregrinus maidis), etc .; Nephotettix (Nephotettix nigropictus), Recipe dorsalis, Emporasca onukii, Potato reef hopper (Empoasca fabae), Corn leaf hopper (Dalbulus maidis), Sugarcane ugicine (Suhana) ), Leafhoppers (Cofana spectra), leafhoppers such as Nephotettix nigropictus; cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), daikona Aphid (Brevicoryne brassicae), snowy aphid (Aphis spiraecola), tulip beetle aphid (Macrosiphum euphorbiae), potato beetle aphid (Aulacorthum solani), wheat aphid (Rhopalosiphum padi), citrus aphid pruni), soybean aphids (Aphis glycines Matsumura), corn aphids (Rhopalosiphum maidis), brown aphids (Tetraneura nigriabdominalis), grape aphids (Viteus vitifoliae), Grapes Phylloxera (Daktulosphaira trixifoxePlleififepelllpelife aphids such as leaf phylloxera (Phylloxera notabilis pergande), Southern pecan leaf phylloxera (Phylloxera russellae Stoetzel); Scotinophara lurida, Malaysia an rice black bug (Scotinophara coarctata), blue beetle (Nezara antennata), bark beetle (Eysarcoris parvus), black beetle (Halyomorpha mista), southern blue beetle (Nezara virstink), Stink bug (Nezara viridula), Red banded stink bug (Piezodorus guildinii), Burrower brown bug (Scaptocoris castanea), Oebalus pugnax, Dichelops melacanthus, and other stink bugs; Leptocorisa acuta, Leptocorisa genus, etc. leucopterus) etc. White lice (Trialeurodes vaporariorum), whitefly (Bemisia tabaci), whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferus), etc .; Citrus snow scale (Unaspis citri), Ruby beetle (Ceroplastes rubens), Icerya scale insect (Icerya purchasi), Fuji scale insect (Planococcus kraunhiae), stag beetle (Pseudococcus longispinis), stag beetle cas pi Scale insects such as Brevennia rehi; pheasants such as diaphorina citri, psylla pyrisuga, potato topiclid (Bactericerca cockerelli); pear Mumbai (Stephanitis nasi) tingidae such as; bedbugs (Cimex lectularius) Bed Bug such as and Giant Cicada (Quesada gigas).

Lepidopterous insects: Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), Trichomyceae (Tryporyza incertulas), Shiromecho (Scirpophaga innotata), Yellow stem borer (Scirpophaga incertulas (Cnaphalocrocis medinalis), Marasmia patnalis, Marasmia exigna, cotton moth (Notarcha derogata), puffer moth (Plodia ア interpunctella), yellow moth (Ostrinia furnacalis), yellow moth (Hellulaedlus moth) depunctalis), Marasmia genus, Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shoot Borer (Epinotia aporema ersuger elchin licus, etc .; Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Spodamia poda frugiperda), Spodoptera exempta, Tamanayaga (Agrotis ipsilon), Tamanaginouba (Plusia nigrisigna), Soybean looper (Pseudoplusia includens), Trichopulsia, Heliothis virescens etc. Heliotis genus Anticarsia gammatalis), Cotton leafworm (Alabama argillacea) and other moths; White butterflies such as Pieris rapae; Adoxofies genus, Grapholita molesta, and Leguminivora glyc inivorella), Azkiyamushiga (Matsumuraeses azukivora), Apple Kokukumonmonaki (Adoxophyes orana fasciata), Chanokokumonmonamiki (Adoxophyes honmai. ), Chamonaki (Homona magnanima), Midarekamonmonaki (Archips fuscocupreanus), Codlinga (Cydia pomonella), etc .; Sink moths such as borer (Ecdytolopha） aurantiana); Coffee Leaf miner (Leucoptera 、 coffeela); gossypiella) Potatoes such as potato moth (Phthorimaea culcula); Hitritris such as Hyphantria cunea.

Common pests: Citrus thrips (Frankliniella occidentalis), Thrips parmi, Scirtothrips dorsalis, Thrips tabici Thrips such as rice thrips (Haplothrips aculeatus) and rice thrips (Stenchaetothrips biformis).

Diptera: Pteris flies (Delia platura), onion flies (Delia antiqua), sugar beet root maggots (Tetanopsemyopaeformis), etc .; ), Leafworms (Liriomyzariotrifolii), leafworms (Chromatomyia horticola), etc .; (Hydrellia philippina) Hydrellia sasakii, etc .; Drosophila, Drosophila, Drosophila, such as Megaselia spiracularis; Drosophila, such as Clogmia albipunctata; Crab fly mushrooms; Hessian flies (Mayetiola destructor), Tamas flies such as Oreseolia oryzae; Diopsis macrophthalma etc .; Frogs such as Common cranefly (Tipula oleracea), European cranefly (Tipula gad)

Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cumber rot balte ), San Antonio Beetle (Diabrotica speciosa), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Cereal Leaf Beetle (Oulema melanopus), Scots beetle (Aulacophora femoralis), Psyllotata s cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryzae) , Grape Colaspice (Colaspis brunnea), Corn Flare Beetle (Chaetocnema pulicaria), Potato Flare Beetle (Epitrix cucumeris), Rice Beetle (Dicladispa armigera), Seedcorn beetle (Stenolophus lecontei), cornbeerons Species: Douganebuoy (Anomala cuprea), Japanese squirrel (Anomala rufocuprea), Japanese beetle (Popillia japonica), European Chafer (Rhizotrogus majalis), carrot beetle (Bothynus gibbosus), Grape colaspis (nealy, asp) Hoetrichia, June beetle (Phyllophaga crinita) and other genus Phyllophaga genus, Diloboderus Di abderus and other dilobodes genus beetles; Weevil such as weevil (Sphenophorus ネ venatus); cotton weevil (Anthonomus grandis), Southern Corn Billbug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus) and Sphenophorus levis ) Epiracunas, such as Lyctus brunneus, Toxus piniperda, etc .; Nagashimushi; Leopard beetle; Anoplophora okinawensis), Agriotes ogurae fuscicollis, and beetles (Melanotus legatus), etc. (Agriotes sp., Aelous sp., Anchastus sp., Melanotus sp. . ; Aoba ants backlash Staphylinidae (Paederus fuscipes) Staphylinidae such as and Coffee Berry Borer (Hypothenemus hampei).

Insect pest: Locusta migratoria, Kera (Gryllotalpa africana), Moroccan terrestrial grasshopper (Dociostaurus maroccanus), Australian terrestrial grasshopper (Chortoicetes terminifera), Red croaker (Nomadacris septemfasciaust ina, Loc) melanorhodon), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes) Grasshopper (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Copaneago (Oxya yezoensis), Red-footed tiger (Oxya japonica), Thai winged locust (Patanga ucci) Green cricket (Acheta domesticus), Emma cricket (Teleogryllusrylemma), Mormon 、 cricket (Anabrus simplex), etc.

Hymenopteran pests: bees such as Athalia rosae and Athalia japonica; fire ants;
Cockroach insects: German cockroach (Blattella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis).

Termite pests: Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), American ants termites (Incisitermes minor), stag termites (Cryptotermes domesticus), ants, termites (Odontotermes eoformosaterm), ants Glypto termes amamianus), Miyatake termite (Reticulitermes miyatakei), Camellia termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Nitobe Roari (Pericapritermes nitobei), warrior termite (Sinocapritermes mushae), Cornitermes cumulans like.

Ticks: spider mites (Tetranychus urticae), spider mites (Tetranychus kanzawai), mandarin spider mites (Panonychus citri), apple spider mites (Panonychus ulmi), spider mites, Southern Turkey spider mites (Brevipalpus phoenicis), etc .; Phyllocoptruta citri, Tomato rustic mite (Aculops lycopersici), Chinese rustic mite (Calacarus carinatus), Chinese cabbage mite (Acaphylla theavagrans), Green radish mite (Eriophyes chibaensis), Mite schist ticks Dust mites such as (Polyphagotarsonemus latus); spider mites such as the southern spider mite (Brevipalpus phoenicis); spider mites; Haemaphysalis longicornis; Tick (Dermacentor taiwanicus), American dog ticks (Dermacentor variabilis), Yamato ticks (Ixodes ovatus), Schulz ticks (Ixodes persulcatus), Black-legged ticks (Ixodes scapularis), American tick ticks (Amblyomma americanum), ophilus tick Ticks such as Rhipicephalus sanguineus; tick such as Tyrophagus putrescentiae; Tyrophagus similis; hey D eruditus), crawfish tick (Cheyletus malaccensis), crayfish tick (Cheyletus moorei), crayfish tick (Cheyletiella yasguri), etc .; Spider mites such as Sacroptes scabiei; Acrid mites such as Dogid mites (Demodex canis); Acarid mites; Tsutsugamushi, such as (Leptotrombidium akamushi).
Spiders: Spiders such as Chiracanthium japonicum and Latrodectus hasseltii.
Lips and legs: Gezi (Thereuonema hilgendorfi), Tobismkade (Scolopendra subspinipes), etc.
Double-legged class: zelkova (Oxidus gracilis), red scallop (Nedyopus tambanus), etc.
Isopods: Armadillidium vulgare, etc.
Gastropoda: Limax marginatus, Limax flavus, Pomacea canaliculata, etc.

Nematode: Aphelenchoides basseyi of Aphelenchoides sp .; Pratylenchusus p neglectus); Meloidogyne javanica, Meloidogyne incognita, Meloidogyne hapla; Heterodera deter (Globodera sp.) Potato cyst nematode (Globodera rostochiensis), Rotylenchulus reniformis, strawberry mesenchu (Nothotylenchus acris), Radopholus similis, Ditilencs gypsashi (Ditylenc) hus dipsaci), Tylenchulus semipenetrans; Longidorus sp .; Xiphinema sp .; Trichodols (Trichodorus sp.); Bursaphelenchus sp. Nematode (Bursaphelenchus xylophilus) etc.

Plant pathogens: Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat udon Disease (Erysiphe graminis), red mold disease (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust disease (Puccinia striiformis, P. graminis, P. recondita), red snow rot (Microdochium nivale, M. majus), Snow rot, Mycobacterium tuberculosis (Typhula sp.), Bare scab (Ustilago tritici), Nagusa scab (Tilletia caries, T. controversa), Eye rot (Pseudocercosporella herpotrichoides), Leaf blight (Septoria tritici) , Dry blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), Rhizoctonia solani, blight (Gaeumannomyces graminis); barley powdery mildew (Erysiphe graminis), red Mold fungus (F usarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust disease (Puccinia striiformis, P.graminis, P.hordei), naked scab (Ustilago nuda), cloud disease (Rhynchosporium secalis), net leaf disease (Pyrenophora) teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), lambaria disease (Ramularia collo-cygni), Rhizoctonia solani (Rhizoctonia solani); corn rust (Puccinia sorghi), southern Rust (Puccinia polysora), soot rot (Setosphaeria turcica), tropical rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-) maydis), brown spot disease (Kabatiella zeae), Faeosphaeria reef spot disease (Phaeosphaeria maydis), diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stoe Lot disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); Cotton anthracnose (Colletotrichum gossypii), mildew (Ramularia areola), black spot (Alternaria macrospora, A. gossypii), Black root rot disease caused by Thielaviopsis (Thielaviopsis basicola); coffee rust (Hemileia vastatrix); leaf spot disease (Cercospora coffeicola); rape myeloid disease (Sclerotinia sclerotiorum); black spot disease (Alternaria brassicae); Disease (Phoma lingam); sugarcane rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); citrus black spot tri (Dia) Common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); apple monili Disease (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose (Glomerella cingulata), brown leaf disease ( Diplocarpon mali), ring rot (Botryosphaeria berengeriana), plague (Phytophtora cactorum); pear scab (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pathotype), red scab (Gymnosporangium haraeanum); Ascidian disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.); Grape black scab (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator) , Rust (Phakopsora ampelopsidis), blacklot (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous leaf (Cercospora kaki, Mycosp) haerella nawae); Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine split disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.), Seedling blight (Pythium sp.); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), subtilis (Pseudocercospora fuligena), plague ( Phytophthora infestans), powdery mildew (Leveillula taurica); eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); cruciferous vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae), root Clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica); spring onion rust (Puccinia allii); soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum va) r. sojae), rust disease (Phakopsora pachyrhizi), brown ring rot (Corynespora cassiicola), anthrax (Colletotrithum glycines, C. truncatum), leaf rot (Rhizoctonia solani), brown rot (Septoria glycines), spot disease (Cercospora sojina), mycorrhizal disease (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); (Sclerotinia sclerotiorum), rust disease (Uromyces appendiculatus), horn spot disease (Phaeoisariopsis griseola), anthrax (Colletotrichum lindemthianum); groundnut black rot (Cercospora personata), brown spot disease (Cercospora arachidicola), white silk disease (Sclerotium rolfsii); Pea powdery mildew (Erysiphe pisi); Potato summer plague (Alternaria solani), plague (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Sp ongospora subterranean f. sp. subterranea), half body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens); strawberry powdery mildew (Sphaerotheca humuli); Elsinoe leucospila), ring spot disease (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); tobacco scab (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague ( Phytophthora nicotianae); Brown spot of sugar beet (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (Aphanomyces cochlioides); black spot of rose (Diplocarpon rosae), powdery mildew Sphaerotheca pannosa); chrysanthemum leaf spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); onion leaf spot (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli) ,small Botrytis squamosa; various crops of gray mold (Botrytis cinerea); mycorrhizal disease (Sclerotinia sclerotiorum); radish black spot disease (Alternaria brassicicola); shiba dull spot disease (Sclerotinia homeocarpa); Brown patch disease and large patch disease (Rhizoctonia solani); and banana Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citiri); carotovora) etc.

The target harmful insects, harmful mites, harmful nematodes and phytopathogenic fungi are insects, mites, insecticides, acaricides, nematicides, fungicides with reduced drug sensitivity or developed drug resistance. Nematodes and phytopathogenic fungi may be used. However, if the drug sensitivity is significantly reduced or the drug resistance is greatly developed, insecticides, acaricides, nematicides and fungicides other than the target insecticides, acaricides, nematicides and fungicides The use of a composition of the invention comprising

The composition of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses.

Examples of plant diseases caused by insect-borne viruses having the control effect of the composition of the present invention include the following.

Rice dwarf disease (Rice waika virus), Tundra disease (Rice tungro spherical virus, Rice tungro bacilliform virus), Rice grassy stunt disease (Rice grassy stunt virus), Rice ragged stunt virus, rice stripe leaf blight Diseases (Rice stripe virus), rice black streaked dwarf virus, rice southern black-streaked dwarf virus, rice gall dwarf virus, rice leaf blight ( Rice hoja blanca virus), White leaf desease of rice, Yellow dwarf virus, Red disease (Rice penyakit merah virus), Rice yellow stunt virus, Transition yellowing Disease (Rice transitory yellowing virus), rice yellow disease (Rice Yellow Mottle Virus), rice necrosis mosaic virus, rice dwarf stunt virus, northern wheat mosaic disease (No rthern Cereal Mosaic Virus), Barley Yellow Dwarf Virus, Wheat yellow dwarf virus, Oat sterile dwarf (Oat sterile dwarf virus), Wheat streak mosaic (Wheat streak mosaic virus)
Maize mosaic disease, Maize stripe disease (maize stripe tenuivirus), Maize chlorotic dwarf (Maize chlorotic dwarf virus), Maize chlorotic mottle (maize chlorotic mottle virus), Maize rayado fino (maize rayado fino marafivirus), Corn stunt (Corn stunt spiroplasma), Maize bushy stunt (Maize bushy stunt phytoplasma), sugar cane mosaic disease (Sugarcane mosaic virus),
Soybean mild mosaic virus, Mosaic disease (Alfalfa Mosaic Virus, Bean yellow-spot mosaic virus, Soybean mosaic virus, Bean yellow mosaic virus, Cowpea severe mosaic virus), Soybean virus disease (Broad bean wilt virus, Bean common mosaic virus, Peanut stunt virus, Southern bean mosaic virus), soybean dwarf luteovirus, Milk-vetch dwarf luteovirus, Bean-pod mottle (Bean-pod mottle virus), Brazilian bud blight (Tobbaco streak virus) ), Cowpea chlorotic mottle (Cowpea chlorotic mottle), Mung bean yellow mosaic (Mung bean yellow mosaic virus), Peanut stripe (Peanut stripe mottle), Soybean crinkle leaf (Soybean crinkle leaf virus), Soybean severe stunt (Soybean severe stunt virus) , Tomato chlorosis virus, Tomato spotted wilt virus, Tomato yellow leaf curl virus, Melon yellow wilt (Melon) yellow spot virus, pumpkin mosaic virus, Cucumber mosaic virus, Zucchini yellow mosaic virus, turnip mosaic virus, cucurbit yellowing disease ( Cucurbit chlorotic yellows virus), Capsicum chlorosis virus, Beet pseudo yellows virus, Chrysanthemum stem necrosis virus, Impatiens necrotic spot virus , Iris yellow spot virus, Sweet potato internal cork virus, Sweet potato shukuyo mosaic virus, Polymixa genus or Olpidium genus Viral disease.

When the composition of the present invention is used for pest control, the application amount can vary widely depending on the application time, application place, application method, etc., but the total amount of the bipyridine compound and the compound is It is usually 1 to 10,000 g per 10,000 m ² . When the composition of the present invention is a preparation such as an emulsion, wettable powder, flowable agent, etc., the composition of the present invention is usually adjusted so that the total concentration of the bipyridine compound and the compound is 0.01 to 10,000 ppm. Is applied diluted with water, and in the case of granules, powders, etc., the composition of the present invention is usually applied as it is.

Examples of plants that can use the composition of the present invention include the following.
Corn, rice, wheat, barley, rye, triticale, oat, sorghum, cotton, soybean, groundnut (peanut), cypress (green beans), lentil, azuki bean, cowpea, mung bean, ladamame, safflower beans, bamboo shoots, moss bean, tepareen beans , Peas, chickpeas, lentils, lupines, pigeons, alfalfa, buckwheat, sugar beet, rape, sunflower, sugarcane, tobacco, etc.
Eggplant vegetable (eggplant, tomato, pepper, pepper, bell pepper, potato), cucumber vegetable (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), cruciferous vegetable (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (eg, leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery) , American Bow Fu etc.), red crustacean vegetables (spinach, chard, etc.), perilla vegetables (shiso, mint, basil, lavender etc.), vegetables such as strawberry, sweet potato, yam, taro,
Fruits (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, oranges, lemons, limes, grapefruits, etc.) , Nuts (chestnuts, walnuts, hazel, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, oysters, olives, loquats, bananas, coffee, dates, Fruit trees such as coconut,
Tea, mulberry, flowering trees, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fus, sycamore, zelkova, kurobe, mominoki, tsuga, nezu, pine, spruce, yew), Flower buds, houseplants, ferns, pastures.

The above-described plant is not limited as long as it is a variety generally cultivated as a crop.

The above-mentioned plant may be a plant bred by a hybrid technique.
Plants bred by hybrid technology are first-generation hybrids obtained by crossing two different varieties of varieties and generally have a hybrid strength (generally, increased yield potential, It is a plant having the characteristics of improving resistance to biological and abiotic stress factors.

The aforementioned plants include genetically modified crops.

The genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutol, ALS (acetolactic acid synthase) inhibitors such as imazetapyr and thifensulfuron methyl, EPSP (5 -Classic breeding with resistance to herbicides such as -enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, dicamba Plants granted by law or genetic engineering techniques are also included.

The above plants can be synthesized by using genetic engineering techniques to synthesize selective toxins known in the genus Bacillus such as Bacillus thuringiensis, and from harmful insects. Also included are plants that can confer specific insecticidal activity by synthesizing gene fragments that partially match the endogenous gene and inducing gene silencing (RNAi; RNA interference) within the target harmful insect body .

In addition, to the above plants, a line provided with two or more traits related to herbicide resistance, pest resistance, disease resistance, etc. as described above using classical breeding technology or genetic recombination technology, and the like Alternatively, a line in which two or more kinds of properties possessed by the parent line are given by crossing genetically modified plants having different characteristics is also included. Examples of such plants include Smart stax (registered trademark).

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples. In the following examples, parts represent parts by weight unless otherwise specified.
First, a manufacture example is shown about manufacture of this bipyridine compound.

Production Example 1-1
A mixture of 1.0 g of 2-chloro-5-hydroxypyridine, 110 mg of potassium hydroxide, 19 mL of methanol, and 19 mL of DMSO was stirred at room temperature under a hexafluoropropene atmosphere for 12 hours. Water was added to the resulting reaction mixture and extracted with MTBE. The obtained organic layer was dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure to obtain 2.0 g of Intermediate 1 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.32 (1H, d), 7.54 (1H, dd), 7.39 (1H, d), 5.15-4.96 (1H, m).

Production Example 1-2
To a mixture of 16 g of 1,4-diazabicyclo [2,2,2] octane and 640 mL of MTBE, 80 mL of a 1.6 M n-butyllithium hexane solution was added dropwise at −45 ° C. in a nitrogen atmosphere. After stirring at −45 ° C. for 2 hours, 11 mL of 3-fluoropyridine was added dropwise to the reaction mixture. The mixture was further stirred at −45 ° C. for 2 hours, cooled to −50 ° C., and 35 mL of tributyltin chloride was added dropwise. After stirring at −50 ° C. for 1 hour, the temperature was raised to room temperature. A saturated aqueous ammonium chloride solution was added to the obtained mixture at room temperature, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The obtained organic layer was concentrated under reduced pressure to obtain 50 g of a mixture containing intermediate 2 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.60-8.56 (1H, m), 7.24-7.19 (1H, m), 7.18-7.12 (1H, m), 1.66-1.47 (6H, m), 1.42-1.23 ( 6H, m), 1.23-1.09 (6H, m), 0.97-0.80 (9H, m).

Production Example 1-3
A mixture of 1.2 g of intermediate 1, 2.5 g of intermediate 2, 500 mg of tetrakistriphenylphosphine palladium (0), 160 mg of copper iodide, 270 mg of anhydrous lithium chloride, and 14 mL of toluene was heated under reflux. Stir for hours. The resulting reaction mixture was allowed to cool to room temperature, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 820 mg of intermediate 3 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, dd), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt).

Production Example 1-4
200 μL of ethanethiol was added dropwise to a suspension of sodium hydride (60%, oily) 110 mg and DMF 5 mL under ice cooling. After stirring for 10 minutes under ice-cooling, a mixture of 820 mg of Intermediate 3 and 5 mL of DMF was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 5 hours. To the obtained reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 680 mg of the present bipyridine compound 9 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.64 (1H, d), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, dd), 7.68 (1H, dd), 7.28 (1H, dd ), 5.18-4.98 (1H, m), 2.92 (2H, q), 1.33 (3H, t).

Production Example 2
To a mixed solution of 530 mg of the present bipyridine compound 9 and 5 mL of chloroform, 520 mg of mCPBA (70%) was added under ice cooling. After stirring for 6 hours under ice-cooling, sodium sulfite and saturated aqueous sodium hydrogen carbonate solution were sequentially added, and the mixture was extracted with chloroform. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 210 mg of the present bipyridine compound 10 represented by the following formula and 340 mg of the present bipyridine compound 11 represented by the following formula.
This bipyridine compound 10

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.60-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 5.18-4.99 (1H, m), 3.52-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
This bipyridine compound 11

¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, dd), 8.53 (1H, d), 8.50 (1H, dd), 7.91 (1H, d), 7.74 (1H, dd), 7.58 (1H, dd ), 5.18-4.99 (1H, m), 3.87 (2H, q), 1.38 (3H, t).

Production Example 3-1
Using 2-bromo-5-methoxypyridine in place of Intermediate 1, Intermediate 4 represented by the following formula was obtained according to the method described in Production Example 1-3.

¹ H-NMR (CDCl ₃ ) δ: 8.57-8.54 (1H, m), 8.51-8.49 (1H, m), 7.96 (1H, dd), 7.56-7.49 (1H, m), 7.35-7.28 (2H, m), 3.94-3.91 (3H, m).

Production Example 3-2
To a mixture of 510 mg of intermediate 4, 110 mg of sodium hydride (oil, 60%), and 5 mL of DMF, 200 μL of ethanethiol was added dropwise under ice cooling. The mixture was warmed to room temperature and stirred for 4 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure.
To a solution obtained by diluting the obtained residue with chloroform, 1.4 g of mCPBA (70%) was added under ice cooling. The reaction mixture was stirred at room temperature for 10 hours. To the obtained reaction mixture, sodium sulfite and saturated aqueous sodium hydrogen carbonate solution were sequentially added, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated sodium hydrogen carbonate, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 490 mg of intermediate 5 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.48 (1H, dd), 8.31 (1H, d), 7.83 (1H, d), 7.51 (1H, dd), 7.36 (1H, dd ), 3.94-3.87 (5H, m), 1.37 (3H, t).

Production Example 3-3
To 5 mL of 1.0 M boron tribromide dichloromethane solution, 490 mg of Intermediate 5 was added under ice cooling. The mixture was warmed to room temperature and stirred for 2 days. To the obtained reaction mixture, a saturated aqueous sodium hydrogen carbonate solution was added under ice cooling, and the mixture was extracted with chloroform. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 300 mg of Intermediate 6 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.50 (1H, dd), 8.12 (1H, d), 7.67 (1H, d), 7.54 (1H, dd), 7.08 (1H, dd ), 6.64 (1H, br s), 3.94 (2H, q), 1.39 (3H, t).

Production Example 3-4
To a mixture of 100 mg of Intermediate 6, 190 mg of cesium carbonate, and 2 mL of DMF, 150 mg of 2,2,3,3-tetrafluoropropyl = trifluoromethanesulfonate (hereinafter referred to as Reagent A) is added under ice cooling. It was. After stirring at room temperature for 10 hours, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 140 mg of the present bipyridine compound 7 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 6.08 (1H, tt), 4.48 (2H, t), 3.89 (2H, q), 1.38 (3H, t).

Production Example 4
Using 2,2,3,3,3-pentafluoropropyl = trifluoromethanesulfonate instead of reagent A, the bipyridine compound 8 represented by the following formula was obtained according to the method described in Production Example 3-4. .

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.87 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.54 (2H, t), 3.89 (2H, q), 1.38 (3H, t).

Production Example 5
In accordance with the method described in Production Example 3-4, 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate is used in place of reagent A, and this bipyridine compound 14 represented by the following formula 14 Got.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.36 (1H, d), 7.87 (1H, d), 7.55 (1H, dd), 7.42 (1H, dd ), 5.33-5.08 (1H, m), 4.59-4.36 (2H, m), 3.89 (2H, q), 1.38 (3H, t).

Production Example 6-1
Intermediate 7 represented by the following formula was obtained according to the method described in Production Example 1-1 using (trifluorovinyl) (trifluoromethyl) ether instead of hexafluoropropene.

¹ H-NMR (CDCl ₃ ) δ: 8.33 (1H, d), 7.55 (1H, dd), 7.39 (1H, d), 5.97 (1H, dt).

Production Example 6-2
Intermediate 8 represented by the following formula was obtained according to the method described in Production Example 1-3 using Intermediate 7 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, d), 8.59 (1H, dd), 8.09 (1H, d), 7.71 (1H, dd), 7.62-7.55 (1H, m), 7.43-7.37 (1H, m), 6.01 (1H, dt).

Production Example 6-3
This bipyridine compound 22 represented by the following formula was obtained according to the method described in Production Example 1-4 using Intermediate 8 instead of Intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, s), 8.45 (1H, dd), 8.10 (1H, d), 7.73 (1H, d), 7.69 (1H, dd), 7.31-7.26 (1H , m), 6.00 (1H, dd), 2.92 (2H, q), 1.33 (3H, t).

Production Example 7
This bipyridine compound 22 was used in place of this bipyridine compound 9, and the bipyridine compound 23 represented by the following formula and the bipyridine compound 24 represented by the following formula were obtained according to the method described in Production Example 2.
This bipyridine compound 23

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, dd), 8.65 (1H, dd), 8.61-8.56 (2H, m), 7.75 (1H, dd), 7.59 (1H, dd), 6.01 (1H , dt), 3.51-3.41 (1H, m), 2.96-2.86 (1H, m), 1.41 (3H, t).
This bipyridine compound 24

¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, dd), 8.54 (1H, d), 8.50 (1H, dd), 7.91 (1H, dd), 7.74 (1H, dd), 7.59 (1H, dd ), 6.00 (1H, dt), 3.87 (2H, q), 1.38 (3H, t).

Production Example 8-1
A mixture of 10 g of 2-bromo-5-hydroxypyridine, 26 g of cesium carbonate, and 29 mL of DMF, 22 g of 2,2,3,3,3-pentafluoropropyl trifluoromethanesulfonate (hereinafter referred to as reagent B) under ice cooling. ) Was added dropwise. The reaction mixture was stirred at room temperature for 2 days, saturated aqueous ammonium chloride solution was added, and the mixture was extracted with MTBE. The obtained organic layer was washed successively with 1M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 17 g of intermediate 9 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, d), 7.45 (1H, d), 7.19 (1H, dd), 4.46 (2H, t).

Production Example 8-2
Intermediate 10 represented by the following formula was obtained according to the method described in Production Example 1-3 using Intermediate 9 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.59-8.55 (1H, m), 8.54 (1H, d), 8.01 (1H, dd), 7.58-7.52 (1H, m), 7.40 (1H, dd), 7.38 -7.33 (1H, m), 4.55 (2H, t).

Production Example 8-3
This bipyridine compound 27 represented by the following formula was obtained according to the method described in Production Example 1-4 using Intermediate 10 instead of Intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.47 (1H, dd), 8.43 (1H, dd), 8.02 (1H, dd), 7.70 (1H, dd), 7.41 (1H, dd), 7.28-7.23 (1H , m), 4.54 (2H, td), 2.91 (2H, q), 1.32 (3H, t).

Production Example 8-4
Instead of the bipyridine compound 9, the bipyridine compound 27 represented by the following formula can be synthesized according to the method described in Production Example 2 using the bipyridine compound 27.
This bipyridine compound 30

Production Example 9-1
Intermediate 18 represented by the following formula was obtained according to the method described in Production Example 8-1 by using reagent A instead of reagent B.

¹ H-NMR (CDCl ₃ ) δ: 8.12 (1H, d), 7.44 (1H, dd), 7.17 (1H, dd), 6.03 (1H, tt), 4.40 (2H, tt).

Production Example 9-2
Intermediate 19 represented by the following formula was obtained according to the method described in Production Example 1-3 using Intermediate 18 instead of Intermediate 1.

¹ H-NMR (CDCl ₃ ) δ: 8.59-8.52 (2H, m), 8.04-7.99 (1H, m), 7.59-7.52 (1H, m), 7.42-7.32 (2H, m), 6.25-5.93 ( 1H, m), 4.54-4.45 (2H, m).

Production Example 9-3
The bipyridine compound 26 represented by the following formula was obtained according to the method described in Production Example 1-4 using the intermediate 19 instead of the intermediate 3.

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, d), 8.43 (1H, dd), 8.00 (1H, d), 7.70 (1H, dd), 7.39 (1H, dd), 7.28-7.23 (1H m), 6.09 (1H, tt), 4.48 (2H, t), 2.91 (2H, q), 1.32 (3H, t).

Production Example 9-4
The bipyridine compound 29 represented by the following formula can be synthesized according to the method described in Production Example 2 using the bipyridine compound 26 instead of the bipyridine compound 9.
This bipyridine compound 29

Production Example 10-1
To a mixture of 100 mL of 1.6 M n-butyllithium hexane solution and 160 mL of THF, a mixture of 23 g of ethyl methyl sulfone and 20 mL of THF was added dropwise at −78 ° C. The reaction mixture was gradually warmed to 0 ° C. and then re-cooled to −78 ° C. To this reaction mixture, a mixture of 20 g of 5-fluoro-2-cyanopyridine and 20 mL of THF was added dropwise at −78 ° C. After gradually warming to room temperature, 2N hydrochloric acid was added to the reaction mixture and stirred for 30 minutes. The obtained mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 40 g of intermediate 16 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.57 (1H, d), 8.19 (1H, dd), 7.62-7.55 (1H, m), 4.97 (2H, s), 3.30 (2H, q), 1.47 (3H , t).

Production Example 10-2
To a mixture of 11 mL of oxalyl chloride and 86 mL of chloroform, 10 mL of DMF was added dropwise under ice cooling. After stirring for 30 minutes under ice cooling, 33 mL of butyl vinyl ether was added dropwise to the mixture. After warming to room temperature and stirring for 2 hours, a mixture of 10 g of Intermediate 16, 42 mL of triethylamine and 30 mL of chloroform was added dropwise to this mixture under ice cooling. The mixture was warmed to room temperature and stirred for 1 hour. The resulting mixture was added to a saturated aqueous ammonium chloride solution and extracted with chloroform. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was diluted with 30 mL of ethanol, and 10 mL of 28% aqueous ammonia solution was added at room temperature. The mixture was heated and stirred at 60 ° C. for 2.5 hours, allowed to cool to room temperature, added to saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 9.4 g of intermediate 17 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, dd), 8.52-8.46 (2H, m), 7.87 (1H, dd), 7.62-7.54 (2H, m), 3.86 (2H, q), 1.38 (3H, t).

Production Example 10-3
To a mixture of 400 mg of Intermediate 17, 90 mg of sodium hydride (60%, oil), and 2 mL of NMP was added 230 mg of 2,2,2-trifluoroethanol under ice cooling. The mixture was heated and stirred at 70 ° C. for 2 days. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 170 mg of the present bipyridine compound 2 represented by the following formula.
This bipyridine compound 2

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.49 (1H, dd), 8.37 (1H, d), 7.86 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.48 (2H, q), 3.89 (2H, q), 1.38 (3H, t).

Production Example 11
To a mixture of 2.0 g of the present bipyridine compound 8, 6 mL of sulfuric acid, and 2 mL of water, 630 μL of 30% aqueous hydrogen peroxide was added under ice cooling. After stirring at room temperature for 2 days, the reaction mixture was added to ice water. The obtained mixture was extracted with chloroform, and the organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.2 g of the present bipyridine compound 204 represented by the following formula, 0.6 g of the present bipyridine compound 214, and 0.2 g of the present bipyridine compound 224.
The bipyridine compound 204

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, dd), 8.37 (1H, dd), 8.04 (1H, d), 7.64 (1H, dd), 7.38 (1H, d), 7.05 (1H, dd ), 4.50 (2H, t), 3.76-3.64 (1H, m), 3.61-3.49 (1H, m), 1.35 (3H, t).
The bipyridine compound 214

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, dd), 8.43 (1H, d), 7.97 (1H, dd), 7.69 (1H, d), 7.50 (1H, dd), 7.43 (1H, dd ), 4.54 (2H, t), 3.44 (2H, q), 1.30 (3H, t).
The bipyridine compound 224

¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, dd), 8.14 (1H, d), 7.91 (1H, dd), 7.57 (1H, dd), 7.42 (1H, d), 7.07 (1H, dd ), 4.51 (2H, t), 3.36-3.18 (2H, m), 1.28 (3H, t).

Production Example 12
15 mL of phosphorus oxychloride was added to a mixture of 6.8 g of the present bipyridine compound 204 and the present bipyridine compound 224 (mixing ratio, the present bipyridine compound 204: this bipyridine compound 224 = 100: 1), and the mixture was heated and stirred at 110 ° C. for 4 hours. . The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform, and a saturated aqueous sodium hydrogen carbonate solution was added. This mixture was extracted with chloroform, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 6.7 g of the present bipyridine compound 169 represented by the following formula and 0.07 g of the present bipyridine compound 194.
The bipyridine compound 169

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.49 (1H, dd), 7.86 (1H, d), 7.56 (1H, dd), 7.42 (1H, d), 4.56 (2H, t ), 3.98 (2H, q), 1.44 (3H, t).
The bipyridine compound 194

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, d), 7.47 (1H, d), 7.42 (1H, d), 7.39 (1H, d), 4.56 (2H, t), 3.70 (2H, q ), 1.40 (3H, t).

Production Example 13
To 3.7 g of the present bipyridine compound 214, 10 mL of phosphorus oxychloride was added, and the mixture was heated and stirred at 110 ° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with chloroform, and a saturated aqueous sodium hydrogen carbonate solution was added. This mixture was extracted with chloroform, and the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.0 g of the present bipyridine compound 79 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.42 (1H, dd), 8.37 (1H, d), 7.91 (1H, d), 7.54 (1H, dd), 7.41 (1H, dd), 4.54 (2H, t ), 3.92 (2H, q), 1.38 (3H, t).

Production Example 14
To a mixture of 500 mg of the present bipyridine compound 79 and 2 mL of DMF, 0.1 mL of 28% sodium methoxide methanol solution was added under ice cooling. After stirring at room temperature for 2 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 230 mg of the present bipyridine compound 94 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.35 (1H, dd), 8.29 (1H, d), 7.83 (1H, dd), 7.40 (1H, dd), 6.88 (1H, d), 4.54 (2H, td ), 4.03 (3H, s), 3.83 (2H, q), 1.36 (3H, t).

Production Example 15
To a mixture of 200 mg of the present bipyridine compound 79 and 2 mL of DMF, 39 mg of 1H-1,2,4-triazole and 22 mg of sodium hydride (60% oil) were added in an ice bath. After stirring at room temperature for 24 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 160 mg of the present bipyridine compound 104 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.23 (1H, s), 8.67 (1H, d), 8.41 (1H, dd), 8.17 (1H, s), 8.10 (1H, d), 7.90 (1H, dd ), 7.47 (1H, dd), 4.57 (2H, td), 3.93 (2H, q), 1.41 (3H, t).

Production Example 16
To a mixture of 200 mg of the present bipyridine compound 79, 0.96 mL of diisopropylethylamine, and 1 mL of acetonitrile, 960 mg of 2-chloro-5- (aminomethyl) thiazole hydrobromide was added under ice cooling. After stirring at 80 ° C. for 5 days, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 200 mg of the present bipyridine compound 89 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.35 (1H, d), 8.12 (1H, d), 7.77 (1H, d), 7.44 (1H, s), 7.40 (1H, dd), 6.52 (1H, d ), 5.40 (1H, t), 4.77 (2H, d), 4.54 (2H, t), 3.77 (2H, q), 1.35 (3H, t).

Production Example 17
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of NMP, 0.09 mL of 28% aqueous ammonia solution was added at room temperature. The reaction mixture was stirred at 80 ° C. for 3 days. After allowing to cool to room temperature, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 110 mg of the present bipyridine compound 59 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.34 (1H, d), 8.13 (1H, d), 7.71 (1H, dd), 7.38 (1H, dd), 6.58 (1H, d), 5.01 (2H, s ), 4.52 (2H, td), 3.66 (2H, q), 1.32 (3H, t).

Production Example 18
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of DMF, 0.13 mL of 50% aqueous dimethylamine solution was added at room temperature. The reaction mixture was stirred at 60 ° C. for 4 hours. After allowing to cool to room temperature, the reaction mixture was subjected to silica gel chromatography to obtain 200 mg of the bipyridine compound 69.

¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.48 (1H, d), 8.37 (1H, d), 7.88 (1H, dd), 7.42 (1H, dd), 4.54 (2H, td ), 3.94 (2H, q), 1.55 (6H, s), 1.40 (3H, t).

Production Example 19
To a mixture of 200 mg of the present bipyridine compound 79 and 1 mL of NMP, 0.2 mL of 2,2,2-trifluoroethylamine was added at room temperature. The reaction mixture was stirred at 120 ° C. for 4 days. After allowing to cool to room temperature, the reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 180 mg of the present bipyridine compound 74 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.34 (1H, d), 8.17 (1H, d), 7.75 (1H, d), 7.40 (1H, dd), 6.61 (1H, d), 5.18 (1H, t ), 4.54 (2H, t), 4.28-4.16 (2H, m), 3.79 (2H, q), 1.36 (3H, t).

Production Example 20
To a mixture of 500 mg of the present bipyridine compound 204, 240 mg of triethylamine, and 3 mL of acetonitrile, 360 mg of trimethylsilylcyanide was added at room temperature. This mixture was heated and stirred at 80 ° C for 34 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with ethyl acetate, and saturated aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 180 mg of the present bipyridine compound 179 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, dd), 8.51 (1H, dd), 8.12 (1H, d), 7.61 (1H, dd), 7.55 (1H, d), 4.66 (2H, t ), 3.90 (2H, q), 1.45 (3H, t).

Production Example 21
5 mL of acetic anhydride was added to 1.0 g of the present bipyridine compound 204, and the mixture was heated and stirred at 100 ° C. for 20 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with ethyl acetate, and saturated aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 980 mg of the present bipyridine compound 174 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.47 (1H, dd), 7.83 (1H, d), 7.55 (1H, dd), 7.47 (1H, d), 4.51 (2H, t ), 3.78 (2H, q), 2.33 (3H, s), 1.36 (3H, t).

Production Example 22
To a mixture of 660 mg of the present bipyridine compound 174 and methanol 7 mL, 600 mg of potassium carbonate was added at room temperature, stirred at room temperature for 1.5 hours, and then adjusted to pH 4 with 2N hydrochloric acid. This mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 530 mg of the present bipyridine compound 159 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 11.08 (1H, s), 8.89 (1H, dd), 8.60 (1H, d), 7.61 (1H, dd), 7.32-7.24 (1H, br m), 7.11 ( 1H, d), 4.71 (2H, t), 3.15 (2H, q), 1.18 (3H, t).

Production Example 23
To a mixture of 340 mg of the present bipyridine compound 159, 400 mg cesium carbonate, and 3 mL DMF, 0.98 mL iodomethane was added at room temperature. After stirring at room temperature for 1 day, the reaction mixture was subjected to silica gel chromatography to obtain 250 mg of the present bipyridine compound 164 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.88 (1H, d), 8.46 (1H, d), 7.57 (1H, dd), 7.34 (1H, d), 7.28 (1H, d), 4.52 (2H, t ), 4.00 (3H, s), 3.62 (2H, q), 1.34 (3H, t).

Production Example 24-1
To a mixture of 30 g of 2-cyano-5-fluoropyridine, 54 g of 2,2,3,3-tetrafluoro-1-propanol, and 90 mL of NMP, 130 g of cesium carbonate was added under ice cooling, and the temperature was raised to room temperature. Stir at room temperature for 1.5 hours. The resulting mixture was heated to 60 ° C. and further stirred at 60 ° C. for 5 hours, and then water was added to the reaction mixture, followed by extraction with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was recrystallized with an isopropanol / hexane solvent to obtain 47 g of an intermediate 11 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, d), 7.71 (1H, dd), 7.33 (1H, dd), 6.04 (1H, tt), 4.49 (2H, t).

Production Example 24-2
To a mixture of 11 g of ethyl methyl sulfone and 50 mL of THF, 59 mL of 1.6 Mn-butyllithium hexane solution was added under ice cooling and stirred for 15 minutes under ice cooling. This mixture was added to a mixture of 20 g of intermediate 11 and 50 mL of THF under ice cooling, and stirred for 10 minutes under ice cooling. This mixture was added to water and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized with an ethyl acetate / hexane solvent to obtain 18 g of intermediate 12 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.36 (1H, d), 7.69 (1H, d), 7.33 (1H, dd), 6.79 (2H, s), 6.05 (1H, tt), 5.28 (1H, s ), 4.48 (2H, t), 3.10 (2H, q), 1.40 (3H, t).

Production Example 24-3
A mixture of 200 mg of intermediate 12 and 2-mL of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one was heated and stirred at 100 ° C. for 4.5 hours. This mixture was subjected to silica gel column chromatography to obtain 100 mg of the present bipyridine compound 53 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.37 (1H, d), 7.99 (1H, d), 7.89 (1H, d), 7.43 (1H, dd), 6.08 (1H, tt ), 4.49 (2H, t), 4.01 (2H, q), 1.41 (3H, t).

Production Example 25-1
In place of 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,3-pentafluoropropanol is used, and is represented by the following formula according to the method described in Production Example 24-1. Intermediate 13 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.46 (1H, d), 7.73-7.71 (1H, m), 7.35 (1H, dd), 4.56 (2H, td).

Production Example 25-2
Intermediate 14 represented by the following formula was obtained according to the method described in Production Example 24-2, using Intermediate 13 instead of Intermediate 11.

¹ H-NMR (CDCl ₃ ) δ: 8.37 (1H, d), 7.69 (1H, d), 7.34 (1H, dd), 6.79 (2H, s), 5.28 (1H, s), 4.54 (2H, t ), 3.10 (2H, q), 1.40 (3H, t).

Production Example 25-3
This bipyridine compound 54 represented by the following formula was obtained according to the method described in Production Example 24-3, using Intermediate 14 instead of Intermediate 12.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, dd), 8.39 (1H, d), 7.99 (1H, dd), 7.89 (1H, d), 7.44 (1H, dd), 4.55 (2H, td ), 4.01 (2H, q), 1.41 (3H, t).

Production Example 26
A mixture of 3.0 g of intermediate 14, 830 μL of acrolein, and 10 mL of ethanol was stirred at 60 ° C. for 2 hours. The mixture was concentrated under reduced pressure to obtain 3.8 g of residue. Of this residue, 500 mg was mixed with 2 mL of THF, and 620 μL of triethylamine and 220 μL of methanesulfonyl chloride were added at room temperature. This mixture was heated and stirred at 60 ° C. for 1 hour. 2N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 47 mg of the present bipyridine compound 99 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.36 (1H, d), 8.30 (1H, d), 7.84 (1H, d), 7.42 (1H, dd), 6.04-5.93 (1H , m), 5.23-5.18 (2H, m), 4.54 (2H, t), 3.87 (2H, q), 3.55 (2H, d), 1.37 (3H, t).

Production Example 27
To a mixture of 8.5 g of intermediate 14 and 30 mL of chloroform, 9.4 g of α- (trifluoromethyl) acryloyl chloride was added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Hexane was added to the mixture and then filtered. The filtrate was added to saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized with an ethyl acetate / hexane solution to obtain 21 g of intermediate 15 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.36 (1H, d), 7.81-7.78 (2H, m), 7.33 (1H, dd), 4.52 (2H, t), 3.49-3.31 (2H, m), 3.11 -3.02 (3H, m), 1.29 (3H, t).

Production Example 28
To a mixture of 10 g of the intermediate 15 and 30 mL of chloroform, 4.4 g of N-bromosuccinimide and 10 mg of benzoyl peroxide were added at room temperature, and the mixture was heated and stirred at 60 ° C. for 30 minutes. The mixture was allowed to cool to room temperature and sodium methoxide was added until the exotherm subsided. Water was added to this mixture and extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 14 g of the bipyridine compound 114 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.45 (1H, d), 8.41 (1H, s), 7.92 (1H, d), 7.41 (1H, dd), 4.57 (2H, t), 3.45 (2H, q ), 1.33 (3H, t).

Production Example 29
23 g of phosphorus oxychloride was added to 4.4 g of the present bipyridine compound 114, and the mixture was stirred for 2 days while heating under reflux. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.7 g of the present bipyridine compound 109 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, s), 8.40 (1H, d), 8.03 (1H, d), 7.44 (1H, dd), 4.56 (2H, t), 4.01 (2H, q ), 1.43 (3H, t).

Production Example 30
To a mixture of 500 mg of the present bipyridine compound 109, 46 mg of 1H-1,2,4-triazole, and 2 mL of DMSO, 240 mg of cesium carbonate was added at room temperature and stirred for 30 minutes. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 240 mg of the present bipyridine compound 154 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.02 (1H, s), 8.99 (1H, s), 8.44 (1H, d), 8.23 (1H, s), 8.01 (1H, d), 7.47 (1H, dd ), 4.58 (2H, t), 4.05 (2H, q), 1.47 (3H, t).

Production Example 31
This bipyridine compound 109 was used in place of the present bipyridine compound 79, and was carried out according to the method described in Preparation Example 17 to obtain the present bipyridine compound 124 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.44 (1H, s), 8.35 (1H, s), 7.78 (1H, d), 7.39 (1H, d), 5.52 (2H, s), 4.53 (2H, t ), 3.79 (2H, q), 1.37 (3H, t).

Production Example 32
This bipyridine compound 109 is used instead of this bipyridine compound 79, 40% methylamine-methanol solution is used instead of the 50% dimethylamine aqueous solution, and the compound represented by the following formula is prepared according to the method described in Production Example 18. Bipyridine compound 129 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.35-8.35 (2H, m), 7.86 (1H, dd), 7.40 (1H, dd), 5.48 (1H, s), 4.54 (2H, td), 3.83 (2H , q), 3.15 (3H, d), 1.37 (3H, t).

Production Example 33
This bipyridine compound 109 was used in place of the present bipyridine compound 79, and was carried out according to the method described in Preparation Example 19 to obtain the present bipyridine compound 139 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.47 (1H, d), 8.36 (1H, d), 7.81 (1H, d), 7.42 (1H, dd), 5.62 (1H, s), 4.55 (2H, t ), 4.42-4.33 (2H, m), 3.89 (2H, q), 1.39 (3H, t).

Production Example 34
To a mixture of 1.0 g of the present bipyridine compound 109, 820 μL of diisopropylethylamine, and 5 mL of THF, 160 μL of hydrazine monohydrate was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 620 mg of the present bipyridine compound 144 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, d), 8.37 (1H, d), 7.82 (1H, d), 7.41 (1H, dd), 6.74 (1H, s), 4.55 (2H, t ), 4.19 (2H, d), 3.80 (2H, q), 1.37 (3H, t).

Production Example 35
To a mixture of 550 mg of the present bipyridine compound 144, 110 μL of pyridine, and 10 mL of acetonitrile, 250 mg of p-toluenesulfonyl chloride was added at room temperature, and the mixture was stirred at room temperature for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 730 mg of the present bipyridine compound 149 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, d), 8.36 (1H, d), 7.71 (1H, d), 7.65 (2H, d), 7.50 (1H, t), 7.41 (1H, dd ), 7.34 (1H, d), 7.00 (2H, d), 4.58 (2H, t), 3.81 (2H, q), 2.29 (3H, s), 1.33 (3H, t).

Production Example 36
To a mixture of 630 mg of the present bipyridine compound 149, 1 mL of water, and 2 mL of ethylene glycol, 78 mg of sodium hydroxide was added at room temperature, and the mixture was stirred at 90 ° C. for 1 hour. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 350 mg of the present bipyridine compound 39 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 9.10 (1H, s), 8.73 (1H, s), 8.40 (1H, d), 7.97 (1H, d), 7.46-7.44 (1H, m), 4.56 (2H , t), 3.99 (2H, q), 1.42 (3H, t).

Production Example 37
This bipyridine compound 109 was used in place of this bipyridine compound 79, and was carried out according to the method described in Preparation Example 14 to obtain the present bipyridine compound 119 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, d), 8.38 (1H, t), 7.90 (1H, dd), 7.42 (1H, dd), 4.55 (2H, t), 4.16 (3H, s ), 3.91 (2H, q), 1.40 (3H, t).

Production Example 38-1
To a mixture of 3.4 g of the intermediate 10 and NMP 36 mL, 5.0 g of sodium hydrogen sulfide n hydrate (manufactured by Wako Pure Chemical Industries, Ltd.) was added at room temperature. The reaction mixture was heated and stirred at 80 ° C. for 12 hours. The resulting reaction mixture was allowed to cool to room temperature, water was added, and 2N hydrochloric acid was further added to adjust to pH 4. The resulting mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated. The resulting solution was stirred at room temperature under an air atmosphere for 12 hours. The obtained solution was subjected to silica gel chromatography to obtain a trace amount of intermediate 20 represented by the following formula and 2.5 g of intermediate 21 represented by the following formula.
Intermediate 20

LC-MS: M + H: 337
Intermediate 21

¹ H-NMR (DMSO-D ₆ ) δ: 8.57 (2H, d), 8.52 (2H, dd), 8.32 (2H, d), 8.05 (2H, dd), 7.78 (2H, dd), 7.41 (2H , dd), 5.06 (4H, t).
LC-MS: M + H: 671

Production Example 38-2
To a mixture of 200 mg of Intermediate 21, 240 mg of potassium carbonate, and 1.2 mL of DMF, 190 mg of (bromomethyl) cyclopropane and 270 mg of sodium hydroxymethanesulfinate dihydrate were sequentially added at room temperature. The reaction mixture was heated to 80 ° C. and stirred for 10 hours. The reaction mixture was allowed to cool to room temperature, aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 150 mg of the present bipyridine compound 279 represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, d), 8.43 (1H, dd), 8.02 (1H, dd), 7.71 (1H, dd), 7.41 (1H, dd), 7.24 (1H, dd ), 4.55 (2H, td), 2.82 (2H, d), 1.07-0.97 (1H, m), 0.63-0.57 (2H, m), 0.31-0.26 (2H, m).

Production Example 38-3
The bipyridine compound 280 represented by the following formula was obtained according to the method described in Production Example 2 using the bipyridine compound 279 instead of the bipyridine compound 9.

¹ H-NMR (CDCl ₃ ) δ: 8.86 (1H, dd), 8.56 (1H, dd), 8.34 (1H, d), 7.88 (1H, d), 7.54 (1H, dd), 7.42 (1H, dd ), 4.54 (2H, td), 3.82 (2H, d), 1.20-1.08 (1H, m), 0.62-0.55 (2H, m), 0.37-0.31 (2H, m).

Production Example 39-1
The following intermediate 22 was obtained according to the method described in Production Example 10-1 using 5-chloro-2-cyanopyridine instead of 5-fluoro-2-cyanopyridine.

¹ H NMR (CDCl ₃ ) δ ppm: 1.47 (3H, t), 3.29 (2H, q), 4.96 (2H, s), 7.87 (1H, dd), 8.08 (1H, dd), 8.68 (1H, dd )

Production Example 39-2
The following intermediate 23 was obtained according to the method described in Production Example 10-2 using the intermediate 22 instead of the intermediate 16.

¹ H NMR (CDCl ₃ ) δ ppm: 1.38 (3H, t), 3.87 (2H, q), 7.57 (1H, dd), 7.81 (1H, dd), 7.85 (1H, dd), 8.49 (1H, dd ), 8.58 (1H, dd), 8.88 (1H, dd)

Production Example 40-1
The following intermediate 24 was obtained according to the method described in Production Example 10-1 using 2-cyano-5-bromopyridine instead of 5-fluoro-2-cyanopyridine.

¹ H-NMR (CDCl ₃ ) δ: 8.79 (1H, d), 8.04-7.98 (2H, m), 4.97 (2H, s), 3.28 (2H, q), 1.46 (3H, t).

Production Example 40-2
The following intermediate 25 was obtained according to the method described in Production Example 10-2 using the intermediate 24 instead of the intermediate 16.

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, dd), 8.68 (1H, d), 8.49 (1H, dd), 8.01-7.98 (1H, m), 7.74 (1H, d), 7.56 (1H , dd), 3.86 (2H, q), 1.37 (3H, t).

Production Example 41-1
In place of 5-fluoro-2-cyanopyridine, 2-cyano-5- (2,2,3,3-tetrafluoropropoxy) pyridine was used, and according to the method described in Production Example 10-1, the following Intermediate 25 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.43 (1H, d), 8.16 (1H, d), 7.38 (1H, dd), 6.05 (1H, tt), 4.96 (2H, s), 4.52 (2H, t ), 3.29 (2H, q), 1.47 (3H, t).

Production Example 41-2
This bipyridine compound 7 was obtained according to the method described in Production Example 10-2, using Intermediate 25 instead of Intermediate 16.

Production Example 42-1
In place of 5-fluoro-2-cyanopyridine, 2-cyano-5- (2,2,3,3,3-pentafluoropropoxy) pyridine was used and according to the method described in Production Example 10-1, The following intermediate 26 was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.44 (1H, t), 8.16 (1H, dd), 7.39 (1H, dd), 4.96 (2H, s), 4.58 (2H, td), 3.29 (2H, q ), 1.47 (3H, t).

Production Example 42-2
The bipyridine compound 8 was obtained according to the method described in Production Example 10-2 using the intermediate 26 instead of the intermediate 16.

Formula (200)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination shown in Tables 20 to 38 below. ] Can be manufactured according to the above-mentioned method.

Table 20

Table 21

Table 22

Table 23

Table 24

Table 25

Table 26

Table 27

Table 28

Table 29

Table 30

Table 31

Table 32

Table 33

Table 34

Table 35

Table 36

Table 37

Table 38

Formula (201)

[Wherein R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination shown in Table 39 below. ] Can be manufactured according to the above-mentioned method.

Table 39

Formula (202)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination shown in Table 40 below. ] Can be manufactured according to the above-mentioned method.

Table 40

Formula (203)

[Wherein, R ²⁰¹ , R ²⁰² , R ²⁰³ , R ²⁰⁴ , R ²⁰⁵ , R ²⁰⁶ , R ²⁰⁷ , R ²⁰⁸ , and n represent any combination shown in Table 41 below. ] Can be manufactured according to the above-mentioned method.

Table 41

The physical property values are shown below.

Table 42

Table 43

Table 44

Table 45

Table 46

Table 47

Table 48

Table 49

Table 50

Table 51

Next, formulation examples are shown.

Formulation Example 1
5 parts of one of the bipyridine compounds 1 to 347, 10 parts of clothianidin, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 100 parts by mixing water Then, each preparation is obtained by fine pulverization by a wet pulverization method.

Formulation Example 2
By thoroughly pulverizing and mixing 10 parts of the present bipyridine compounds 1 to 347, 10 parts of clothianidin, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 75 parts of synthetic silicon hydroxide, Get the agent.

Formulation Example 3
1 part of the bipyridine compounds 1 to 347, 0.5 part of clothianidin, 1 part of synthetic hydrous silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65.5 parts of kaolin clay are mixed. . Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
Formulation Example 4
One part of the present bipyridine compounds 1 to 347, 10 parts of clothianidin, 2 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol were mixed and pulverized by a wet pulverization method. An aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make the total amount 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.

Formulation Examples 5 to 73
In Formulation Example 1, instead of 10 parts of clothianidin, the same operations as in Formulation Example 1 were carried out except that the respective compounds and amounts used in Table i were used to obtain each formulation.
Table i

Table i (continued)

Formulation Examples 74-142
In Formulation Example 2, instead of 10 parts of clothianidin, the same operation as in Formulation Example 2 was carried out except that the respective compounds and amounts used in Table ii were used to obtain each formulation.

Table ii

Table ii (continued)

Formulation Examples 143 to 211
In Formulation Example 3, instead of 0.5 part of clothianidin, the same operations as in Formulation Example 3 were performed except that the respective compounds and amounts used in Table iii were used to obtain each formulation.

Table iii

Table iii (continued)

Formulation Examples 212 to 241
In Formulation Example 4, in place of 2 parts of clothianidin, the same operations as in Formulation Example 4 were carried out except that the respective compounds and amounts used in Table iv were used to obtain each formulation.

Table iv

Formulation Example 242
After mixing 10 parts of the bipyridine compounds 1 to 347, 0.1 part of tebuconazole, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, the mixture is pulverized by a wet pulverization method. Into this, an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to make a total amount of 90 parts, and further 10 parts of propylene glycol is added and stirred and mixed to obtain each preparation.

Formulation Examples 243 to 280
In Formulation Example 242, the same operation as in Formulation Example 242 was carried out except that each compound and the amount used in Table v were used instead of 0.1 part of tebuconazole to obtain each formulation.

Table v

Next, the pest control effect of the composition of the present invention is shown by test examples.

Test example 1
The bipyridine compound is dissolved in 10 mg of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) with respect to 1 mg of the bipyridine compound. Water containing 0.02% by volume of a spreading agent is added thereto, and a chemical solution containing the bipyridine compound is prepared so that the concentration of the bipyridine compound becomes a predetermined concentration.
The compound is dissolved in 10 mg of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) with respect to 1 mg of the compound. Water containing 0.02% by volume of a spreading agent is added thereto, and a chemical solution containing the present compound is prepared so that the concentration of the present compound becomes a predetermined concentration. When using a commercial preparation containing the present compound, each commercial preparation is mixed with water containing 0.02% by volume of a spreading agent, and the present compound is contained so that the concentration of the present compound becomes a predetermined concentration. Prepare the drug solution.
A chemical solution containing the present bipyridine compound and a chemical solution containing the present compound are mixed to prepare a test chemical solution.
Cucumber sativus cotyledon leaf pieces (1.5 cm in length) are accommodated in each well of a 24-well microplate, and 2 cotton aphid adults and 8 larvae are released per well for the test per well. Spray 20 μL of chemical solution. This is the treatment area.
In addition, let the well which sprayed 20 microliters of water containing 0.02 volume% of spreading agents instead of the chemical | medical solution for a test be an untreated section.
After the drug solution for test is dried, the upper part of the microplate is covered with a gas permeable film sheet (trade name: AeroSeal, manufactured by Excel Scientific Inc.), and the number of viable insects in each well is examined 5 days after release.
The control values for the treated and untreated areas are calculated from
Control value (%) = {1− (Tai) / (Cai)} × 100
In addition, the character in a formula represents the following meaning.
Cai: Number of surviving insects at the time of the survey in the untreated area Tai: Number of surviving insects at the time of the survey in the treated area

Results of tests conducted according to Test Example 1 are shown below. The composition of the present invention in which the concentrations of the present bipyridine compound and the present compound are those shown in Table 52 below exhibit excellent control efficacy.

Table 52

Table 52 (continued)

Table 52 (continued)

Table 52 (continued)

Table 52 (continued)

Table 52 (continued)

Table 52 (continued)

Test example 2
The bipyridine compound was dissolved in 10 mg of a mixed solution of xylene: DMF: surfactant (Solpol 3005X, manufactured by Toho Chemical Industry Co., Ltd.) = 4: 4: 1 (volume ratio) with respect to 1 mg of the bipyridine compound. To this, 0.02 vol% water containing a spreading agent (Cindine (registered trademark), manufactured by Sumitomo Chemical Co., Ltd.) is added, and a chemical solution containing the bipyridine compound is added so that the concentration of the bipyridine compound becomes a predetermined concentration. Prepared.
This compound was dissolved in 1 mg of this compound using 10 μL of a mixed solution of xylene: DMF: surfactant (Solpol 3005X, manufactured by Toho Chemical Industry Co., Ltd.) = 4: 4: 1 (volume ratio). To this was added 0.02% by volume of a spreading agent (Sindyne (registered trademark), manufactured by Sumitomo Chemical Co., Ltd.), and a chemical solution containing this compound was prepared so that the concentration of this compound would be a predetermined concentration. . When a commercial preparation containing the present compound is used, each commercial preparation is mixed with water containing 0.02% by volume of a spreading agent (Cyndine (registered trademark)), and the concentration of the present compound becomes a predetermined concentration. Thus, the chemical | medical solution containing this compound was prepared.
The chemical solution containing the present bipyridine compound and the chemical solution containing the present compound were mixed to prepare a test chemical solution.
Cucumber sativus cotyledon leaf pieces (1.5 cm in length) are accommodated in each well of a 24-well microplate, and 2 cotton aphid adults and 8 larvae are released per well for the test per well. 20 μL of chemical solution was sprayed. This was designated as a treatment zone.
In addition, the well which sprayed 20 microliters of water containing 0.02 volume% of spreading agents (Cyndine (trademark)) instead of the chemical | medical solution for a test was made into the no-treatment group.
After the drug solution for testing was dried, the upper part of the microplate was covered with a gas permeable film sheet (trade name: AeraSeal, manufactured by Excel Scientific Inc.), and the number of surviving insects in each well was examined 5 days after release.
The control values for the treated and untreated areas were calculated from
Control value (%) = {1− (Tai) / (Cai)} × 100
In addition, the character in a formula represents the following meaning.
Cai: Number of surviving insects at the time of the survey in the untreated area Tai: Number of surviving insects at the time of the survey in the treated area

Results of tests conducted according to Test Example 2 are shown below. The present bipyridine compound and the composition of the present invention in which the respective concentrations of the present compound are the concentrations shown in Tables 53 to 71 below showed excellent control efficacy.

Table 53

Table 53 (continued)

Table 54

Table 54 (continued)

Table 55

Table 55 (continued)

Table 56

Table 57

Table 57 (continued)

Table 58

Table 59

Table 60

Table 60 (continued)

Table 61

Table 62

Table 63

Table 64

Table 65

Table 66

Table 67

Table 68

Table 69

Table 70

Table 71

The pest control composition of the present invention can be used to control pests.

Claims

A compound represented by the following formula (I) or an N oxide compound thereof;
A pest control composition comprising one or more compounds selected from the group consisting of the following group (a) and the following group (b).
Formula (I):

[Where:
R 1 is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, one or more halogen atoms (C1-C5 alkoxy), a C2-C5 alkyl group, and one or more halogen atoms. (C1-C5 alkylsulfanyl) C2-C5 alkyl group, having one or more halogen atoms (C1-C5 alkylsulfinyl) C2-C5 alkyl group, having one or more halogen atoms (C1-C5 alkylsulfonyl) C2-C5 An alkyl group, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G, or a C3-C7 cycloalkyl group having one or more substituents selected from group G;
R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
R 3 each independently has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, and one or more substituents selected from group D. Or a phenyl group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, OR 12 , NR 11 R 12 , NR 11a R 12a , NR 24 NR 11 R 12 , NR 11 C (O) R 13 , NR 24 NR 11 C (O) R 13 , NR 11 C (O) OR 14 , NR 24 NR 11 C (O) OR 14 , NR 11 C (O) NR 15 R 16 , NR 24 NR 11 C (O) NR 15 R 16 , N = CHNR 15 R 16 , N = S (O) x R 15 R 16 , S (O) y R 15 , C (O) OR 17 , C (O) NR 11 R 12 , a cyano group, a nitro group, or a halogen atom,
R 6 is each independently a C1-C6 alkyl group optionally having one or more halogen atoms, OR 18 , NR 18 R 19 , C (O) OR 25 , OC (O) R 20 , cyano Represents a group, a nitro group, or a halogen atom,
R 11 , R 17 , R 18 , R 19 , R 20 , R 24 , and R 25 are each independently a hydrogen atom or a C1-C6 chain hydrocarbon optionally having one or more halogen atoms Represents a group,
R 12 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or S (O) 2 represents R 23 ,
R 23 represents a C1-C6 chain hydrocarbon group which may have one or more halogen atoms, or a phenyl group which may have one or more substituents selected from group D;
R 11a and R 12a are taken together with the nitrogen atom to which they are attached to form a 3-7-membered non-aromatic heterocyclic group (the 3-7-membered non-aromatic heterocyclic ring is an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline Ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring , An isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepan ring, which may have one or more substituents selected from Group E. },
R 13 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D Represents a 5- or 6-membered aromatic heterocyclic group optionally having
R 14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms. The optionally substituted (C3-C6 cycloalkyl) C1-C3 alkyl group or the phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group has one or more substituents selected from group D; You may do it. },
R 15 and R 16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms,
n and y each independently represents 0, 1, or 2;
x represents 0 or 1;
p and q each independently represent 0, 1, 2, or 3, and when p is 2 or 3, a plurality of R 6 may be the same or different, and q is 2 or 3 In this case, the plurality of R 3 may be the same or different.
Group B: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms A C3-C6 alkynyloxy group which may have one or more halogen atoms, a C1-C6 alkylsulfanyl group which may have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may have one or more halogen atoms, one or more A group consisting of a C1-C6 alkylsulfonyl group optionally having a halogen atom, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.
Group D: C1-C6 chain hydrocarbon group which may have one or more halogen atoms, hydroxy group, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a sulfanyl group, or a C1-C6 which may have one or more halogen atoms. C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR 21 , NR A group consisting of 21 R 22 , C (O) R 21 , OC (O) R 21 , C (O) OR 21 , a cyano group, a nitro group, and a halogen atom. {R 21 and R 22 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms}
Group E: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms A group consisting of a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group and a nitro group.
Group F: C1-C6 alkoxy group optionally having one or more halogen atoms, NHR 21 , NR 21 R 22 , cyano group, phenyl optionally having one or more substituents selected from Group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group A group consisting of a 3-7-membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
Group C: C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of an optionally substituted C3-C6 alkenyloxy group, an optionally substituted C3-C6 alkynyloxy group, and a halogen atom.
Group G: A group consisting of a halogen atom and a C1-C6 haloalkyl group. ]
Group (a):
A group consisting of the following subgroups a-1, a-2, a-3, a-4, a-5, a-6 and a-7.
Subgroup a-1:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, flupiradifurone, sulfoxafurol, triflumezopyrim, dichloromesothiaz and the following formula

The group which consists of a compound shown by these.
Subgroup a-2:
Acrinatrin, Aleslin, Bifenthrin, Kappabifenthrin, Bioarethrin, Bioresmethrin, Cycloproton, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, Gamma Cyhalothrin, Lambdacyhalothrin, Cypermethrin, Alpha Cypermethrin, Betacypermethrin, Theta Permethrin, zeta-cypermethrin, sigma-permethrin, ciphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, fluvinate, taufulvalinate, halfenprox, hepta Flutrin, imiprothrin, cadreslin, meperfluthrin, monfluorotrin, permethrin, phenothrin Prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, kappa Te full Trinh, tetramethrin, tetramethyl full Trinh, tralomethrin, transfluthrin, Benfurutorin, full Fen flufenprox, flumethrin, furamethrin, metofluthrin, the group consisting of profluthrin and dimefluthrin.
Subgroup a-3:
A group consisting of etiprol, fipronil, flufiprolol, afoxolanel, fluralanel, brofuranilide and floxamethamide.
Subgroup a-4:
A group consisting of chlorantraniliprole, cyantranylprolol, cyclaniliprol, fulvendiamide, tetraniprolol and cyhalodiamide.
Subgroup a-5:
Alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiophene carb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, metolcarb, oxamyl, pyrimicarb, dioxycarb, propoxyl Group consisting of thiophanox, triazamate, trimetacarb, XMC and xylylcarb.
Subgroup a-6:
A group consisting of abamectin, fluenesulfone, thioxazaphene and fluazaindolizine.
Subgroup a-7:
Mycorrhizal fungi, Arthrobotris dacteroides, Bacillus thuringiensis, Bacillus films, Bacillus megaterium, Bacillus amyloliquefaciens, Hilstera rosiliensis, Hilstera minnesotensis, Monacrosporium fimatopagum, Pasteurian nisawae , Pasteuria penetrans, Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.
Group (b):
A group consisting of the following subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9.
Subgroup b-1:
Azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, dinicoazole, diniconazole M, epoxiconazole, etaconazole, phenalimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriazole, hexaconazole, imazalil, Imibenconazole, ipconazole, metconazole, microbutanyl, nuarimol, oxpoconazole, oxpoconazole fumarate, pefazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole, cimeconazole, tebuconazole, tetrabuconazole Conazole, triadimephone, triadimenol, triflumizole, trifolin and tritico A group consisting of nasol.
Subgroup b-2:
Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, fluphenoxystrobin, floxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, A group consisting of orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, cyazofamide and amisulbrom.
Subgroup b-3:
A group consisting of benalaxyl, benalaxyl M, furaxyl, metalaxyl, metalaxyl M, oxadixyl and oflase.
Subgroup b-4:
Benodanyl, benzobindiflupyr, bixaphene, boscalid, carboxin, fenfram, fluopyram, flutolanil, fluxapyroxad, furametopyr, isophetamide, isopyrazam, mepronil, oxycarboxyl, pentiopyrad, penflufen, cedaxane, tifluzamide, pyradiflumide Phen, 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide, 3-difluoromethyl-1-methyl-N-[(3R) -1 , 1,3-Trimethylindan-4-yl] pyrazole-4-carboxamide, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4 -Carboxa 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide and N-cyclopropyl-3- (difluoro A group consisting of (methyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide.
Subgroup b-5:
The group consisting of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide and ethaboxam.
Subgroup b-6:
A group consisting of felbam, manzeb, manneb, methyle, propineb, thiuram, dineb, ziram, captan, captahol, holpet, chlorothalonil, tolylfluanid, guazatine, iminotadine, anilazine, dithianone, quinomethionate and fluorimide.
Subgroup b-7:
A group consisting of dimethomorph, flumorph, pyrimorph, bench avaricarb, bench avaricarb isopropyl, iprovaricarb, varifenalate and mandipropamide.
Subgroup b-8:
A group consisting of fenpiclonyl, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.
Subgroup b-9:
The group consisting of toluclophosmethyl, oxathiapiproline, picalbutrazox, fluopicolide and silthiofam.
A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) The pesticidal composition according to claim 1, wherein the ratio of is from 100: 1 to 1: 100 by weight.
A content of one or more compounds selected from the group (a), the compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (a) 2. The pest control composition according to claim 1, wherein the ratio of is 10: 1 to 1:10 by weight.
A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pesticidal composition according to claim 1, wherein the ratio is from 10,000: 1 to 1: 100 by weight.
A content of one or more compounds selected from the group (b), a compound represented by the formula (I) or an N oxide compound thereof, and one or more compounds selected from the group (b) The pesticidal composition according to claim 1, wherein the ratio of is from 1000: 1 to 1:10 by weight.
A method for controlling pests, comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to pests or habitats of pests.
A method for controlling pests, which comprises a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to a plant or soil for growing the plant.
A method for controlling pests, which comprises a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to seeds or bulbs.
Seeds or bulbs holding an effective amount of the pest control composition according to any one of claims 1 to 5.