WO2017090654A1

WO2017090654A1 - Pest control composition and use thereof

Info

Publication number: WO2017090654A1
Application number: PCT/JP2016/084737
Authority: WO
Inventors: 慎哉西村
Original assignee: 住友化学株式会社
Priority date: 2015-11-26
Filing date: 2016-11-24
Publication date: 2017-06-01
Also published as: JP2017036339A

Abstract

The present invention provides a pest control composition which includes a compound represented by formula (1) (in the formula, each symbol is as defined in the description), and at least one compound selected from group (a) or group (b), and which exhibits excellent pest control efficacy.

Description

Pest control composition and use thereof

The present invention relates to a pest control composition and use thereof.

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 formula (1) and one selected from the group (a) or the group (b) It has been found that a composition containing the above compounds has an excellent control effect against pests.

The present invention is as follows.
[1]
Formula (1):

[Where:
A ¹ represents a nitrogen atom or CR ⁴ ;
A ² and A ³ are those in which A ² represents a nitrogen atom and A ³ represents CR ^3b , or A ² represents CR ^3a and A ³ represents a nitrogen atom,
Q represents an oxygen atom or a sulfur atom,
G is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group having one or more halogen atoms, one or more (C3-C5 alkenyl) -O— (C2-C5 alkyl) group having a halogen atom, (C3-C5 alkynyl) -O— (C2-C5 alkyl) group having one or more halogen atoms, one or more halogen atoms (C1-C5 alkyl) -S (O) _m- (C2-C5 alkyl) group having one or more, (C3-C5 alkenyl) -S (O) _m- (C2-C5 alkyl) group having one or more halogen atoms A (C3-C5 alkynyl) -S (O) _m- (C2-C5 alkyl) group having one or more halogen atoms, or a (C1-C5 alkyl) -C having one or more halogen atoms (O)-(C1-C5 alkyl) group,
R ¹ represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
R ² is one or more halogen atoms which may have a C1-C6 chain hydrocarbon group, one or more atoms a phenyl group which may have a group selected from the group A, selected from the group B Any of the five-membered aromatic heterocyclic groups selected from the group C (the five-membered aromatic heterocyclic group may have one or more atoms or groups selected from the group A). 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), any one of groups 3- 7-membered non-aromatic heterocyclic group (The 3-7-membered non-aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups. ^{^{), OR 7, NR 8 R}} 9, NR 8 C (O) R 10, NR 8 C (O) OR 11, NR 8 C (O) NR 12 R 13 ^{^{N = CHNR 12 R 13, N}} = S (O) x R 12 R 13, S (O) y R 12, C (O) OR 8, cyano group, or a halogen atom,
R ⁴ represents a hydrogen atom or a halogen atom,
R ³ , R ^3a and R ^3b each independently represent a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen atom;
R ⁷ has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms An optionally (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group is one or more atoms selected from group A or May have.) Represent,
R ⁸ represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C3-C6 alkynyl group optionally having,
R ⁹ has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) _y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, C1-C6 alkyl group having one cyano group, phenyl C1-C3 alkyl group (the phenyl of the phenyl C1-C3 alkyl group) The minute may have one or more atoms or groups selected from group A), or (5- or 6-membered heteroaryl) C1-C6 alkyl group (the (5- or 6-membered heteroaryl) C1-C6 The 5- or 6-membered heteroaryl part of the alkyl group may have one or more atoms or groups selected from group A),
R ¹⁰ is a hydrogen atom, one or more halogen atoms optionally may C1-C6 alkyl group which may have one or more halogen atoms optionally may C3-C6 alkenyl group which may have, have a one or more halogen atoms A C3-C6 alkynyl group which may have one or more, a C3-C7 cycloalkyl group which may have one or more halogen atoms, and a C3-C7 cycloalkyl group which may have one or more halogen atoms (C3-C7 cycloalkyl)- A (C1-C3 alkyl) group or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R ¹¹ is a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms, a C3-C7 cycloalkyl group which may have one or more halogen atoms, and a (C3-C7 cycloalkyl)-(C1- C3 alkyl) group or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R ¹² and R ¹³ each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R ¹⁴ represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or one or more halogen atoms Represents a C2-C6 alkoxycarbonyl group optionally having
n represents 0, 1, or 2;
m represents 0, 1, or 2;
p represents 0, 1, 2 or 3 (in the case where p represents 2 or 3, R ² may be the same or different from each other);
x represents 0 or 1,
y represents 0, 1, or 2.
Group A: C1-C6 alkyl group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms A good C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and A group consisting of halogen atoms.
Group B:

Group C:

Group D:

] (Hereinafter referred to as the present pyrimidinone compound),
A pest control composition (hereinafter referred to as the present invention composition) containing one or more compounds selected from the following group (a) or the following group (b) (hereinafter referred to as the present compound).
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, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7, hereinafter sometimes referred to as “insecticidal compound α”)

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2:
Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate ), Halfenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin, momfluorothrin, permethrin, phenothrin, praothrin prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), kappa-tefluthrin, tetramethrin (tetramethrin), tetramethi Flutrin (tetramethylfluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), benfluthrin (benfluthrin), flufenprox (flufenoprox), flumerin (flumethrin), framethrin (furamethrin), methfluthrin (metofluthrin), profluthrin and profluthrin (profluthrin) A group of sodium channel modulators consisting of (dimefluthrin).
Subgroup a-3:
GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide A group of agonistic chloride channel allosteric modulators.
Subgroup a-4:
Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
Subgroup a-5:
Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
Subgroup a-6:
A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
Subgroup a-7:
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of 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, bitertanol, bromuconazole, cyproconazole, difenoconazole, diiconazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole ), Simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine and triticonazole A group of sterol biosynthesis inhibitors.
Subgroup b-2:
Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
Subgroup b-3:
A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
Subgroup b-4:
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No. 141573-94-6, hereinafter 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 sometimes referred to as “bactericidal compound β2”), 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4- Yl) -1-methylpyrazole-4-carboxamide (CAS Registry Number 1383809-87-7, hereinafter sometimes 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 sometimes referred to as “bactericidal compound β4”) and N-cyclopropyl- 3- (Difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number 1255734-28-1, hereinafter referred to as “bactericidal compound β5”) A group of succinate dehydrogenase inhibitors.
Subgroup b-5:
It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam. A group of β-tubulin polymerization inhibitors.
Subgroup b-6:
Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride A group of multi-acting point contact active compounds consisting of
Subgroup b-7:
Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid A group of cellulose synthesis inhibitors.
Subgroup b-8:
MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin group.
Subgroup b-9:
A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.
[2]
The pest according to [1], wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (a) is 100: 1 to 1: 100 by weight. Control composition.
[3]
The pest according to [1], wherein the content ratio of the compound represented by the formula (1) to one or more compounds selected from the group (a) is 10: 1 to 1:10 by weight. Control composition.
[4]
The pest according to [1], wherein the weight ratio of the compound represented by the formula (1) to one or more compounds selected from the group (b) is 10,000: 1 to 1: 100. Control composition.
[5]
The pest according to [1], wherein the weight ratio of the compound represented by the formula (1) to one or more compounds selected from the group (b) is 1000: 1 to 1:10. Control composition.
[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, plant seed, bulb or soil for cultivating a plant.
[8]
Plant seeds or bulbs to which an effective amount of the pesticidal composition according to any one of [1] to [5] is attached.

According to the present invention, pests can be controlled.

The composition of the present invention contains the present pyrimidinone compound and the present compound.

Examples of substituents used in the description of the present specification will be described below.
The notation “may have one or more atoms or groups selected from group A” means that when it has two or more atoms or groups selected from group A, atoms selected from those groups ○ Alternatively, the groups may be the same as or different from each other.
The expression “which may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other.
The expression “having one or more halogen atoms”, when having two or more halogen atoms, may be the same as or different from each other.

“Heterocyclic group” means a group containing at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as a ring-constituting atom, an aromatic heterocyclic group and a non-aromatic group Represents a heterocyclic group.

Examples of the “aromatic heterocyclic group” include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 1-pyrrolyl. Groups, 5-membered aromatic heterocyclic groups such as 1-pyrazolyl group, 1-imidazolyl group, 1,2,4-triazol-1-yl group; and 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, etc. A 6-membered aromatic heterocyclic group bonded at the carbon atom.

Examples of the “non-aromatic heterocyclic group” include aziridin-1-yl group, azetidin-1-yl group, pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidin-1-yl group , Non-aromatic heterocycles such as tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, piperidin-1-yl group, morpholin-4-yl group, thiomorpholin-4-yl group, azepan-1-yl group Groups.

“5- or 6-membered heteroaryl” represents a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group.

Examples of the “C2-C10 haloalkyl group” include 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group , Heptafluoroisopropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,4,4,4-hexafluorobutyl group Etc.

Examples of the “C3-C10 haloalkenyl group” include 3,3-difluoro-2-propenyl group, 3,3-difluoro-2-propenyl group, 4,4-difluoro-3-butenyl group and the like.

Examples of the “C3-C10 haloalkynyl group” include 3-chloro-2-propynyl group, 3-fluoro-2-propynyl group, 4,4,4-trifluoro-2-butynyl group and the like.

“(C1-C5 alkyl) -O— (C2-C5 alkyl) group having one or more halogen atoms” means a group having one or more halogen atoms in a C1-C5 alkyl moiety and / or a C2-C5 alkyl moiety. And examples thereof include 2- (2,2,2-trifluoroethoxy) ethyl group and 1,1,1-trifluoro-3-methoxypropan-2-yl group.

“(C3-C5 alkenyl) -O— (C2-C5 alkyl) having one or more halogen atoms” means a group having one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. For example, 2- (3,3-difluoro-2-propenyloxy) ethyl group.

“(C3-C5 alkynyl) -O— (C2-C5 alkyl) group having one or more halogen atoms” means a group having one or more halogen atoms in the C3-C5 alkynyl moiety and / or C2-C5 alkyl moiety. For example, a 2- (4,4,4-trifluoro-2-butynyloxy) ethyl group.

“(C1-C5 alkyl) -S (O) _m — (C2-C5 alkyl) group having one or more halogen atoms” means one or more halogen atoms in the C1-C5 alkyl portion and / or the C2-C5 alkyl portion. Represents a group having an atom, and examples thereof include a 2- (trifluoromethylthio) ethyl group, a 2- (trifluoromethylsulfinyl) ethyl group, and a 2- (trifluoromethylsulfonyl) ethyl group.

“(C3-C5 alkenyl) -S (O) _m — (C2-C5 alkyl) group having one or more halogen atoms” means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, and examples thereof include a 2- (3,3-difluoro-2-propenylthio) ethyl group.

“(C3-C5 alkynyl) -S (O) _m — (C2-C5 alkyl) group having one or more halogen atoms” means one or more halogen atoms in the C3-C5 alkenyl moiety and / or C2-C5 alkyl moiety. Represents a group having an atom, for example, 2- (4,4,4-trifluoro-2-butynylthio) ethyl group.

"(C1-C5 alkyl) -C (O)-(C1-C5 alkyl) group having one or more halogen atoms" means any one C1-C5 alkyl moiety or both C1-C5 alkyl group moieties Represents a group having one or more halogen atoms, and examples thereof include a 3,3,3-trifluoro-2-oxopropyl group.

“(C1-C3 alkyl) -O— (C1-C3 alkyl) group optionally having one or more halogen atoms” refers to any one C1-C3 alkyl moiety or both C1-C3 alkyl A group having one or more halogen atoms in the group part is represented, and examples thereof include a methoxymethyl group, a trifluoromethoxymethyl group, a difluoro (methoxy) methyl group, and a difluoro (trifluoromethoxy) methyl group.

Examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, pentyl group, hexyl group, trifluoromethyl A C1-C6 alkyl group optionally having one or more halogen atoms such as a group, a trichloromethyl group, a 2,2,2-trifluoroethyl group and a pentafluoroethyl group;
It has one or more halogen atoms such as vinyl group, 1-propenyl group, 2-propenyl group, 1-methylvinyl group, 1-pentenyl group, 1-hexenyl group, 1,1-difluoroallyl group and pentafluoroallyl group. A C2-C6 alkenyl group which may optionally have one or more halogen atoms such as an ethynyl group, a propargyl group, a 1-hexynyl group and a 4,4,4-trifluoro-2-butynyl group. A C6 alkynyl group is mentioned.

Examples of the “phenyl group optionally having one or more atoms or groups selected from group A” include a phenyl group, a 2-fluorophenyl group, a 4-fluorophenyl group, a 2,3-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4- (trifluoromethyl) phenyl group, 4- (trifluoromethoxy) phenyl Groups, 4- (trifluoromethylsulfanyl) phenyl group, 4-cyanophenyl group, 4- (methylsulfinyl) phenyl group, and 4- (methylsulfonyl) phenyl group.

As "any five-membered aromatic heterocyclic group selected from group B (the 5-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)". For example, pyrrol-1-yl group, 2-chloropyrrol-1-yl group, pyrazol-1-yl group, 3- (trifluoromethyl) pyrazol-1-yl group, 4-chloroimidazol-1-yl group, 1,2,4-triazol-1-yl group, 3-methoxy-1,2,4-triazol-1-yl group, 3-methylthio-1,2,4-triazol-1-yl group, 1,2 , 3-Triazol-1-yl group, oxazol-2-yl group, thiazol-2-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-yl And 1,2,4-oxadiazol-3-yl And the like.

As “any 6-membered aromatic heterocyclic group selected from group C (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A)”. For example, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, 4-trifluoromethylpyridin-2-yl group, 2-chloropyridin-5-yl group, pyrimidin-2-yl Group, pyrazin-2-yl group, pyrimidin-4-yl group, pyridazin-3-yl group, pyrimidin-5-yl group, and pyridazin-4-yl group.

"Any 3-7 membered non-aromatic heterocyclic group selected from group D (the 3-7 membered non-aromatic heterocyclic group is one or more selected from the group consisting of a halogen atom and a C1-C6 alkyl group" The group may have an atom or a group ”as, for example, aziridin-1-yl group, azetidin-1-yl group, pyrrolidin-1-yl group, 3,3,4,4-tetrafluoropyrrolidine-1 -Yl group, piperidin-1-yl group, 4,4-dimethylpiperidin-1-yl group, azepan-1-yl group.

Examples of the “C3-C7 cycloalkyl group optionally having one or more halogen atoms” include a cyclopropyl group, a 2,2-difluorocyclopropan-1-yl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, A cycloheptyl group etc. are mentioned.

“(C3-C7 cycloalkyl)-(C1-C3 alkyl) group optionally having one or more halogen atoms” represents a group having one or more halogen atoms in the C3-C7 cycloalkyl moiety; Examples thereof include a cyclopropylmethyl group, a 2- (cyclopropyl) ethyl group, a (2,2-difluorocyclopropyl) methyl group, and a cyclopentylmethyl group.

Examples of the “phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A)” include, for example, a benzyl group, 2-fluoro Examples include benzyl group, 4-chlorobenzyl group, 4- (trifluoromethyl) benzyl group, 2- (4- (trifluoromethyl) phenyl) ethyl group and the like.

“(5- or 6-membered heteroaryl) C1-C6 alkyl group (the 5- or 6-membered heteroaryl) of the (5- or 6-membered heteroaryl) C1-C6 alkyl group has one or more atoms or groups selected from group A; For example, (1-methylpyrrol-3-yl) methyl group, (oxazol-2-yl) methyl group, (tetrahydrofuran-3-yl) methyl group, (tetrahydrofuran-2). 1 (5-membered heteroaryl) C1-C6 alkyl such as -yl) methyl group, 2- (1,2,4-triazol-1-yl) ethyl group, (2-chlorothiazol-5-yl) methyl group Group;
(Pyridin-2-yl) methyl group, (pyridin-4-yl) methyl group, (pyrimidin-2-yl) methyl group, (pyrimidin-4-yl) methyl group, 2- (2-chloropyridin-5- And (6-membered heteroaryl) C1-C6 alkyl groups such as yl) ethyl group and [2- (trifluoromethyl) pyridin-2-yl] methyl group.

“Halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the “C2-C6 alkoxycarbonyl group” include a methoxycarbonyl group and an ethoxycarbonyl group.

Examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include a trifluoromethoxy group and a 2,2,2-trifluoroethoxy group.

“C1-C3 alkyl) -S (O) _y — (C1-C3 alkyl) group optionally having one or more halogen atoms” means a C1-C3 alkyl moiety and / or a C1-C3 alkyl moiety Represents a group which may have one or more halogen atoms, for example, methylthiomethyl group, trifluoromethylthiomethyl group, methanesulfinylmethyl group, trifluoromethanesulfonylmethyl group, methanesulfonylmethyl group, 2- (methylthio) ethyl Group and ethylthiomethyl group.

The “C1-C6 fluoroalkyl group” represents a C1-C6 alkyl group having one or more fluorine atoms, and examples thereof include a fluoromethyl group, a trifluoromethyl group, and a 2,2,2-trifluoroethyl group. .

Examples of the pyrimidinone compound include the following compounds.

[Aspect 1] In this pyrimidinone compound, G is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, or a (C1-C5 alkyl) -O— (C2- C5 alkyl) group, or one or more with a halogen atom (C1-C5 alkyl) -S (O) _m - (a C2-C5 alkyl) group,
R ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ² is a C1-C6 alkyl group which may have one or more halogen atoms, and any 5-membered aromatic heterocyclic group selected from the group consisting of groups B-1 to B-4 (the 5 The membered aromatic heterocyclic group may have one or more halogen atoms), any non-aromatic heterocyclic group selected from the group consisting of groups D-1 to D-8 (provided that The non-aromatic heterocyclic group may have one or more halogen atoms), OR ⁷ , NR ⁸ R ⁹ , S (O) _y R ¹² ;
R ⁷ has a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, or one or more halogen atoms. And may be a C3-C6 alkynyl group,
R ⁸ is a hydrogen atom or a C1-C6 alkyl group,
R ⁹ is a hydrogen atom, a C1-C6 alkyl group, a (5-membered heteroaryl) C1-C6 alkyl group (the 5-membered heteroaryl part of the (5-membered heteroaryl) C1-C6 alkyl group is selected from group A 1 (It may have the above atoms or groups.)
p is 0 or 1;
A compound in which y is 0, 1 or 2.
[Aspect 2] A compound according to Aspect 1, wherein G is a C2-C10 haloalkyl group or a C3-C10 haloalkenyl group, and R ³ is a hydrogen atom.
[Aspect 3] A compound according to Aspect 1, wherein G is a C3-C6 alkyl group having 3 or more fluorine atoms, R ¹ is an ethyl group, and R ³ is a hydrogen atom.
[Aspect 4] In Aspect 1, G is a C2-C10 haloalkyl group or a C3-C10 haloalkenyl group,
R ¹ is a C1-C6 alkyl group, p is 0 or 1,
R ² is one or more halogen atoms optionally may C1-C6 alkyl group which may have one or more halogen atoms which may have a 1,2,4-triazol-1-yl group, 1 or more A pyrrolidin-1-yl group optionally having a halogen atom, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkyl optionally having one or more halogen atoms Sulfanyl group, C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, di (C1-C6 alkyl) amino group A compound which is a (thiazol-5-ylmethyl) amino group or an amino group which may have one or more halogen atoms.
[Aspect 5] A compound according to Aspect 1, wherein G is a C2-C6 haloalkyl group, a C3-C10 haloalkenyl group, or a C3-C10 haloalkynyl group, and R ³ is a hydrogen atom or a C1-C3 alkyl group.
[Aspect 6] In aspect 1, Q is an oxygen atom,
G is a C2-C6 haloalkyl, R ¹ is a C1-C6 alkyl group,
p is 1, R ² is a C1-C6 fluoroalkyl group,
A compound in which R ³ is a hydrogen atom.
[Aspect 7] A compound according to Aspects 1 to 6, wherein A ¹ is CH, A ² is CR ^3a , and A ³ is a nitrogen atom.
[Aspect 8] A compound according to Aspects 1 to 6, wherein A ¹ is CH, A ² is CR ^3a , R ^3a is a hydrogen atom or a C1-C3 alkyl group, and A ³ is a nitrogen atom.
[Aspect 9] A compound according to Aspects 1 to 6, wherein A ¹ is a nitrogen atom, A ² is CR ^3a , and A ³ is a nitrogen atom.
[Aspect 10] A compound according to Aspects 1 to 6, wherein A ¹ is a nitrogen atom, A ² is CR ^3a , R ^3a is a hydrogen atom or a C1-C3 alkyl group, and A ³ is a nitrogen atom.
[Aspect 11] A compound according to Aspects 1 to 6, wherein A ¹ is CH, A ² is a nitrogen atom, and A ³ is CR ^3b .
In [Mode 12] embodiments 1-6, A ¹ is CH, A ² is nitrogen atom, A ³ is CR ^3b, compounds R ^3b is a hydrogen atom or a C1-C3 alkyl group.
[Aspect 13] A compound according to Aspects 1 to 6, wherein A ¹ is a nitrogen atom, A ² is a nitrogen atom, and A ³ is CR ^3b .
[Aspect 14] A compound according to Aspects 1 to 6, wherein A ¹ is a nitrogen atom, A ² is a nitrogen atom, A ³ is CR ^3b , and R ^3b is a hydrogen atom or a C1-C3 alkyl group.

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

The present pyrimidinone compound and intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 18).

Manufacturing method 1
In the formula (1), Q is an oxygen atom and the present pyrimidinone compound (1b) in which n = 1 (hereinafter referred to as the present pyrimidinone compound (1b)), and in the formula (1), Q is an oxygen atom and n = The present pyrimidinone compound (1c) 2 (hereinafter referred to as the present pyrimidinone compound (1c)) is represented by the present pyrimidinone compound (1a) in which Q is an oxygen atom and n = 0 in the formula (1) (It is described as (1a).) And an oxidant.

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

First, a method for producing the pyrimidinone compound (1b) from the pyrimidinone compound (1a) will be described.
The reaction is usually performed in the presence of 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, the oxidizing agent is usually used in a proportion of 1 to 1.2 mol per 1 mol of the pyrimidinone compound (1a).
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 and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. The pyrimidinone compound (1b) can be isolated by drying and concentrating the organic layer.

Next, a method for producing the pyrimidinone compound (1c) from the pyrimidinone compound (1b) will be described.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for 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 at a ratio of 1 to 2 moles relative to 1 mole of the pyrimidinone compound (1b).
The reaction temperature is usually in the range of −20 to 120 ° 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 and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. The pyrimidinone compound (1c) can be isolated by drying and concentrating the organic layer.

Moreover, this pyrimidinone compound (1c) can be manufactured by one-step reaction (one pot) by making this pyrimidinone compound (1a) and an oxidizing agent react.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons.
Examples of the oxidizing agent used in the reaction include mCPBA.
For the reaction, the oxidizing agent is usually used at a ratio of 2 to 3 moles per 1 mole of the pyrimidinone compound (1a).
The reaction temperature is usually in the range of 0 to 120 ° 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 and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash. The pyrimidinone compound (1c) can be isolated by drying and concentrating the organic layer.

Manufacturing method 2
The pyrimidinone compound (1a) is a base composed of a compound represented by formula (M1) (hereinafter referred to as compound (M1)) and a compound represented by formula (R1) (hereinafter referred to as compound (R1)). It can manufacture by making it react in presence of.

[Wherein V represents a fluorine atom or a chlorine atom, and other symbols represent the same meaning as described above. ]
The reaction is usually performed in the presence of 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), dimethyl sulfoxide (hereinafter referred to as DMSO), and the like. (Hereinafter referred to as aprotic polar solvent).
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates), and alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides). .)
In the reaction, compound (R1) is usually used at a ratio of 1 to 10 moles and base is usually used at a ratio of 1 to 10 moles relative to 1 mole of compound (M1).
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 pyrimidinone compound (1a) 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 3
The pyrimidinone compound represented by the formula (1z) (hereinafter referred to as the present pyrimidinone compound (1z)) is represented by the compound represented by the formula (M2) (hereinafter referred to as the compound (M2)) and the formula (R2). The compound shown below (hereinafter referred to as compound (R2)) can be produced by reacting in the presence of a base.

[Wherein, V ² represents a chlorine atom, a bromine atom, an iodine atom, or a C1-C10 perfluoroalkanesulfonyloxy group, and other symbols have the same meanings as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons and aprotic polar solvents.
Examples of the base used in the reaction include organic bases such as triethylamine, diisopropylpyrroleamine, pyridine, 4-dimethylaminopyridine (hereinafter referred to as organic bases), alkali metal hydrides, or alkali metal carbonates. Examples include salts.
For the reaction, the compound (R2) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 0.1 to 5 mol with respect to 1 mol of the compound (M2).
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 pyrimidinone compound (1) 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 4
Compound (M1) can be produced by reacting a compound represented by formula (M3) (hereinafter referred to as compound (M3)) with compound (R2) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
In this reaction, compound (M1) can be produced according to the reaction described in Production Method 3 by using compound (M3) instead of compound (M2).

Manufacturing method 5
Compound (M2b) where n = 1 in compound (M2) (hereinafter referred to as compound (M2b)) and Compound (M2c) where n = 2 in compound (M2) (hereinafter referred to as compound (M2c)) .) Can be produced by reacting a compound (M2a) in which n = 0 in the compound (M2) (hereinafter referred to as compound (M2a)) with an oxidizing agent.

[Wherein the symbols have the same meaning as in formula (1). ]
In this reaction, the compound (M2a) is used in place of the pyrimidinone compound (1a), and the compound (M2b) is used in place of the pyrimidinone compound (1b). Thus, the compound ( M2b) and compound (M2c) can be prepared.

Manufacturing method 6
Compound (M2a) can be produced by reacting compound (M3) with compound (R1) in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
In this reaction, compound (M2a) can be produced according to the method described in production method 2, using compound (M3) instead of compound (M1).

Manufacturing method 7
Compound (M3) can be produced, for example, according to the following method.

[Wherein, R represents a C1-C3 alkyl group, M represents —B (OH) ₂ , 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, —SnBu ₃ , -ZnCl, -MgCl, or -MgBr, and other symbols have the same meanings as described above. ]

First, a method for producing a compound represented by the formula (M9) (hereinafter referred to as compound (M9)) will be described.
The compound (M9) includes a compound represented by the formula (M10) (hereinafter referred to as the compound (M10)) and a compound represented by the formula (M11) (hereinafter referred to as the compound (M11)) as a metal catalyst. It can manufacture by making it react in presence of.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as ethylene glycol dimethyl ether (hereinafter referred to as DME) and tetrahydrofuran (hereinafter referred to as THF) (hereinafter referred to as ethers), and aromatics such as toluene and xylene. Group hydrocarbons (hereinafter referred to as aromatic hydrocarbons), aprotic polar solvents, water, and mixtures thereof.
Examples of the metal catalyst used in the reaction include tetrakistriphenylphosphine palladium (0), 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride, tris (dibenzylideneacetone) dipalladium (0), acetic acid. Palladium catalysts such as palladium (II), nickel catalysts such as bis (cyclooctadiene) nickel (0), nickel (II) chloride, copper catalysts such as copper (I) iodide, copper (I) chloride, etc. .
In the reaction, a ligand, a base and an inorganic halide may be added as necessary.
Examples of the ligand used in the reaction include triphenylphosphine, xanthophos, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 1,1′-bis (diphenylphosphino) ferrocene, 2- Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 1,2-bis (diphenylphosphino) ethane, 2,2′-bipyridine 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline and the like.
Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.
Examples of the inorganic halide used in the reaction include alkali metal fluorine salts such as potassium fluoride and sodium fluoride, and alkali metal chlorine salts such as lithium chloride and sodium chloride.
In the reaction, with respect to 1 mol of the compound (M10), the compound (M11) is usually in a proportion of 1 to 10 mol, the metal catalyst is usually in a proportion of 0.01 to 0.5 mol, and the ligand is usually in a proportion of 0.00. A proportion of 01 to 1 mol, a base of usually 0.1 to 5 mol, and an inorganic halide of usually 0.1 to 5 mol are used.
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, the compound (M9) 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.

Then, it describes about the method of manufacturing a compound (M3) from a compound (M9).
Compound (M3) can be produced by reacting compound (M9) in the presence of an acid.
The reaction is performed in the presence of a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, aromatic hydrocarbons, alcohols such as methanol and ethanol (hereinafter referred to as alcohols), acetic acid, water, and mixtures thereof.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid.
In the reaction, an acid is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M9). Mineral acids can also be used as a solvent.
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, add water to the reaction mixture, extract with an organic solvent, and concentrate the organic layer; add a solvent to the reaction mixture and collect the resulting solid by filtration; or filter the solid produced in the reaction mixture The compound (M3) can be isolated by collecting by

Manufacturing method 8
Compound (M2a) 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 formula (M12) (hereinafter referred to as compound (M12)) from compound (M9) will be described.
Compound (M12) can be produced by reacting compound (M9) with compound (R1) in the presence of a base.
In this reaction, compound (M12) can be used in place of compound (M1), and compound (M12) can be produced according to the method described in Production Method 2.

Then, it describes about the method of manufacturing a compound (M2a) from a compound (M12).
Compound (M2a) can be produced by reacting compound (M12) in the presence of an acid.
In this reaction, compound (M2a) can be produced according to the method described in production method 7 using compound (M12) instead of compound (M9).

Manufacturing method 9
In compound (M3), compound (M3-1) in which A ² is CR ^3a and A ³ is a nitrogen atom (hereinafter referred to as compound (M3-1)) can be produced, for example, according to the following method. it can.

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

First, a method for producing a compound represented by the formula (M5) (hereinafter referred to as compound (M5)) will be described.
Compound (M5) can be produced by reacting a compound represented by formula (M6) (hereinafter referred to as compound (M6)) with a carbonate in the presence of a base.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers, aliphatic halogenated hydrocarbons, and aprotic polar solvents.
Examples of the base used in the reaction include alkali metal hydrides, or alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide (hereinafter referred to as alkali metal alkoxides).
Examples of the carbonate ester used in the reaction include dimethyl carbonate, diethyl carbonate, and dipropyl carbonate.
In the reaction, with respect to 1 mol of the compound (M6), the ester carbonate is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0.1 to 5 mol. Carbonic acid esters can also be used as a solvent.
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, the compound (M5) 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.

In addition, a method for producing the compound (M5) from the compound represented by the formula (M7) (hereinafter referred to as the compound (M7)) will be described.
Compound (M5) is obtained by reacting compound (M7) with a compound represented by the formula (R3) (hereinafter referred to as compound (R3)) in the presence of magnesium chloride and a base, and then reacting with an acidic aqueous solution. It can be produced by reacting.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers and aprotic polar solvents.
Examples of the base used in the reaction include organic bases.
Examples of the acidic aqueous solution used for the reaction include aqueous solutions of mineral acids such as hydrochloric acid and sulfuric acid.
In the reaction, with respect to 1 mole of the compound (M7), the compound (R3) is usually 1 to 10 moles, the magnesium chloride is usually 1 to 10 moles, the base is usually 0.1 to 10 moles, As the acidic aqueous solution, 1N to 12N acidic aqueous solution is used at a ratio of 1 to 100 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, the compound (M5) 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.

Then, it describes about the method of manufacturing the compound (henceforth a compound (M4)) represented by a formula (M4) from a compound (M5).
Compound (M4) can be produced by reacting compound (M5) with ammonium acetate.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include an aprotic polar solvent.
In the reaction, ammonium acetate is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M5).
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, the compound (M4) 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.

Subsequently, a method for producing the compound (M3-1) from the compound (M4) will be described.
Compound (M3-1) can be produced by reacting compound (M4) with a compound represented by formula (R6) (hereinafter referred to as compound (R6)) in the presence of a base.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include alcohols, ethers, and aprotic polar solvents.
Examples of the base used in the reaction include alkali metal hydrides and alkali metal alkoxides.
In the reaction, with respect to 1 mol of compound (M4), compound (R6) 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 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (M3-1) can be isolated by post-treatment such as addition of water to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer.

Manufacturing method 10
The compound represented by the formula (M2a-1) (hereinafter referred to as the compound (M2a-1)) can be produced, for example, according to the following method.

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

As the compound (M14), a compound represented by the formula (M16) (hereinafter referred to as the compound (M16)) is used in place of the compound (M7), or a compound (M15) is used instead of the compound (M6). The compound can be produced according to the method described in Production Method 9 (hereinafter referred to as Compound (M15)).
For the compound represented by the formula (M13) (hereinafter referred to as the compound (M13)), a compound represented by the formula (M14) (hereinafter referred to as the compound (M14)) was used instead of the compound (M5). It can be produced according to the method described in production method 9.
Compound (M2a-1) can be produced according to the method described in production method 9, using compound (M13) instead of compound (M4).

Manufacturing method 11
The compound represented by the formula (M2a-2) (hereinafter referred to as the compound (M2a-2)) 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 (M21) (hereinafter referred to as the compound (M21)) will be described.
Compound (M21) can be produced according to the method described in Production Method 9, using a compound represented by the formula (R4) (hereinafter, referred to as compound (R4)) instead of carbonate ester.

Next, a method for producing a compound represented by the formula (M3-2) (hereinafter referred to as the compound (M3-2)) will be described.
Compound (M3-2) can be produced by reacting compound (M21) with urea.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include alcohols, aprotic polar solvents, acetic acid, water, and mixtures thereof.
In the reaction, urea is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (M21).
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, the compound (M3-2) 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.

Next, a method for producing a compound represented by the formula (M22) (hereinafter referred to as compound (M22)) will be described.
Compound (M22) can be produced by reacting compound (M6) with a compound represented by formula (R5) (hereinafter referred to as compound (R5)).
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include an aprotic polar solvent and a mixture thereof.
In the reaction, compound (R5) is usually used at a ratio of 1 to 100 mol per 1 mol of compound (M6). In addition, compound (R5) can also be used as a solvent.
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, the compound (M22) 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.

Subsequently, a method for producing the compound (M3-2) from the compound (22) will be described.
Compound (M3-2) can be produced by reacting compound (22) with urea in the presence of a base.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include alcohols and aprotic polar solvents.
Examples of the base used for the reaction include alkali metal alkoxides.
In the reaction, with respect to 1 mole of the compound (M22), urea is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 5 moles.
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, the compound (M3-2) 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.

Next, a method for producing compound (M2a-2) will be described.
Compound (M2a-2) can be produced by reacting compound (M3-2) with compound (R1) in the presence of a base.
In this reaction, compound (M2a-2) can be produced according to the method described in Production Method 2 by using compound (M3-2) instead of compound (M1).

Production method 12
Compound (M2a-2) can be produced, for example, according to the following method.

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

These reactions can be carried out according to the method described in Production Method 11.

Production method 13
The present pyrimidinone compound represented by formula (1e) (hereinafter referred to as the present pyrimidinone compound (1e)) and the present pyrimidinone compound represented by formula (1d) (hereinafter referred to as the present pyrimidinone compound (1d)) and formula It can be produced by reacting a compound represented by (R16) (hereinafter referred to as compound (R16)) in the presence of a base.

[Wherein, X ² represents a fluorine atom, a chlorine atom, or S (O) ₂ R ¹ , and other symbols have the same meaning as described above. ]
Examples of the solvent used in the reaction include alcohols and aprotic polar solvents.
Examples of the base used for the reaction include alkali metal hydrides.
In the reaction, with respect to 1 mole of the pyrimidinone compound (1d), the compound (R16) 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 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the pyrimidinone compound (1e) 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 14
In the formula (1), the pyrimidinone compound (hereinafter referred to as the present pyrimidinone compound (1f)) in which Q is an oxygen atom, p is 1, and R ² is NR ⁵ R ⁶ is referred to as the present pyrimidinone compound ( It can be produced by reacting 1d) with a compound represented by the formula (R15) (hereinafter referred to as compound (R15)).

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers, aprotic polar solvents, water, and mixtures thereof.
This reaction can also be performed by adding a base as necessary.
Examples of the base used for the reaction include alkali metal carbonates, alkali metal hydrides, organic bases and the like.
In the reaction, with respect to 1 mole of the pyrimidinone compound (1d), the compound (R15) 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 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the pyrimidinone compound (1f) 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
In the formula (1), Q is an oxygen atom, p is 1, and R ² is SR ⁵ (hereinafter referred to as the present pyrimidinone compound (1g)), Q is an oxygen atom, The pyrimidinone compound (hereinafter referred to as the present pyrimidinone compound (1h)) in which p is 1 and R ² is S (O) R ⁸ , and Q is an oxygen atom, p is 1, R ² This pyrimidinone compound (hereinafter referred to as the present pyrimidinone compound (1i)) in which is S (O) ₂ R ⁸ can be produced, for example, according to the following method.

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

First, it describes about the method of manufacturing this pyrimidinone compound (1g).
The pyrimidinone compound (1g) can be produced by reacting the pyrimidinone compound (1d) with a compound represented by the formula (R18) (hereinafter referred to as compound (R18)) in the presence of a base. it can.
In this reaction, this pyrimidinone compound (1 g) can be produced according to the method described in Production Method 13 by using compound (R18) instead of compound (R16).

Then, it describes about the method of manufacturing this pyrimidinone compound (1h).
This pyrimidinone compound (1h) can be manufactured by making this pyrimidinone compound (1g) and an oxidizing agent react.
In this reaction, compound (1h) can be produced according to the method described in production method 1 by using compound (1g) instead of compound (1a).

Then, it describes about the method of manufacturing this pyrimidinone compound (1i).
The pyrimidinone compound (1i) can be produced by reacting the pyrimidinone compound (1h) with an oxidizing agent.
In this reaction, compound (1i) can be produced according to the method described in production method 1 by using compound (1h) instead of compound (1b).

Production method 16
The present pyrimidinone compound represented by the formula (1y) (hereinafter referred to as the present pyrimidinone compound (1y)) is sulfided with the present pyrimidinone compound represented by the formula (1z) (hereinafter referred to as the present pyrimidinone compound (1z)). It can manufacture by making an agent react.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, and aliphatic halogenated hydrocarbons.
Examples of the sulfurizing agent used in the reaction include 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphatan-2,4-disulfide.
In the reaction, the sulfurizing agent is usually used in a ratio of 1 to 10 mol per 1 mol of the pyrimidinone compound (1z).
The reaction temperature is usually in the range of −20 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the pyrimidinone compound (1y) 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 17
This pyrimidinone compound represented by the formula (1L) (hereinafter referred to as the present pyrimidinone compound (1L)) is composed of the present pyrimidinone compound (1d) and a compound represented by the formula (R28) (hereinafter referred to as the compound (R28)). .) In the presence of a base.

[Wherein, B ¹ and B ² each independently represent a nitrogen atom or CH, R ¹¹ represents a hydrogen atom, or one atom or group selected from group A, and the other symbols have the same meaning as described above. To express. ]
In this reaction, compound (R28) can be used instead of compound (R16), and this pyrimidinone compound (1L) can be produced according to the method described in Production Method 13.

Production method 18
This pyrimidinone compound represented by the formula (1m) (hereinafter referred to as the present pyrimidinone compound (1m)) is composed of the present pyrimidinone compound (1d) and a compound represented by the formula (R29) (hereinafter referred to as the compound (R29)). .) Can be made to react.

[Wherein t represents an integer of 0 to 4, and other symbols have the same meaning as described above. ]
In this reaction, compound (R29) can be used instead of compound (R15), and this pyrimidinone compound (1m) can be produced according to the method described in Production Method 14.

Next, specific examples of the pyrimidinone compound are shown below. In [Table 10] and [Table 12], PI represents a piperidin-1-yl group, PY represents a pyrrolidin-1-yl group, MO represents a morpholin-4-yl group, and TH represents a thiomorpholine-4 -Represents an yl group.

Formula (1-5)

Wherein R ³ and R ^3a are hydrogen atoms, R ²¹ , R ²² and R ²³ are hydrogen atoms, and R ¹ , G and n are the present pyrimidinones according to [Table 1] to [Table 4] Compound (hereinafter referred to as compound group SX1).
In the formula (1-5), R ³ and R ^3a are hydrogen atoms, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, and R ¹ , G, and n are [Tables] 1] to [Table 4] The pyrimidinone compounds (hereinafter referred to as compound group SX2).
In formula (1-5), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is CH ₃ , and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX3).
In formula (1-5), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is CH ₃ , R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX4).
In Formula (1-5), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is a fluorine atom, and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX5).
In formula (1-5), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is a fluorine atom, R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX6).
In Formula (1-5), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is a chlorine atom, and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX7).
In formula (1-5), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is a chlorine atom, R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX8).
In Formula (1-5), R ^3a is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ³ is CH ₃ , and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX9).
In the formula (1-5), R ^3a is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ³ is CH ₃ , R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX10).

In the formula (1-5), R ³ and R ^3a are hydrogen atoms, and R ¹ , G, n, R ²¹ , R ²² , and R ²³ are combinations shown in [Table 5] to [Table 13]. A certain pyrimidinone compound (hereinafter referred to as compound group SX11).

[Table 1]

[Table 2]

[Table 3]

[Table 4]

Formula (1-6)

Wherein R ³ and R ^3a are hydrogen atoms, R ²¹ , R ²² and R ²³ are hydrogen atoms, and R ¹ , G and n are the present pyrimidinones according to [Table 1] to [Table 4] Compound (hereinafter referred to as compound group SX12).
In the formula (1-6), R ³ and R ^3a are hydrogen atoms, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, and R ¹ , G, and n are [Table 1] to [Table 4] The pyrimidinone compounds (hereinafter referred to as compound group SX13).
In Formula (1-6), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is CH ₃ , and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX14).
In the formula (1-6), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is CH ₃ , R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX15).
In the formula (1-6), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is a fluorine atom, and R ¹ , G, and n are [Table 1] The pyrimidinone compounds described in [Table 4] (hereinafter referred to as compound group SX16).
In formula (1-6), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is a fluorine atom, R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX17).
In Formula (1-6), R ³ is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ^3a is a chlorine atom, and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX18).
In the formula (1-6), R ³ is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ^3a is a chlorine atom, R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX19).
In Formula (1-6), R ^3a is a hydrogen atom, R ²¹ , R ²² , and R ²³ are hydrogen atoms, R ³ is CH ₃ , and R ¹ , G, and n are [Table 1 ] To [Table 4], the pyrimidinone compounds (hereinafter referred to as compound group SX20).
In the formula (1-6), R ^3a is a hydrogen atom, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, R ³ is CH ₃ , R ¹ , G, And n is the pyrimidinone compound according to [Table 1] to [Table 4] (hereinafter referred to as compound group SX21).

In the formula (1-6), R ³ and R ^3a are hydrogen atoms, and R ¹ , G, n, R ²¹ , R ²² , and R ²³ are combinations shown in [Table 5] to [Table 13]. A certain pyrimidinone compound (hereinafter referred to as compound group SX22).

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

Formula (1-7)

R ³ and R ^3b are hydrogen atoms, R ²¹ , R ²² , and R ²³ are hydrogen atoms, and R ¹ , G, and n are the combinations described in [Table 1] to [Table 4] A certain pyrimidinone compound (hereinafter referred to as compound group SX23).
In Formula (1-7), R ³ and R ^3b are hydrogen atoms, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, and R ¹ , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX24) which are combinations described in Table 1] to [Table 4].
In the formula (1-7), R ³ and R ^3b are hydrogen atoms, and R ¹ , G, n, R ²¹ , R ²² , and R ²³ are combinations shown in [Table 5] to [Table 13]. A certain pyrimidinone compound (hereinafter referred to as compound group SX25).

Formula (1-8)

R ³ and R ^3b are hydrogen atoms, R ²¹ , R ²² , and R ²³ are hydrogen atoms, and R ¹ , G, and n are the combinations described in [Table 1] to [Table 4] A certain pyrimidinone compound (hereinafter referred to as compound group SX26).
In Formula (1-8), R ³ and R ^3b are hydrogen atoms, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, and R ¹ , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX27) which are combinations described in Table 1] to [Table 4].
In the formula (1-8), R ³ and R ^3b are hydrogen atoms, and R ¹ , G, n, R ²¹ , R ²² , and R ²³ are combinations shown in [Table 5] to [Table 13]. A certain pyrimidinone compound (hereinafter referred to as compound group SX28).

Formula (1-9)

R ³ and R ^3b are hydrogen atoms, R ²¹ , R ²² , and R ²³ are hydrogen atoms, and R ¹ , G, and n are the combinations described in [Table 1] to [Table 4] A certain pyrimidinone compound (hereinafter referred to as compound group SX29).
In the formula (1-9), R ³ and R ^3b are hydrogen atoms, R ²¹ and R ²³ are hydrogen atoms, R ²² is a trifluoromethyl group, and R ¹ , G, and n are [ The pyrimidinone compounds (hereinafter referred to as compound group SX30) which are combinations described in Table 1] to [Table 4].
In the formula (1-9), R ³ and R ^3b are hydrogen atoms, and R ¹ , G, n, R ²¹ , R ²² , and R ²³ are combinations shown in [Table 5] to [Table 13]. A certain pyrimidinone compound (hereinafter referred to as compound group SX31).

Examples of the compound of group (a) include compounds of 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, flupyrifurone, flupyradifurone ), Dichloromesothiaz (dicloromezotiaz) and a compound represented by the following formula (CAS registration number 1689566-03-7)

A group of competitive modulators of nicotinic acetylcholine receptors.
Subgroup a-2:
Acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta beta-cyfluthrin), cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, betacypermethrin ( beta-cypermethrin), theta-cypermethrin, theta-cypermethrin, sigma-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esf Enfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate ), Halfenprox, heptafluthrin, imiprothrin, kadethrin, meperfluthrin, momfluorothrin, permethrin, phenothrin, praothrin prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), kappa-tefluthrin, tetramethrin (tetramethrin), tetramethi Flutrin (tetramethylfluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), benfluthrin (benfluthrin), flufenprox (flufenoprox), flumerin (flumethrin), framethrin (furamethrin), methfluthrin (metofluthrin), profluthrin and profluthrin (profluthrin) A group of sodium channel modulators consisting of (dimefluthrin).
Subgroup a-3:
GABAergic chloride channel blocker consisting of ethiprole, fipronil and flufiprole, and GABA consisting of afoxalaner, fluralaner, broflanilide and fluxametamide A group of agonistic chloride channel allosteric modulators.
Subgroup a-4:
Group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, tetraniliprole and cyhalodiamide .
Subgroup a-5:
Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbofuran Fan (carbosulfan), ethiofencarb (fthiobucarb), fenobucarb (BPMC), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb: MIPC), methiocarb (methiocarb), methomyl (methomyl), metolcarb (MTMC) , Oxamyl, pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylica Bed (xylylcarb: MPMC) consists, the group of carbamates acetylcholinesterase (AChE) inhibitors.
Subgroup a-6:
A group of nematicidal active compounds consisting of abamectin, fluensulfone, tioxazafen, and fluazaindolizine.
Subgroup a-7:
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium, Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Pasturiatransurie, Pasturiapass A group of microbial materials consisting of Pasteuria usgae, Verticillium chlamydosporium and Harpin protein.

As used in the present invention, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, fluradifurone, fluradifurone , Triflumezopyrim, acrinathrin, allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioresmethrin, cycloresin, prothrin (Cyfluthrin), beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, Permethrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, sigma-cypermethrin , Cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate , Flumethrin, fluvalinate, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, kadethrin, meperf Luthrin (meperfluthrin), monfluorothrin (momfluorothrin), permethrin (phenmethrin), praothrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen, tefluthrin (tefluthrin) (Kappa-tefluthrin), tetramethrin, tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, flamethrin furamethrin), methofluthrin, profluthrin, dimefluthrin, ethiprole, fipronil, furfiprole, Lorantraniliprole, cyantraniliprole, cycloniliprole, flubendiamide, cyhalodiamide, alaniccarb, aldicarb, bendiocarb , Benfuracarb, butocarboxim, butoxycarboxim, carbaryl (NAC), carbofuran, carbosulfan, ethiofencarb, fenobucarb (BPMC) , Formetanate, furathiocarb, isoprocarb (MIPC), methiocarb, metomyl, metolcarb (MTMC), oxamyl, Pirimicarb, propoxur (PHC), thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb (MPMC), abamectin and fluenesulfone (Fluensulfone) is a known compound, for example, “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), tetraniliprolol (CAS registration number: 1229654-66-3), floxamethamide (CAS registration number: 928783-29-3, afoxoranel) used in the present invention (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 all known compounds, such as International Publication No. 2011/017342, International Publication No. 2010/066952, International Publication No. 2007/0269965, International Publication No. 2007/079162, International Publication No. 2005/085216, International Publication No. 2010/01 714 No., WO 2010/129500, WO 2006/114400, and can be produced respectively by the method described in WO 2012/029672.
Mycorrhiza Fungi, Arthrobotrys dactyloides, Bacillus thuringiensis, Bacillus firmus, Bacillus megaterium used in the present invention, Bacillus amyloliquefaciens, Hirsutella rhossiliensis, Hirsutella minnesotensis, Monacrosporium phymatopagus, Monacrosporium phymatopagus, Pasteuria e (Pasteuria penetrans), Pasturia usgae, Verticillium chlamydosporium and Harpin protein are all public A microbial materials, obtained from commercially available preparations or obtained by production using a known method.

Examples of the compound of the group (b) include compounds of subgroups b-1, b-2, b-3, b-4, b-5, b-6, b-7, b-8 and b-9 below. Is mentioned.
Subgroup b-1:
Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diiconazole, diniconazole-M, epiconconazole, ethaconazole (Etaconazole), fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole, imazaril ( imazalil), imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazole, o Spoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox, pyrisoxazole ), Simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine and triticonazole A group of sterol biosynthesis inhibitors.
Subgroup b-2:
Azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, fenaminstrobin, full Phenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metinominostrobin, orysastrobin, picoxystrobin , Pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, triazopyricarb Consisting de (cyazofamid) and amisulbrom (amisulbrom), the group of Qo inhibitors (Quinone outside inhibitors).
Subgroup b-3:
A group of RNA polymerase I inhibitors consisting of benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl and ofurace .
Subgroup b-4:
Benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad ), Furametpyr, isofetamid, isoprazam, mepronil, oxycarboxin, penthiopyrad, penflufen, sedaxane, thifluzamide, thifluamide (Pyraziflumid), pydiflumetofen (CAS registration number 1228284-64-7), 3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4- Carboxamide (CAS registration No. 141573-94-6), 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole-4-carboxamide (CAS Registry Number 1352994-67-) 2), 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7), 3- Difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS Registry Number 1513466-73-3) and N-cyclo Propyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS Registry Number 1255734-28-1) Ranaru, the group of succinate dehydrogenase inhibitors.
Subgroup b-5:
It consists of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide and ethaboxam. A group of β-tubulin polymerization inhibitors.
Subgroup b-6:
Ferbam, mancozeb, manneb, maneb, metiram, propineb, thiram, zineb, ziram, captan, captafol ), Folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine, dithianon, chinomethionate or quinomethionate fluoride A group of multi-acting point contact active compounds consisting of
Subgroup b-7:
Dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthivalicarb-isopropyl, iprovalicarb, valifenalate and mandipropamid A group of cellulose synthesis inhibitors.
Subgroup b-8:
MAP (mitogen-activated protein) / histidine kinase inhibitor in osmotic signal transduction consisting of fenpiclonil, fludioxonil, chlozolinate, iprodione, procymidone and vinclozolin group.
Subgroup b-9:
A group of other fungicides consisting of tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide and silthiofam.

Azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole M, diniconazole-M, epoxico, used in the present invention Epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, quinconazole, flusilazole, flutriafol, hexaconazole (Hexaconazole), imazalil, imibenconazole, ipconazole, metconazole, microbutanil, nuarimol, oxpoconazo Oxpoconazole, oxpoconazole fumarate, pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole, pyrifenox ( pyrifenox, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine, triforine Ticononazole, azoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone (fe namidone, fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metomominostrobin, orizastrobin (Orysastrobin), picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, pyribencarb, triclopyricarb (Triclopyricarb), cyazofamid, amisulbrom, benalaxyl, benalaxyl M, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxazi Oxadixyl, ofurace, benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil (Flutolanil), fluxapyroxad, furametpyr, isofetamid, isopyrazam, mepronil, oxycarboxin, penthiopyrad, penflufen, penflufen, penflufen (Sedaxane), thifluzamide, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, Etofencarb, diexofencarb, zoxamide, ethaboxam, ferbam, mancozeb, maneb, maneb, metiram, propineb, thiram, zineb ), Ziram, captan, captafol, folpet, chlorothalonil, tolylfluanid, guazatine, iminoctadine, anilazine , Dithianon, chinomethionat or quinomethionate, fluoroimide, dimethomorph, flumorph, pyrimorph, benchthiavalicarb, benchthiavalicarb-isopropyl ), Iprovalicarb, valifenalate, mandipropamid, fenpiclonil, fludioxonil, clozolinate, iprodione, procymidone, vincrozoline, vinclozoline, vinclozoline Tolclofos-methyl, oxathiapiproline, picarbutrazox, fluopicolide, and silthiofam are all “MeisterPro Crop Protection Handbook Vol. 100 (2014) "and the like. These compounds can be obtained from commercially available preparations or produced by known methods.
Pyraziflumid used in the present invention is a known compound and can be produced, for example, by the method described in International Publication No. 2007/072999.
Pidiflumetofen used in the present invention is a known compound and can be produced, for example, by the method described in WO2010 / 063700.
3-difluoromethyl-1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide (CAS registration number 141573-94-6), 3-difluoro used in the present invention Methyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4-yl] pyrazole-4-carboxamide (CAS Registry Number 1352994-67-2) is a known compound, For example, it can be produced by the method described in International Publication No. 2011/162397, respectively.
3-Difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole-4-carboxamide (CAS registration number 1383809-87-7) used in the present invention 3-difluoromethyl-N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (CAS Registry Number 1513466-73-3) is All are known compounds and can be produced, for example, by the methods described in International Publication No. 2012/084812.
N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS registration number) used in the present invention 1255734-28-1) is a known compound and can be produced, for example, by the method described in International Publication No. 2013/160387.

Below, the example of the combination of this pyrimidinone compound and this compound in this invention composition is described. The abbreviation for SX means “any one of the present pyrimidinone compounds selected from the compound group SX1 to SX31”.
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 minnesota Crospodium fimatopagum + SX, Pasteuria nisawae + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Verticillium kuramidosporia + SX, Harpin protein + 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 pyrimidinone compound and the present compound, but usually the present pyrimidinone compound and the present compound are mixed with an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier. If necessary, add surfactants and other formulation adjuvants, emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, 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 amount of the pyrimidinone 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.

Examples of other adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-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 formulation is obtained by kneading the pyrimidinone 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, if necessary. 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, for example, animal collars, animal ear tags, sheet preparations, attraction strings, 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 chili powder, anti-fouling agents by children and pets, cheese flavor, onion flavor, peanut oil and other pest-attracting flavors.

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

The pest control method of the present invention is performed by applying an effective amount of the composition of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.). .

Examples of the application method of the composition of the present invention include application to plants, application to soil where plants are cultivated, application to plant seeds or bulbs. Examples of application to plants include application to plant foliage, flower vases, seedlings or ears. Examples of the application to soil for cultivating plants include application to soil before planting or after planting. Examples of application to plant seeds or bulbs include seed disinfection, seed soaking, and seed coating. In addition, the pyrimidinone compound and the compound may be applied separately. Before and after planting seeds or bulbs to which either the pyrimidinone compound or the compound is attached to the soil, the remaining one is applied to the soil. Also good.

Specific examples of application to plant stems and leaves, flower vases, seedlings or ears include application methods applied to the surface of plants such as foliage spraying, trunk spraying, etc., and before flowering, during flowering, after flowering. Examples include a method of spraying the entire vase or the whole plant at the flowering time, and a method of spraying the head or the whole plant at the heading time for cereals.

In addition, the method of applying to the soil before or after planting is, for example, by applying the composition of the present invention to the rhizosphere of a crop to be protected from damage such as feeding by pests. It is a method for controlling pests directly, or a method for controlling pests such as feeding plants by osmotically transferring the present pyrimidinone compound and the present compound from the root to the inside of the plant body.
Specifically, for example, planting treatment (planting hole spraying, planting hole treatment soil mixing), plant source processing (stock source spraying, strain source soil mixing, strain source irrigation, late seedling stage plant source processing), planting groove processing (Groove spraying, grooving soil admixture), cropping treatment (growing sprinkling, cropping soil blending, growing season cropping spraying), sowing cropping treatment (sowing cropping spraying, sowing cropping soil blending) , Whole surface treatment (overall soil application, whole surface soil admixture), side strip treatment, water surface treatment (water surface application, water surface application after submergence), other soil application treatment (growth season foliar leaf surface application, under the crown or around the trunk, Soil surface spraying, soil surface mixing, sowing hole spraying, buttocks ground surface spraying, inter-strain spraying), and other irrigation treatments (soil irrigation, seedling irrigation, chemical solution injection treatment, local irrigation, chemical drip irrigation, chemical ligation), Nursery box processing (nursery box spraying, seedling box irrigation, seedling box chemical solution watering), seedling tray processing ( Seedling tray spraying, seedling tray irrigation, seedling tray chemical solution flooding), seedling treatment (seedbed spraying, seedbed irrigation, water seedling substitute seedbed spraying, seedling soaking), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, seeding) Application before soil covering, after soil covering after seeding, mixing with soil covering) and other treatments (mixing soil, mixing, topsoil mixing, rain soil mixing, planting position treatment, granule inflorescence spraying, paste fertilizer mixing).

In the present invention, the plant seed means plant seed in a state before being sown in the soil or the culture medium, and the bulb is a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes, stem fragments, seed pods and tuberous roots. The method of applying the composition of the present invention to plant seeds or bulbs is, for example, a method of controlling pests by applying the composition of the present invention directly to plant seeds or bulbs to be protected from damage such as feeding by pests. A method for controlling pests that feed on seeds, etc. by applying the composition of the present invention in the vicinity of plant seeds, bulbs, etc .; or It is a method for controlling pests such as feeding plants by osmotic transfer. Specifically, for example, spraying treatment, smearing treatment, dipping treatment, impregnation treatment, coating treatment, film coating treatment, pellet coating Processing. The plant seed or bulb of the present invention is a plant seed or bulb obtained by attaching an effective amount of the composition of the present invention by these methods, and retains an effective amount of the composition of the present invention.
When the composition of the present invention is applied to plant seeds or bulbs, the amount of the pyrimidinone compound applied is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of plant seeds or bulbs. The dose is usually 0.000001 to 50 g, preferably 0.0001 to 30 g per kg of plant seeds or bulbs.

Examples of pests for which the composition of the present invention is effective include harmful insects, harmful mites, harmful nematodes, and phytopathogenic fungi such as filamentous fungi and bacteria. Specific 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), Grape Phylloxera (Daktulosphaira trixiferax) Aphids such as leaf phylloxera (Phylloxera notabilis pergande), Southern pecan leaf phylloxera (Phylloxera russellae Stoetzel); Scotinophara lurida, Malayan ri ce black bug (Scotinophara coarctata), blue beetle (Nezara antennata), bark beetle (Eysarcoris parvus), blue beetle (Halyomorpha mista), southern blue stink bug (Nezara viridula), Egreen Estarc bugs (Nezara viridula), Red banded stink bug (Piezodorus guildinii), Burrower brown bug (Scaptocoris castanea), Oebalus pugnax, Dichelops melacanthus and other stink bugs; Spider helicopter (Leptocorisa acuta), Leptocorisa genus, etc. ) Etc. White lice (Trialeurodes vaporariorum), whitefly (Bemisia tabaci), whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferau) and other whitefly species; Aonidiella 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); (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), Rice leafroller (Marasmia） patnalis), Inatake maki (Marasmia exigua), Cottontail moth (Notarcha derogata), Plodia interpunctella, Awa no Mei teri ), Rice case worms (Nymphula depunctalis), Marasmia, Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shootpiborer aigasaccharalis), Giant Sugarcane borer (Telchin licus), etc .; Spodoptera litura, Spodoptera exera ), Fritiperda (Spodoptera frugiperda), Spodoptera exempta, Agrotis ipsilon, Wakaba (Plusia nigrisigna), Soybean looper (Pseudoplusia includes), Trichoplesias , Helicoverpa spp. (Helicoverpa armigera), etc. Helicobelpa spp., Velvetbean caterpillar (Anticarsia gammatalis), Cotton leafworm (Alabama argillacea), etc .; White butterflies, such as Pieris rapae; Adoxophies genus, Nashihime Nkui (Grapholita molesta), soybean pod borer, Leguminivora glycinivorella (Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses azukivora), apple Coca summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (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 ee Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Cereal Leaf Beetle (Oulema melanopus), Woolly horn beetle (Aulacophora femoralis), Pterol hamde (Phylolta) ), Rice beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), potato flare beetle (Ep) itrix シ cucumeris), rice beetle (Dicladispa armigera), Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivinia impressifrons), etc .; potato fern (Anomala cuprea) Rhizotrogus majalis), carrot beetle (Bothynus gibbosus), Grape Colaspis (Colaspis brunnea), southern Corn leaf beetle (Myochrous denticollis), Holotrichia, June beetle (Phyllophaga crinita), etc. Weevil (Echinocnemus squameus), rice weevil (Lissorhoptrus oryzophilus), weevil (Sphenophorus venatus), etc .; us subsignatus) and Sphenophorus levis and other genus Sphenophorus; epicarunas such as Epilachna vigintioctopunctata; Lyctus brunneus; Japanese beetles; longhorn beetles (Anoplophora malasiaca), longhorn beetles such as Migdolus fryanus; sp., Anchastus sp., Melanotus sp., Limonius sp., Conoderus sp., Ctenicera sp.); Swan beetles, such as Paederus fuscipes, 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.
Lip and limb class: Thereuonema hilgendorfi, Scolopendra subspinipes, etc.
Double-legged class: Japanese red millipede (Oxidus gracilis), Japanese red millipede (Nedyopus tambanus).
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 (Fusarium graminearum, F.avenaceum, F.culmorum, Microdochium nivale), rust (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 disease (Fusar ium graminearum, F.avenaceum, F.culmorum, Microdochium nivale), rust disease (Puccinia striiformis, P.graminis, P.hordei), naked smut (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), Stocro Tomato 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 moniliosis Monilinia mali), rot disease (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose disease (Glomerella cingulata), brown spot disease (Diplocarpon mali) ), Ringworm (Botryosphaeria berengeriana), plague (Phytophtora cactorum); pear black spot (Venturia nashicola, V.pirina), black spot (Alternaria alternata Japanese pear pathotype), red star (Gymnosporangium haraeanum); peach ash Star disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.); Grape black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust Diseases (Phakopsora ampelopsidis), blacklot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycosphaerell) a nawae); Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine split (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 mildew (Elsinoe glycines), black spot (Diaporthe phaseolorum var.sojae) ), Rust (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), stalk disease (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); ), Rust disease (Uromyces appendiculatus), horn spot disease (Phaeoisariopsis griseola), anthracnose disease (Colletotrichum lindemthianum); peanut black astringency (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 (Spongospor) a subterranean f.sp.subterranea), half body wilt disease (Verticillium albo-atrum, V.dahliae, V.nigrescens); strawberry powdery mildew (Sphaerotheca humuli); Cha net rot (Exobasidium reticulatum); 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) , Sclerotial rot (Botrytis squamosa); various crops of gray mold disease (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum); radish black spot disease (Alternaria brassicicola); buckwheat dollar spot disease (Sclerotinia homeocarpa); 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.

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, insecticidal, acaricidal, nematicidal, bactericidal agents other than the target insecticidal, acaricidal, nematicidal, bactericidal agents 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), Tungue disease (Rice tungro spherical virus, Rice tungro bacilliform virus), rice grassy stunt disease (Rice grassy stunt virus), rice rugged stunt disease (Rice ragged stunt virus), rice stripe leaf blight Disease (Rice stripe virus), black stripe atrophy (Rice black streaked dwarf virus), rice southern black stripe atrophy (Southern rice black-streaked dwarf virus), rice hump dwarf disease (Rice gall dwarf virus), rice leaf blight ( Rice hoja blanca virus), white leaf disease (White leaf desease of rice), yellowing dwarf disease (Yellow dwarf virus), Red disease (Rice penyakit merah virus), rice yellow leaf disease (Rice yellow stunt virus), transition yellowing Disease (Rice transitory yellowing virus), rice yellow spot (Rice Yellow Mottle Virus), rice necrotic mosaic virus (Rice necrosis mosaic virus), rice dwarf disease (Rice) dwarf stunt virus), northern wheat mosaic disease (Northern Cereal Mosaic Virus), barley yellow dwarf disease (Barley Yellow Dwarf Virus), wheat yellow leaf disease (Wheat yellow dwarf virus), Oat sterile dwarf (Oat sterile dwarf virus) streak mosaic (Wheat streak mosaic virus), maize mosaic disease (Maize dwarf mosaic virus), Maize stripe disease (maize stripe tenuivirus), Maize chlorotic dwarf (Maize chlorotic dwarf virus), Maize chlorotic mottle (moize chloro), 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 fine spot mosaic disease (Soybean mild mosaic virus) Alfalfa Mosaic Virus, Bean yellow―spot mosaic virus, Soybean mosaic virus, Bean yellow mosaic vir us, Cowpea severe mosaic virus), soybean virus disease (Broad bean wilt virus, Bean common mosaic virus, Peanut stunt virus, Southern bean mosaic virus), soybean dwarf disease (Soybean dwarf luteovirus, Milk-vetch dwarf luteovirus) 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 leaf (Soybean crinkle leaf virus), Soybean severe stunt (Soybean severe stunt virus), Tomato 黄 chlorosis virus, Tomato 黄 spotted wilt virus, Tomato yellow leaf curl virus), Melon yellow spot (MelonMeyellow spot virus), Pumpkin mosaic disease (Watermelon mosaic virus), Dwarf disease (Cucumber mosaic virus) , Zucchini yellow spot mosaic disease (Zucchini yellow mosaic virus), turnip mosaic disease (Turnip mosaic virus), cucurbit yellow spot disease (Cucurbit chlorotic yellows virus), red leaf spot (Capsicum 化 chlorosis virus), cucumber yellow spot ( Beet pseudo yellows virus), chrysanthemum stem disease (chrysanthemum stem necrosis virus), impatiens necrotic spot disease (Impatiens necrotic spot virus), iris yellow spot (Iris マイ yellow spot virus), sweet potato mottle mosaic disease (Sweet potato internal cork) ), Mosaic virus diseases of various plants mediated by sweetpotato potato shrub mosaic disease (Sweet potato shukuyo mosaic virus), Polymixa genus or Olpidium genus.

When the composition of the present invention is used for pest control, the application amount can vary widely depending on the application time, application location, application method, etc., but in general, the pyrimidinone compound and the compound The total amount of is usually 1 to 10,000 g per 10,000 m ² . When the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., the present pyrimidinone compound and the present compound are usually adjusted so that the total concentration thereof is 0.01 to 10,000 ppm. It is diluted with water and applied, and granules, powders and the like are usually applied as they are.

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 that is generally cultivated. Such varieties of plants include plants to which one or more useful traits have been conferred by genetic breeding techniques or genetic recombination techniques (genetically modified plants) and stack varieties in which they are crossed.
Such useful traits include herbicide resistance, pest resistance, disease resistance, stress resistance, and quality improvement of fatty acid residue composition modified crops of fats and oils.

Examples of such a genetically modified plant include, for example, genetic recombination in the electronic information site (http://www.isaaa.org/) of the International Agri-Bio Corporation (INTERRNATIN SERVICE for the ACQUISITION of AGRI-BIOTECH APPLICATIONS, ISAAA). Plants listed in the crop registration database (GM APPROVAL DATABASE). More specifically, plants that have been given environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by genetic recombination techniques, or traits related to growth and yield, product quality, fertility traits, etc. It may be a modified plant.

Plants that have been given herbicide tolerance by genetic recombination technology include protoporphyrinogen oxidase (hereinafter abbreviated as PPO) herbicides such as flumioxazin, 4-hydroxyphenylpyruvate diacids such as isoxaflutol and mesotrione. Oxygenase (hereinafter abbreviated as HPPD) inhibitors, acetolactate synthase (hereinafter abbreviated as ALS) inhibitors such as imazetapyr and thifensulfuron methyl, 5-enolpyruvylshikimate-3-phosphate synthase (such as glyphosate) (Hereinafter abbreviated as EPSP) inhibitors, glutamine synthase inhibitors such as glufosinate, auxin-type herbicides such as 2,4-D and dicamba, and plants to which resistance to herbicides such as bromoxynil has been conferred by genetic recombination technology included.
Examples of plants to which herbicide tolerance has been imparted by gene recombination technology include glyphosate-resistant EPSPS gene (CP4 epsps) derived from Agrobacterium tumefaciens strain CP4, glyphosate metabolizing enzyme derived from Bacillus licheniformis (Glyphosate N-acetyltransferase) gene whose activity is enhanced by shuffling technology, glyphosate metabolic enzyme genes (gat4601, gt6421), glyphosate metabolic enzyme (glyphosate oxidase gene, goxv247) derived from Ochrobacterum strain LBAA Or maize-derived glyphosate tolerance mutation EPSPS gene (mepsps, 2mepsps) having has one or more of the introduced glyphosate tolerant transgenic plants and the like. Maize (Zea mays L.), Soybean (Glycine max L.), Cotton (Gossypium hirsutum L.), Sugar beet (Beta vulgaris), Canola (Brassica napus, Brassica rapaed), Alfalfa .), Wheat (Triticum aestivum), creeping bentgrass (Agrossis tolonifera) and other plants, there are glyphosate-resistant genetically modified varieties.
Several glyphosate-tolerant transgenic plants are commercially available. For example, genetically modified plants that express glyphosate-resistant EPSPS derived from Agrobacterium are trade names including Roundup Ready (registered trademark) and express glyphosate-metabolizing enzyme derived from Bacillus with enhanced metabolic activity by shuffling technology Genetically modified plants are trade names such as Optimum (registered trademark) GAT (registered trademark), Optimum (registered trademark) Gly canola, and transgenic plants expressing EPSPS having a glyphosate-resistant mutation derived from corn are GlyTol (registered trademark). ) Is already sold under the product name.
Similarly, as an example of a plant to which herbicide tolerance has been imparted by genetic recombination technology, phosphinothricin N-acetyltransferase, a glufosinate metabolizing enzyme derived from Streptomyces hygroscopicus, Phosphinothricin N-acetyltransferase, A gene (bar), a phosphinothricin N-acetyltransferase gene (pat), which is a glufosinate metabolizing enzyme derived from Streptomyces virochromogenes, or a glufosinate-tolerant transgenic plant introduced with a synthesized pat gene or the like There is. There are glufosinate-resistant transgenic varieties such as corn, soybean, cotton, canola, rice (Oryza sativa L.), sugar beet, chicory (Cichorium intybus) and the like.
Several glufosinate-tolerant transgenic plants are commercially available. Genetically modified plants that express glufosinate metabolizing enzymes (bar, pat) derived from Streptomyces are already sold under trade names including LibertyLink (registered trademark).
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, bromoxynyl-tolerant gene recombination in which a nitrilase gene (bxn), which is a bromoxynyl-metabolizing enzyme derived from Klebsiella pneumoniae subsp. Ozaenae, has been introduced. There are plants. Bromoxinyl-resistant genetically modified varieties are produced in plants such as canola, cotton, tobacco (Nicotiana tabacum L.), and are already sold under trade names including Navigator (registered trademark) canola or BXN (registered trademark) .
Similarly, as an example of a plant to which herbicide tolerance has been imparted by gene recombination technology, a genetically modified carnation (Dianthus caryophyllus) into which an ALS herbicide-tolerant ALS gene (surB, S4-HrA) derived from tobacco has been introduced as a selection marker ) In addition, a transgenic flax (Linum usitistisumum L.) into which an ALS herbicide-resistant ALS gene derived from Arabidopsis thaliana has been introduced has been developed under the trade name CDC Trifid Flax. In addition, a genetically modified soybean introduced with an ALS herbicide-resistant ALS gene (csr1-2) derived from Arabidopsis thaliana has been developed under the name of Culture (registered trademark). Furthermore, transgenic corn resistant to sulfonylurea and imidazolinone herbicides introduced with corn-derived ALS herbicide-resistant ALS gene (zm-hra), soybean-derived ALS herbicide-resistant ALS gene (gm- There are genetically modified soybeans that are resistant to sulfonylurea herbicides introduced with fra).
Similarly, as an example of a plant to which herbicide resistance has been imparted by genetic recombination technology, an isoxaflutol resistant gene set into which an HPPD herbicide-resistant HPPD gene (hppdPFW336) derived from Pseudomonas fluorescens strain A32 has been introduced. There are modified soybeans and mesotrione-resistant genetically modified soybeans introduced with HPPD gene (avhppd-03) derived from oat (Avena sativa).
Similarly, as an example of a plant to which herbicide tolerance has been imparted by genetic recombination technology, allyloxyalkanoate dioxygenase, which is a 2,4-D metabolizing enzyme derived from Sphingobium herbicidovorans, is exemplified. ) 2,4-D resistance into which the gene (aad-1) or the allyloxyalkanoate dioxygenase gene (aad-12), which is a 2,4-D metabolizing enzyme derived from Delftia acidovorans, has been introduced GM, GM soybean, GM cotton, etc., some of which have been developed under the trade names of Enlist (registered trademark) Maize and Enlist (registered trademark) Soybean. Further, there are dicamba-resistant genetically modified soybeans, transgenic cotton, etc., into which a dicamba monooxygenase gene (dmo) introduced as a dicamba metabolic enzyme derived from Stenotrophomonas maltophilia strain DI-6 is introduced. is there.
Similarly, examples of plants that have been rendered tolerant to two or more herbicides by genetic engineering techniques include transgenic cotton that is resistant to both glyphosate and glufosinate, and genetically modified maize that is GlyTol® LibertyLink. (Registered trademark), Round Ready (registered trademark) LibertyLink (registered trademark) Maize is already sold under the trade name. In addition, a genetically modified soybean resistant to both glufosinate and 2,4-D was developed under the trade name of Enlist (registered trademark) Soybean, and genetically modified cotton resistant to both glufosinate and 2,4-D. There is also. A genetically modified soybean that is resistant to both glyphosate and dicamba has been developed under the trade name Genuity (R) Roundup Ready (R) 2 Xtend (R). Genetically modified maize, soybean, which is resistant to both glyphosate and ALS inhibitors, has been developed under the trade name Optimum® GAT®. In addition, transgenic cotton resistant to both glufosinate and dicamba, transgenic corn resistant to both glyphosate and 2,4-D, transgenic soybean resistant to both glyphosate and HPPD herbicide Has also been developed. In addition, genetically modified soybeans that are resistant to three herbicides, glyphosate, glufosinate and 2,4-D, have also been developed.

Plants to which pest resistance has been imparted by gene recombination technology include plants to which resistance to lepidopterous insects, Coleoptera insects, multiple order insects, nematodes and the like are imparted.
As an example of a plant that has been given resistance to lepidopteran insects by genetic recombination technology, it encodes delta-endotoxin, which is an insecticidal protein derived from soil bacteria Bacillus thuringiensis (hereinafter abbreviated as Bt) And transgenic plants such as corn, soybean, cotton, rice, Populus (Populus sp.), Tomato (Lycopersicon esculentum) and eggplant (Solanum melongena). Cry1A, Cry1Ab, modified Cry1Ab (partially deleted Cry1Ab), Cry1Ac, Cry1Ab-Ac (a hybrid protein in which Cry1Ab and Cry1Ac are fused), Cry1C, Cry1F , Cry1Fa2 (modified cry1F), moCry1F (modified Cry1F), Cry1A. 105 (a hybrid protein in which Cry1Ab, Cry1Ac, and Cry1F are fused), Cry2Ab2, Cry2Ae, Cry9C, Vip3A, Vip3Aa20, and the like.
Examples of plants that have been given resistance to Coleoptera by genetic recombination technology, such as maize, potato, etc., that have been introduced with a gene encoding delta-endotoxin, an insecticidal protein derived from soil bacteria Bt There are plants. Examples of delta-endotoxins that confer resistance to Coleoptera insects include Cry3A, mCry3A (modified Cry3A), Cry3Bb1, Cry34Ab1, and Cry35Ab1.
As an example of a plant imparted with resistance to multiple insects by gene recombination technology, a gene set introduced with a synthetic gene encoding a hybrid protein eCry3.1Ab fused with Cry3A and Cry1Ab derived from soil bacteria Bt Transgenic corn, genetically modified cotton introduced with a gene encoding trypsin inhibitor CpTI derived from cowpea (Vigna unguicula), a gene set introduced with a gene encoding API that is protease inhibitor protein A derived from Kwai (Sagitaria sagittifolia) There is a replacement poplar.
Insecticidal proteins that impart pest resistance to plants include hybrid proteins of the above-mentioned insecticidal proteins, partially missing proteins, and modified proteins. The hybrid protein is produced by a combination of different domains of a plurality of insecticidal proteins using genetic recombination technology, and Cry1Ab-Ac or Cry1A. 105 etc. are known. As a protein lacking a part, Cry1Ab and the like lacking a part of the amino acid sequence are known. Examples of the modified protein include proteins in which one or more amino acids of the natural delta-endotoxin are substituted, and Cry1Fa2, moCry1F, mCry3A and the like are known.
In addition, as insecticidal proteins that impart pest resistance to plants by genetic recombination technology, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae, insecticidal protein Vip1 derived from Bt bacteria , Vip2, Vip3, nematode-derived insecticidal protein, scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin-produced toxin, filamentous fungal toxin, plant lectin, agglutinin, trypsin inhibitor, serine Protease inhibitor, protease inhibitor such as patatin, cystatin, papain inhibitor, lysine, corn-RIP, ribosome inactivating protein (RIP) such as abrin, ruffin, saporin, bryodin, 3-hydroxysterloy Oxidase, ecdysteroid-UDP-glucosyltransferase, steroid metabolic enzymes such as cholesterol oxidase, ecdysone inhibitor, ion channel inhibitors such as HMG-CoA reductase, sodium channel, calcium channel inhibitor, juvenile hormone esterase, diuretic hormone receptor Body, stilbene synthase, bibenzyl synthase, chitinase, glucanase and the like.

In addition, transgenic plants imparted with pest resistance by introducing one or two or more insecticidal protein genes are already known, and some genetically modified plants are commercially available.
Examples of transgenic cotton imparted with pest resistance include Bollgard (registered trademark) cotton that expresses the insecticidal protein Cry1Ac derived from Bt bacteria, and Bollgard II (registered trademark) that expresses the insecticidal proteins Cry1Ac and Cry2Ab derived from Bt bacteria. ) Cotton, Bollgard III (registered trademark) expressing insecticidal proteins Cry1Ac, Cry2Ab, Vip3A derived from Bt bacteria, VIPCOT (registered trademark) expressing insecticidal proteins Vip3A and Cry1Ac derived from Bt bacteria, insecticidal properties derived from Bt bacteria Commercially available recombinant cotton with a trade name including WideStrike (registered trademark) that expresses the proteins Cry1Ac and Cry1F is commercially available.
Examples of genetically modified maize imparted with pest resistance include Yieldgard® Rootworm RW that expresses the insecticidal protein Cry3Bb1 derived from Bt, YieldGard Plus that expresses the insecticidal proteins Cry1Ab and Cry3Bb1 derived from Bt Trademark), insecticidal protein Cry1A. YieldGard (registered trademark) VT Pro (registered trademark) and the like that express 105 and Cry2Ab2 are commercially available. Agrisure (registered trademark) RW expressing insecticidal protein mCry3A derived from Bt bacteria, Agrisure (registered trademark) Viptera expressing insecticidal protein Vip3Aa20 derived from Bt bacteria, Agrisure expressing insecticidal protein eCry3.1 Ab derived from Bt bacteria (Registered trademark) Duracade (registered trademark) and the like are also commercially available.
As examples of genetically modified potatoes imparted with pest resistance, Atlantic NewLeaf (registered trademark) potato, NewLeaf (registered trademark) Russet Burbank poto, etc. that express the insecticidal protein Cry3A derived from Bt bacteria are commercially available.

Plants to which disease resistance has been imparted by gene recombination techniques include common bean (Phaseolus vulgaris), papaya (Carica papaya), plum (Prunus domestica), potato, and Cucurbita pepo. , Sweet pepper (Capsicum annuum), tomato and the like. As a genetically modified plant imparted with resistance to plant viral diseases, specifically, a gene set in which a gene that generates double-stranded RNA of a replica protein of Bean golden mosaic virus is introduced. Recombinant kidney beans, transgenic papaya into which a coat protein gene of Papaya ringspot virus has been introduced, a coat protein gene of Potato virus Y, or a potato leaf roll virus ( Potato leaf roll virus) Recombinant potato introduced with a replication enzyme domain gene, Cucumber mosaic virus coat protein Squeezed gene, watermelon melon mosaic virus coat protein gene, zucchini yellow mosaic virus coat protein gene introduced, recombinant squirt, cucumber mosaic virus There are a genetically modified sweet pepper and a genetically modified tomato introduced with a coat protein gene of (Cucumber mosaic virus).
As an example of a genetically modified potato imparted with resistance to a plant viral disease, a genetically modified potato with a trade name including Newleaf (registered trademark) is commercially available.
Plants imparted with disease resistance also include plants imparted with the ability to produce anti-pathogenic substances having a selective action using genetic engineering techniques. As examples of anti-pathogenic substances, PR proteins and the like are known (PRPs, EP392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP392225, WO199533818, EP353191, and the like. Examples of anti-pathogenic substances include, for example, ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.), stilbene synthase, Microorganisms such as benzyl synthase, chitinase, glucanase, peptide antibiotics, heterocyclic antibiotics, and protein factors involved in plant disease resistance (referred to as plant disease resistance genes and described in WO2003010906) are produced. And anti-pathogenic substances.

For plants whose quality of the product has been modified by genetic recombination technology, modification of lignin production, modification of oil or fatty acid component, production of phytate degrading enzyme, modification of flower color, modification of alpha amylase activity, modification of amino acid Genetically modified plants with modified product quality such as starch or carbohydrate component modification, suppression of acrylamide production, reduction of black spots due to mechanical damage, antiallergic properties, reduction of nicotine production, aging or ripening delay, etc. It is done.
Alfalfa-derived S-adenosyl-L-methionine involved in lignin production: Trans-caffeoyl CoA A gene that generates double-stranded RNA of 3-methyltransferase (ccomt) gene was introduced to reduce lignin content by RNA interference. There is a genetically modified alfalfa.
A transgenic canola whose triacylglyceride content, including lauric acid, has been increased by introducing a 12: 0 ACP thioesterase gene derived from Laurel (Umbellaria californica) involved in fatty acid synthesis under the trade name Laurical (registered trademark) Canola. Has been developed.
A genetically modified canola that enhances the degradation of endogenous phytic acid by introducing a 3-phytase gene (phyA) derived from Aspergillus niger, a plant phytic acid degrading enzyme, is a product of Phytaseed (registered trademark) Canola. Developed under the trade name. Similarly, genetically modified maize has been developed in which degradation of endogenous phytic acid is enhanced by introducing a black mold-derived 3-phytase gene (phyA).
Dihydroflavonol-4-reductase gene from Petunia hybrida, an enzyme that produces the blue pigment delphinidin and its derivatives, and petunia, pansy (Viola wittrockiana), salvia (Salvia splendens), or flavonoid from carnation A genetically modified carnation in which the flower color is controlled to be blue by introducing a -3 ′, 5′-hydroxylase gene is known. The genetically modified carnations in which the flower color is controlled to blue are Moondust (registered trademark), Moonshadow (registered trademark), Moonshade (registered trademark), Moonlite (registered trademark), Moonaqua (registered trademark), Moonvista (registered trademark), Moonique ( It has been developed under trade names such as (registered trademark), Moonpearl (registered trademark), Moonberry (registered trademark), and Moonvelvet (registered trademark). Furthermore, by introducing an anthocyanin-5-acyltransferase gene derived from Torenia sp., An enzyme that produces the blue pigment delphinidin and its derivatives, and a flavonoid-3 ′, 5′-hydroxylase gene derived from pansy A genetically modified rose whose flower color is controlled to blue has also been developed.
There is a genetically modified maize that has enhanced bioethanol production by introducing a thermostable alpha-amylase gene (amy797E) of Thermococcales sp. For starch degradation under the trade name of Enogen (R) Has been developed.
Genetically modified maize enhanced lysine production by introducing a dihydrodipicolinate synthase gene (cordapA) from Corynebacterium glutamicum for the production of lysine, an amino acid, includes Mavera® Developed under the trade name.
Genetically modified melons and genetically modified tomatoes have been developed that have improved shelf life by introducing the S-adenosylmethion hydrolase gene (sam-K) derived from E. coli bacteriophage T3 related to ethylene production of plant hormones . In addition, a gene lacking a part of the ACC synthase gene derived from tomato involved in ethylene production of plant hormones, an ACC deaminase gene derived from Pseudomonas chlororaphis that degrades ethylene precursor ACC, and pectin on the cell wall Tomato-derived polygalacturonase gene double-stranded RNA or a tomato-derived ACC oxidase gene involved in ethylene production has been introduced to improve genetic shelf tomatoes. ing. A genetically modified tomato improved in shelf life by introducing a gene that generates double-stranded RNA of a polygalacturonase gene derived from tomato has been developed under the trade name FLAVR SAVR (registered trademark).
Genes that generate double-stranded RNA of transcription factor genes that promote starch degradation from potato, genes that generate double-stranded RNA of polyphenol oxidase gene derived from potato, and genes that are involved in asparagine production Products that include Innate (registered trademark), a genetically modified potato that reduces the possibility of starch degradation, black spot formation due to mechanical damage, and generation of carcinogenic substances (acrylamide) by heating Developed by name. In addition, a genetically modified potato having a reduced amylose content by introducing an antisense gene of starch synthase derived from potato has been developed under the trade name of Amflora (registered trademark).
Genetically modified rice has been developed that has an immunotolerant effect and a hay fever alleviating effect by introducing a modified cedar pollen antigen protein gene (7crp).
By introducing a partial gene (gm-fad2-1) of soybean-derived ω-6 desaturase derived from soybean, which is a fatty acid desaturase, genetically modified soybean that suppresses the gene expression and enhances the oleic acid content is known as Plenish ( (Registered trademark) or Treus (registered trademark). In addition, a gene that produces double-stranded RNA of soybean-derived acyl-acyl carrier protein thioesterase gene (fatb1-A) and a double-stranded RNA of soybean-derived δ-12 desaturase gene (fad2-1A) Genetically modified soybeans having a reduced saturated fatty acid content by introducing a gene to be produced have been developed under the trade name of Visual Gold (registered trademark). In addition, a genetically modified soybean in which the content of ω3 fatty acid is enhanced by introducing a δ-6 desaturase gene (Pj.D6D) derived from primrose and a δ-12 desaturase gene (Nc.Fad3) derived from red bread fungus has been developed. Yes.
A genetically modified tobacco having a reduced nicotine content by introducing an antisense gene of tobacco-derived quinolinate phosphoribosyltransferase gene (NtQPT1) has been developed.
A phytoene synthase gene (psy) derived from Narcissus pseudonarcissus and a carotene desaturase gene (crt1) derived from a soil bacterium that synthesizes carotenoids (Erwinia uredovora) is introduced into β-endosperm tissue and expressed in the endosperm tissue. -Golden rice, a genetically modified rice that can produce carotene and harvest rice containing vitamin A, has also been developed.

Plants whose fertility traits and the like have been modified by gene recombination techniques include genetically modified plants in which the plants are given male sterility and fertility recovery traits. There are genetically modified maize and genetically modified chicory imparted with male sterility by expressing a ribonuclease gene (barnase) derived from Bacillus amyloliquefaciens in cocoon tapetum cells. In addition, there is a genetically modified maize imparted with male sterility by introducing a DNA adenine methylase gene (dam) derived from E. coli. Furthermore, a gene set in which fertility traits are controlled by introducing an alpha-amylase gene (zm-aa1) derived from corn that gives male sterility traits and an ms45 protein gene (ms45) derived from maize that gives fertility recovery traits There is also a replacement corn.
There is a genetically modified canola imparted with a function of restoring fertility by expressing a ribonuclease-inhibiting protein gene (barstar) derived from Bacillus bacteria in cocoon tapetum cells. Further, a gene set in which fertility traits are controlled by expressing a ribonuclease gene (barnase) derived from Bacillus that gives male sterile traits and a ribonuclease inhibitor protein gene (barstar) derived from Bacillus that gives fertility recovery traits There is also a replacement canola.

Examples of plants that have been imparted with environmental stress tolerance by genetic recombination technology include genetically modified plants with drought tolerance. A drought-tolerant corn introduced with a cold shock protein gene (cspB) derived from Bacillus subtilis has been developed under the trade name of Genuity (registered trademark) DraughtGard (registered trademark). Furthermore, a drought-resistant sugarcane into which a choline dehydrogenase gene (RmBetA) derived from alfalfa rhizobia (Rhizobium meliloti) or Escherichia coli has been developed.

Examples of plants whose growth and yield traits have been modified by genetic engineering techniques include genetically modified plants with enhanced growth ability. For example, genetically modified soybeans and the like into which a gene (bbx32) encoding a transcription factor that controls diurnal properties derived from Arabidopsis thaliana has been developed.

The plant in the present invention may be a plant modified using a technique other than the genetic recombination technique. More specifically, it may be a plant imparted with environmental stress resistance, disease resistance, herbicide resistance, pest resistance, etc. by classical breeding technology, genetic marker breeding technology, genome editing technology, or the like.
Examples of plants to which herbicide tolerance has been imparted by classical or genetic marker breeding techniques include corn, rice, wheat, sunflower (Helianthus annuus), canola, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, Lentils (Lens culinaris) and the like are sold under the trade name of Clearfield (registered trademark). Moreover, STS soybean etc. which are sulfonylurea type | system | group herbicide tolerance soybean are examples of the plant to which tolerance to sulfonyl type | system | group ALS inhibition type herbicides, such as thifensulfuron methyl, was provided by the classic or gene marker breeding technique. Similarly, SR corn, which is cetoxydim-resistant maize, is an example of a plant to which tolerance is imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical or genetic marker breeding techniques. is there.
An example of a plant to which pest resistance is imparted by classical or genetic marker breeding techniques is soybean having a Rag1 (Resistance Aphid Gene 1) gene that is an aphid resistance gene. Moreover, as a plant imparted with nematode tolerance by a classical breeding method, soybean imparted with resistance to cyst nematode, cotton imparted with resistance to root knot nematode, and the like can be mentioned.
As a plant to which disease resistance has been imparted by classical or genetic marker breeding techniques, resistance to corn and gray leaf spot that have been imparted resistance to anthracnose disease is given. Resistant corn, resistant to Goss's wilt, resistant to Fusarium stalk rot, resistant to Asian soybean rust Soybeans, Peptotolerant to Phytophathora, Lettuce tolerant to powdery mildew, Tomato tolerant to Bacterial wilt And tomatoes with resistance to geminivirus, lettuce with resistance against downy mildew, and the like.
As an example of a plant to which drought tolerance has been imparted by classical or gene marker breeding techniques, drought-tolerant maize has been developed under the trade names of Agurisure Artesian (registered trademark) and Optimum AQUAmax (registered trademark). Also,
As an example of a plant to which herbicide resistance has been imparted by genome editing technology, a sulfonylurea herbicide is introduced by a rapid variety development technology that introduces a sulfonylurea herbicide resistance mutation into an ALS gene via a DNA and RNA chimeric oligonucleotide. A canola imparted with resistance has been developed under the trade name SU Canola®.

In addition, for the above-mentioned plants, using genetic recombination technology, classical breeding technology, genetic marker breeding, or genome editing technology, environmental stress resistance, disease resistance, herbicide resistance, pest resistance, Two or more types of properties possessed by the parental line by crossing two or more lines with growth, yield traits, product quality, fertile traits, etc., and genetically modified plants with similar or different properties The assigned line is also included. An example of such a plant is a genetically modified plant imparted with both herbicide resistance and pest resistance.
For example, as a transgenic plant imparted with glyphosate resistance and pest resistance, Round Ready (registered trademark) Bollgard (registered trademark) cotton, Round Ready (registered trademark) Bollgard II (registered trademark) cotton, Round Ready (registered trademark) Trade names of Flex (registered trademark) Bollgard II (registered trademark) cotton, Bollgard (registered trademark) III x Roundup Ready (registered trademark) Flex (registered trademark), VIPCOT (registered trademark) Roundup Ready Flex (registered trademark) Cotton, etc. Genetically modified cotton has been developed. In addition, Agurisure (registered trademark) GT / RW, Round Ready (registered trademark) YieldGuard (registered trademark) maize, Genuity (registered trademark) VT Double Pro (registered trademark), Genuity (registered trademark) VT Triple Pro (registered trademark), YieldGard (R), YieldGard (R) CB + RW, YieldGard (R) VT (R) Rootworm (R) RR2, YieldGard (R) RW + RR, YieldGard (R) VTTriGr (R) A genetically modified corn having a trade name such as Plus with RR has been developed. In addition, genetically modified soybeans such as Intatta (registered trademark) Roundup Ready (registered trademark) 2 Pro have been developed.
For example, as a genetically modified plant imparted with glufosinate resistance and pest resistance, products such as Widestrike (registered trademark) Cotton, Twinlink (registered trademark) Cotton, Fibermax (registered trademark) LibertyLink (registered trademark) Bollgard II (registered trademark) Named genetically modified cotton has been developed. Also, Agriure (registered trademark) CB / LL, Agriure (registered trademark) CB / LL / RW, Agriure (registered trademark) Viptera (registered trademark) 2100, Agriure (registered trademark) Viptera (registered trademark) 3100, Bt Xtra (registered trademark). (Trademark) Maize, NatureGard Knockout (registered trademark), Herculex (registered trademark) RW, Herculex (registered trademark) CB, Herculex (registered trademark) XTRA, Starlink (registered trademark) Maize, Liberty Link (registered trademark) YieldGard registered trademark A genetically modified corn having a trade name such as Maize has been developed.
For example, as a genetically modified plant imparted with glyphosate resistance, glufosinate resistance, and pest resistance, Widestrike (registered trademark) Roundup Ready (registered trademark) Cotton, Widestrike (registered trademark) Roundup Ready Flex (registered trademark) Cotton, Registered trademark x Round Ready Flex (registered trademark) x VIPCOT (registered trademark) Cotton, Glytol (registered trademark) x Twinlink (registered trademark) and the like have been developed. In addition, Agurisure (registered trademark) GT / CB / LL, Agurisure (registered trademark) 3000GT, Agrisure (registered trademark) 3122, Agrisure (registered trademark) Viptera (registered trademark) 3110, Agrisure (registered trademark) Viptera 3111, Registered Trademark) Viptera 3220, Agurisure (registered trademark) Duracade (registered trademark) 5122, Agrisure (registered trademark) Duracade (registered trademark) 5222, Optimum (registered trademark) Intrict, Optimum (registered trademark) TRIsect, Optimum (registered trademark) InTRtrust , Optimum (TM) Intrasect Xtreme, Genuity (R) Sma Genetic recombination of trade names such as rtStax (registered trademark), Power Core (registered trademark), Herculex (registered trademark) I RR, Herculex (registered trademark) RW Roundup Ready (registered trademark) 2, Herculex XTRA (registered trademark) RR Corn is being developed.
For example, a genetically modified cotton having a trade name such as BXN (registered trademark) Plus Bollgard (registered trademark) Cotton has been developed as a genetically modified plant imparted with bromoxynyl resistance and pest resistance.

As an example of a line provided with two or more of the above-mentioned plural traits, there is a genetically modified plant provided with disease resistance and pest resistance. For example, as a genetically modified plant imparted with resistance to potato virus Y (Potato virus Y) and pest resistance, Hi-Lite NewLeaf (registered trademark) Y Potato, NewLeaf (registered trademark) Y Russet Burbank Potato, SheepodyNe (Trademark) Y Potato, or a genetically modified plant imparted with resistance to potato leaf roll virus and pest resistance, and a gene group with a trade name such as NewLeaf (registered trademark) Plus Russset Burbank Potato Replacement potatoes have been developed.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant provided with herbicide resistance and modified product quality. For example, genetically modified canola and genetically modified maize imparted with glufosinate resistance and fertile traits have been developed under the trade names of InVigor (registered trademark) Canola and InVigor (registered trademark) Maize.
An example of a line provided with two or more of the above-mentioned plural traits is a genetically modified plant imparted with pest resistance and modified product quality. For example, genetically modified maize imparted with traits that enhance resistance to lepidopterous pests and lysine production has been developed under the trade name of Mavera (registered trademark) Yieldgard (registered trademark) Maize.
In addition, as an example of a strain provided with two or more of the above-mentioned plural traits, a genetically modified plant provided with herbicide tolerance and a modified fertility trait, a gene provided with herbicide tolerance and environmental stress tolerance Recombinant plants, genetically modified plants with herbicide resistance and modified growth and yield traits, genetically modified plants with herbicide resistance, pest resistance, and modified product quality, herbicides Genetically modified plants imparted with resistance, pest resistance, and environmental stress resistance have been developed.

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 pyrimidinone compound.

Production Example 1 (1)
1.28 g of 4-chloro-6-methoxypyrimidine, 1.48 g of [2-fluoro-4- (trifluoromethyl) phenyl] boronic acid pinacol ester, 0.28 g of tetrakis (triphenylphosphine) palladium (0), sodium carbonate A mixture of 6.3 mL of aqueous solution (2M) and 15 mL of DME was stirred at 80 degrees for 3 hours. After completion of the reaction, water was added to the reaction mixture allowed to cool to room temperature, extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to obtain 0.99 g of intermediate (1-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.89 (1H, s), 8.28 (1H, dd), 7.56 (1H, d), 7.46 (1H, d), 7.29 (1H, s), 4.05 (3H, s ).

Production Example 1 (2)
To a reaction mixture of 0.97 g of the intermediate (1-1) and 15 mL of NMP, 0.29 mL of ethanethiol and 0.17 g of sodium hydride (oil, 60%) were sequentially added under ice cooling, and the mixture was stirred at room temperature for 1 day. Water was added to the reaction mixture, the precipitated solid was collected by filtration, and the filtrate was concentrated under reduced pressure to obtain 1.03 g of intermediate (1-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, s), 7.61-7.55 (2H, m), 7.49 (1H, d), 7.01 (1H, s), 4.06 (3H, s), 2.95 (2H , q), 1.30 (3H, t).

Production Example 1 (3)
To a mixture of 0.98 g of intermediate (1-2) and 15 mL of chloroform, 1.58 g of mCPBA (70%) was added under ice cooling, and the mixture was stirred at room temperature for 1.5 hours. A 10% aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, the organic layer was dried over anhydrous sodium sulfate, and the organic layer was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.91 g of intermediate (1-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, s), 8.42 (1H, s), 7.97 (1H, d), 7.59 (1H, d), 6.89 (1H, s), 4.06 (3H, s ), 3.68 (2H, q), 1.34 (3H, t).

Production Example 1 (4)
A mixture of 0.86 g of intermediate (1-3) and 10 mL of concentrated hydrochloric acid was stirred with heating under reflux for 2 hours. The reaction mixture allowed to cool to room temperature was poured into water, and sodium hydroxide was added. The precipitated solid was collected by filtration and concentrated under reduced pressure to obtain 0.74 g of intermediate (1-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, s), 8.17 (1H, s), 7.99 (1H, d), 7.64 (1H, d), 6.64 (1H, s), 3.67 (2H, q ), 1.37 (3H, t).

Production Example 1 (5)
To a mixture of 0.23 g of the intermediate (1-4), 0.27 g of cesium carbonate and 3 mL of NMP, 0.29 g of 2,2,2-trifluoroethyl nonafluorobutanesulfonate was added at room temperature, and the mixture was stirred at room temperature for 3 hours. did. After adding water to the reaction mixture and extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 0.14 g of the present pyrimidinone compound 1 represented by the following formula and 0.13 g of by-product 1.
This pyrimidinone compound 1

By-product 1

¹ H-NMR (CDCl ₃ ) δ: 8.82 (1H, s), 8.43 (1H, s), 8.00 (1H, d), 7.61 (1H, d), 7.03 (1H, s), 4.88 (2H, q ), 3.68 (2H, q), 1.35 (3H, t).

Production Example 2
Instead of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate, 2,2,3,3,3-pentafluoropropyl = trifluoromethanesulfonate was used, and the method described in Production Example 1 (5) was used. Accordingly, the present pyrimidinone compound 2 and by-product 2 represented by the following formula were obtained.
This pyrimidinone compound 2

Byproduct 2

¹ H-NMR (CDCl ₃ ) δ: 8.82 (1H, s), 8.43 (1H, s), 7.99 (1H, d), 7.61 (1H, d), 7.03 (1H, s), 4.95 (2H, t ), 3.69 (2H, q), 1.36 (3H, t).

Production Example 3
Described in Production Example 1 (5) using 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate instead of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate According to the method, the pyrimidinone compound 3 and the by-product 3 represented by the following formula were obtained.
This pyrimidinone compound 3

By-product 3

¹ H-NMR (CDCl ₃ ) δ: 8.83 (1H, s), 8.43 (1H, s), 8.00 (1H, d), 7.60 (1H, d), 7.01 (1H, s), 5.20-5.02 (1H , m), 4.90-4.82 (2H, m), 3.68 (2H, q), 1.35 (3H, t).

Production Example 4 (1)
Using 4-chloro-6-methoxy-5-methylpyrimidine instead of 4-chloro-6-methoxypyrimidine and following the method described in Production Example 1 (1), an intermediate represented by the following formula (4 -1) was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.72 (1H, s), 7.63-7.57 (1H, m), 7.55 (1H, d), 7.44 (1H, d), 4.07 (3H, s), 2.08 (3H , d).

Production Example 4 (2)
By using intermediate (4-1) instead of intermediate (1-1), intermediate (4-2) represented by the following formula was obtained according to the method described in Production Example 1 (2). .

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, s), 7.59 (1H, s), 7.49 (1H, d), 7.29 (1H, d), 4.07 (3H, s), 2.91 (2H, q ), 1.98 (3H, s), 1.27 (3H, t).

Production Example 4 (3)
The intermediate (4-3) represented by the following formula was obtained by using the intermediate (4-2) instead of the intermediate (1-2) according to the method described in Production Example 1 (3). .

¹ H-NMR (CDCl ₃ ) δ: 8.63 (1H, s), 8.41 (1H, s), 7.97 (1H, d), 7.47 (1H, d), 4.07 (3H, s), 3.51-3.27 (2H , m), 1.96 (3H, s), 1.27 (3H, t).

Production Example 4 (4)
A mixture of 0.98 g of intermediate (4-3) and 5 mL of concentrated hydrochloric acid was stirred with heating under reflux for 1 hour. The reaction mixture was allowed to cool to room temperature, added to water, extracted with methyl-tert-butyl ether (hereinafter referred to as MTBE), and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 0.83 g of intermediate (4-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.41 (1H, s), 8.10 (1H, s), 7.99 (1H, d), 7.52 (1H, d), 3.53-3.32 (2H, m), 1.94 (3H , s), 1.31 (3H, t).

Production Example 4 (5)
Intermediate (4-3) is used instead of intermediate (1-3), and 2,2,3,3,3-pentafluoro is used instead of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate The present pyrimidinone compound 4 and by-product 4 represented by the following formula were obtained using propyl = trifluoromethanesulfonate according to the method described in Production Example 1 (5).
This pyrimidinone compound 4

By-product 4

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, s), 8.42 (1H, s), 7.99 (1H, d), 7.48 (1H, d), 5.17-4.96 (1H, m), 4.89-4.69 (1H, m), 3.52-3.25 (2H, m), 2.01 (3H, s), 1.28 (3H, t).

Production Example 5
Intermediate (4-3) was used in place of intermediate (1-3), and 2,2,3,4,4,4- in place of 2,2,2-trifluoroethyl = nonafluorobutanesulfonate Using hexafluorobutyl = trifluoromethanesulfonate, the pyrimidinone compound 5 represented by the following formula and a by-product 5 were obtained according to the method described in Production Example 1 (5).
This pyrimidinone compound 5

By-product 5

¹ H-NMR (CDCl ₃ ) δ: 8.65 (1H, s), 8.42 (1H, s), 8.00 (1H, d), 7.48 (1H, d), 5.18-4.69 (3H, m), 3.51-3.26 (2H, m), 2.01 (3H, s), 1.28 (3H, t).

Production Example 6 (1)
To a mixture of 6 g of 4,6-dichloropyrimidine and 40 mL of methanol, 8.16 g of 28% sodium methoxide methanol solution was added dropwise under ice cooling. After stirring for 2 hours under ice cooling, the mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the resulting oily substance, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the organic layer was dried over sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting oily substance was subjected to silica gel chromatography to obtain 4.6 g of an intermediate (6-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, s), 6.78 (1H, dd), 4.01-3.95 (3H, m).

Production Example 6 (2)
While cooling a mixture of 6.9 g of 1,4-diazabicyclo [2,2,2] octane and MTBE to −40 ° C., 39 mL of 1.0 M butyl lithium hexane solution was added dropwise. The reaction mixture was stirred at −40 ° C. for 2 hours and then cooled to −50 ° C., and 5.0 g of 3-fluoropyridine was added dropwise to the reaction mixture. After further stirring at −50 ° C. for 2 hours, 17 mL of tributylstannyl chloride was added dropwise to the reaction mixture. The reaction mixture was stirred at −50 ° C. for 6 hours, then warmed to room temperature, and saturated aqueous ammonium chloride solution was added. The reaction mixture was extracted with MTBE. The organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 23 g of a mixture containing intermediate (6-2) represented by the following formula.

^{_{1 H-NMR (CDCl 3)}} δ: 8.62-8.56 (1H, m), 7.25-7.11 (2H, m), 1.69-0.76 (45H, m).

Production Example 6 (3)
To a mixture of 6.0 g of the intermediate (6-2) mixture, 1.0 g of the intermediate (6-1) and 28 mL of toluene, 810 mg of tetrakis (triphenylphosphine) palladium, 130 mg of copper iodide and anhydrous lithium chloride at room temperature 430 mg was added. The reaction mixture was stirred for 6 hours under reflux. The reaction mixture was allowed to cool to room temperature, and 500 mg of intermediate (6-1) was added. The reaction mixture was further stirred for 9 hours under heating to reflux. The reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 960 mg of intermediate (6-3) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.97 (1H, d), 8.63-8.60 (1H, m), 7.61-7.55 (1H, m), 7.47-7.42 (2H, m), 4.06 (3H, s) .

Production Example 6 (4)
To a mixture of 1.4 g of the intermediate (6-3) and 22 mL of DMF, 290 mg of sodium hydride (60% oil) and 510 μL of ethanethiol were sequentially added under ice cooling. After stirring at room temperature for 3 hours, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 1.7 g of intermediate (6-4) represented by the following formula.

^{_{1 H-NMR (CDCl 3)}} δ: 8.92 (1H, d), 8.46 (1H, dd), 7.72 (1H, dd), 7.36 (1H, d), 7.33-7.29 (1H, m), 4.05 (3H , s), 2.93 (2H, q), 1.33 (3H, t).

Production Example 6 (5)
Using intermediate (6-4) instead of intermediate (1-2), intermediate (6-5) represented by the following formula was obtained according to the method described in Production Example 1 (3). .

¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, dd), 8.80 (1H, d), 8.48 (1H, dd), 7.61 (1H, dd), 7.18 (1H, d), 4.05 (3H, s ), 3.92 (2H, q), 1.38 (3H, t).

Production Example 6 (6)
A mixture of 1.8 g of intermediate (6-5) and 10 mL of concentrated hydrochloric acid was stirred with heating at 90 ° C. for 6 hours, and then the mixture was concentrated under reduced pressure. Ethanol was added to the obtained residue, and the precipitated solid was filtered and washed with ethanol to obtain 1.6 g of an intermediate (6-6) represented by the following formula.

¹ H-NMR (DMSO-D ₆ ) δ: 8.94 (1H, dd), 8.41 (1H, dd), 8.32 (1H, d), 7.81 (1H, dd), 6.59 (1H, d), 3.79 (2H , q), 1.20 (3H, t).

Production Example 6 (7)
To a mixture of 150 mg of the intermediate (6-6) and 4 mL of chloroform, 260 μL of diisopropylethylamine and 140 μL of 2,2,2-trifluoroethyl = trifluoromethanesulfonate were sequentially added at room temperature. The reaction mixture was heated and stirred at 75 ° C. for 2 hours. The resulting reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 130 mg of the pyrimidinone compound 6 represented by the following formula.

Production Example 7
Using 2,2,3,3,3-pentafluoropropyl = trifluoromethanesulfonate instead of 2,2,2-trifluoroethyl = trifluoromethanesulfonate, the method described in Preparation Example 6 (7) Accordingly, the present pyrimidinone compound 7 represented by the following formula was obtained.

Production Example 8
According to the method described in Production Example 6 (7), using 2,2,3,3-tetrafluoropropyl = trifluoromethanesulfonate instead of 2,2,2-trifluoroethyl = trifluoromethanesulfonate. The present pyrimidinone compound 8 and by-product 8 represented by the following formula were obtained.
This pyrimidinone compound 8

By-product 8

¹ H-NMR (CDCl ₃ ) δ: 8.90 (1H, dd), 8.83 (1H, d), 8.49 (1H, dd), 7.64 (1H, dd), 7.32 (1H, d), 6.16-5.85 (1H , m), 4.91-4.82 (2H, m), 3.92 (2H, q), 1.39 (3H, t).

Production Example 9
As described in Preparation Example 6 (7), 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate was used instead of 2,2,2-trifluoroethyl = trifluoromethanesulfonate. According to the method, the pyrimidinone compound 9 and the by-product 9 represented by the following formula were obtained.
This pyrimidinone compound 9

By-product 9

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, dd), 8.83 (1H, d), 8.50 (1H, dd), 7.64 (1H, dd), 7.32 (1H, d), 5.21-5.00 (1H , m), 4.90-4.81 (2H, m), 3.92 (2H, q), 1.40 (3H, t).

Production Example 10
Using 2,2,3,3,4,4,5,5-octafluoropentyl = trifluoromethanesulfonate instead of 2,2,2-trifluoroethyl = trifluoromethanesulfonate, Preparation Example 6 (7 The pyrimidinone compound 10 represented by the following formula was obtained according to the method described in (1).

Production Example 11
According to the method described in Preparation Example 6 (7), using 4,4,4-trifluorobutyl iodide instead of 2,2,2-trifluoroethyl = trifluoromethanesulfonate, This pyrimidinone compound 11 was obtained.

Production Example 12 (1)
To a mixture of 54 g of 3-chloropyridine-2-carbonitrile and 300 mL of THF, 500 g of 1M methylmagnesium bromide THF solution was added dropwise under ice cooling. The reaction mixture was stirred for 2 hours under ice cooling. The obtained reaction mixture was added to 2N hydrochloric acid under ice cooling, and the mixture was stirred for 30 minutes. A 1N aqueous sodium hydroxide solution was added to the mixture to adjust the pH to 8, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 58 g of intermediate (12-1) represented by the following formula.

^{_{1 H-NMR (CDCl 3)}} δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

Production Example 12 (2)
Intermediate (12-2) represented by the following formula was obtained according to the method described in Production Example 6 (4), using Intermediate (12-1) instead of Intermediate (6-3).

¹ H-NMR (CDCl ₃ ) δ: 8.40 (1H, dd), 7.69 (1H, dd), 7.37 (1H, dd), 2.92 (2H, q), 2.72 (3H, s), 1.40 (3H, t ).

Production Example 12 (3)
To a mixture of 3.6 g of intermediate (12-2) and 20 mL of dimethyl carbonate, sodium hydride (oil, 60%) was added under ice-cooling and stirred for 30 minutes. The reaction mixture was heated to 50 ° C. and stirred for 4 hours. After cooling to room temperature, the reaction mixture was added to 0.5N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the obtained solid was washed with an MTBE / hexane mixed solvent (1:10) to obtain 4.6 g of an intermediate (12-3) represented by the following formula.

^{_{1 H-NMR (CDCl 3)}} δ: 8.38 (1H, dd), 7.69 (1H, d), 7.38 (1H, dd), 4.19 (2H, s), 3.72 (3H, s), 2.93 (2H, q ), 1.41 (3H, t).

Production Example 12 (4)
To a mixture of 4.6 g of intermediate (12-3) and 38 mL of formamide, 7.3 g of ammonium acetate was added at room temperature. The reaction mixture was heated and stirred at 100 ° C. for 4 hours, and then allowed to cool to room temperature. Water was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the obtained solid was washed with an MTBE / hexane mixed solvent (1:10) to obtain 3.7 g of an intermediate (12-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.39 (1H, d), 7.65 (1H, d), 7.26 (1H, dd), 5.21 (1H, s), 3.73 (3H, s), 2.94 (2H, q ), 1.34 (3H, t).

Production Example 12 (5)
To a mixture of 5.0 g of intermediate (12-4) and 21 mL of NMP, 20 g of 28% sodium methoxide methanol solution was added under ice cooling. The reaction mixture was heated and stirred at 100 ° C. for 2 hours, and then allowed to cool to room temperature. To this reaction mixture was added a 1N aqueous sodium hydroxide solution under ice cooling, and the mixture was washed with chloroform. The obtained aqueous layer was adjusted to pH 4 with 6N hydrochloric acid and extracted with chloroform. This organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the obtained solid was washed with MTBE to obtain 4.2 g of an intermediate (12-5) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.48 (1H, dd), 8.30 (1H, s), 7.72 (1H, d), 7.32 (1H, dd), 7.05 (1H, s), 2.94 (2H, q ), 1.35-1.32 (3H, m).

Production Example 12 (6)
To a mixture of 12 g of Intermediate (12-5) and 170 mL of chloroform, 25 g of mCPBA (70%) was added under ice cooling. The reaction mixture was stirred for 3 hours under ice cooling, and then 350 mL of chloroform was added. The reaction mixture was extracted with 4N hydrochloric acid. The aqueous layer was washed with a dimethyl sulfide-chloroform mixed solution (1: 100), and the aqueous layer was dried under reduced pressure. Ethanol was added to the resulting residue, and the precipitated solid was filtered and washed with ethanol to obtain 12 g of an intermediate (12-6) represented by the following formula.

Production Example 12 (7)
To a mixture of 400 mg of the intermediate (12-6) and 3 mL of chloroform, 930 μL of diisopropylethylamine, 32 mg of 4- (dimethylamino) pyridine and 580 mg of 1,1,3-trichloro-1-propene were sequentially added at room temperature. The reaction mixture was heated and stirred at 50 ° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the obtained residue was subjected to silica gel chromatography to obtain 370 mg of the pyrimidinone compound 12 represented by the following formula.

Production Example 13 (1)
To a mixture of 10 g of 3,6-dichloropyridine-2-carboxylic acid and 52 mL of toluene, 9.8 mL of thionyl chloride was added at room temperature. The reaction mixture was heated and stirred at 110 ° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to give an oily substance.

Production Example 13 (2)
To a mixture of 6.9 g of anhydrous magnesium chloride and 104 mL of THF, 11 g of methyl potassium malonate was added at room temperature. The reaction mixture was stirred at room temperature for 2 hours. To this reaction mixture, the whole amount of the oily substance obtained in Production Example 13 (1) and 14 mL of triethylamine were sequentially added under ice cooling. The reaction mixture was warmed to room temperature and stirred at room temperature for 12 hours. 300 mL of 2N hydrochloric acid was added to the obtained reaction mixture under ice cooling, and the mixture was stirred at room temperature for 3 hours. The resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 7.9 g of intermediate (13-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 7.79 (1H, d), 7.43 (1H, d), 4.13 (2H, s), 3.74 (3H, s).

Production Example 13 (3)
Using intermediate (13-2) instead of intermediate (12-3), intermediate (13-3) represented by the following formula was obtained according to the method described in Preparation Example 12 (4). .

¹ H-NMR (CDCl ₃ ) δ: 7.75 (1H, d), 7.31 (1H, d), 5.41 (1H, s), 3.73 (3H, s).

Production Example 13 (4)
To a mixture of 2.4 g of intermediate (13-3) and 23 mL of NMP, 840 mg of sodium hydride (60%, oily) and 1.6 mL of ethanethiol were sequentially added under ice cooling. The reaction mixture was warmed to room temperature and stirred for 6 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was dried under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2.7 g of intermediate (13-4) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 7.50 (1H, d), 7.12 (1H, dd), 5.27 (1H, s), 3.73 (3H, s), 3.16 (2H, q), 2.89 (2H, q ), 1.38 (3H, t), 1.28 (3H, t).

Production Example 13 (5)
To a mixture of 2.7 g of intermediate (13-4), 1.8 mL of formamide and 18 mL of NMP, 1.4 g of sodium hydride (60%, oily) was added under ice cooling. The reaction mixture was heated and stirred at 100 ° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and adjusted to pH 4 with 2N hydrochloric acid. The precipitated solid was filtered and washed with hydrochloric acid adjusted to pH 4 to obtain 2.7 g of a crude product of intermediate (13-5) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.30 (1H, s), 7.54 (1H, d), 7.18 (1H, d), 7.16 (1H, s), 3.21 (2H, q), 2.89 (2H, q ), 1.39 (3H, t), 1.31 (3H, t).

Production Example 13 (6)
To a mixture of 2.7 g of the crude intermediate (13-5) product and 19 mL of chloroform, 4.4 g of 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate and diisopropylethylamine were added under ice cooling. 3.3 mL was added sequentially. The reaction mixture was stirred at 50 ° C. for 10 hours. The reaction mixture was allowed to cool to room temperature, 2N hydrochloric acid was added, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2.6 g of the present pyrimidinone compound 13 represented by the following formula.

Production Example 14
To a mixture of 2.6 g of the present pyrimidinone compound 13 and 28 mL of chloroform, 5.3 g of mCPBA (70%) was added under ice cooling. The reaction mixture was warmed to room temperature and stirred for 6 hours. To this reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and sodium sulfite, and the mixture was stirred at room temperature for 30 minutes. The resulting reaction mixture was extracted with chloroform. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 2.28 g of the present pyrimidinone compound 14 represented by the following formula.

Production Example 15
To a mixture of 300 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 260 μL of a 40% dimethylamine aqueous solution was added at room temperature. The reaction mixture was stirred at room temperature for 4.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 240 mg of the pyrimidinone compound 15 represented by the following formula.

Production Example 16
To a mixture of 300 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 70 μL of pyrrolidine was added at room temperature. The reaction mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 260 mg of the pyrimidinone compound 16 represented by the following formula.

Production Example 17
To a mixture of 300 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 122 mg of 28% sodium methoxide methanol solution was added under ice cooling. The reaction mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 210 mg of the pyrimidinone compound 17 represented by the following formula.

Production Example 18
To a mixture of 300 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 44 mg of 1H-1,2,4-triazole and 30 mg of sodium hydride (60%, oily) were successively added under ice cooling. The reaction mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 210 mg of the pyrimidinone compound 18 represented by the following formula.

Production Example 19 (1)
A mixture of 5 g of the intermediate (12-2) and 30 ml of N, N-dimethylformamide dimethyl acetal was stirred for 3 days while heating under reflux. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, and the precipitated solid was collected by filtration. The solid was washed with hexane and dried under reduced pressure to obtain 6.28 g of intermediate (19-1) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.35 (1H, dd), 7.82 (1H, br s), 7.65 (1H, dd), 7.28-7.24 (1H, m), 6.16 (1H, br s), 3.14 (3H, br s), 2.95 (3H, br s), 2.89 (2H, q), 1.37 (3H, t).

Production Example 19 (2)
A mixture of 2.36 g of intermediate (19-1), 0.72 g of urea, 4.1 g of sodium ethoxide (20% ethanol solution) and 10 mL of ethanol was stirred with heating under reflux for 2 hours. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water and concentrated hydrochloric acid were added, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain 2.52 g of compound A.

Production Example 19 (3)
To a mixture of 0.46 g of compound A, 0.77 g of diisopropylethylamine and 5 mL of chloroform, 0.96 g of 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate was added at room temperature, and heated under reflux for 3 hours. Stir. After adding water to the reaction mixture and extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the obtained residue was subjected to silica gel column chromatography to obtain 0.22 g of the present pyrimidinone compound 19 represented by the following formula.

Production Example 19 (4)
To a mixture of 0.29 g of this pyrimidinone compound 19 and 10 ml of chloroform, 0.37 g of mCPBA (75%) was added under ice cooling, and the mixture was stirred at room temperature for 3 hours. A 10% aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.08 g of the present pyrimidinone compound 20 represented by the following formula and 0.15 g of the present pyrimidinone compound 21.
This pyrimidinone compound 20

This pyrimidinone compound 21

Production Example 20 (1)
Description of Production Example 19 (3) using 2,2,3,3-tetrafluoropropyl = trifluoromethanesulfonate instead of 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate The pyrimidinone compound 22 represented by the following formula was obtained according to the above method.

Production Example 20 (2)
Using this pyrimidinone compound 22 instead of this pyrimidinone compound 19, this pyrimidinone compound 23 and this pyrimidinone compound 24 represented by the following formulas were obtained according to the method described in Production Example 19 (4).
The pyrimidinone compound 23

This pyrimidinone compound 24

Production Example 21 (1)
Using 2,2,3,3,4,4,5,5-octafluoropentyl = trifluoromethanesulfonate instead of 2,2,3,3-tetrafluoropropyl = trifluoromethanesulfonate, Preparation Example 19 (3 The pyrimidinone compound 25 represented by the following formula was obtained according to the method described in).

Production Example 21 (2)
Using this pyrimidinone compound 25 instead of this pyrimidinone compound 19, this pyrimidinone compound 26 and this pyrimidinone compound 27 represented by the following formulas were obtained according to the method described in Production Example 19 (4).
This pyrimidinone compound 26

This pyrimidinone compound 27

Production Example 22
To a mixture of 200 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 40 μL of 2,2,2-trifluoroethanol and 18 mg of sodium hydride (60%, oily) were sequentially added. The reaction mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 160 mg of the pyrimidinone compound 28 represented by the following formula.

Production Example 23
To a mixture of 200 mg of the present pyrimidinone compound 14 and 1 mL of DMF, 0.20 mL of diisopropylethylamine and 180 mg of 5-aminomethyl-2-chlorothiazole hydrobromide were sequentially added. The reaction mixture was stirred with heating at 100 ° C. for 20 hours. After allowing to cool to room temperature, 0.20 mL of diisopropylethylamine and 180 mg of 5-aminomethyl-2-chlorothiazole hydrobromide were further added to the reaction mixture. The reaction mixture was stirred with heating at 100 ° C. for 10 hours. After allowing to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 76 mg of the pyrimidinone compound 29 represented by the following formula.

Production Example 24
Using 1,1,2-trifluoro-4-bromo-1-butene instead of 1,1,3-trichloro-1-propene, according to the method described in Preparation Example 12 (7), This pyrimidinone compound 30 represented by the formula was obtained.

Production Example 25
Using 1,1,1,2,2,2-pentafluoro-4-iodobutane instead of 1,1,3-trichloro-1-propene, according to the method described in Preparation Example 12 (7), This pyrimidinone compound 31 represented by the formula was obtained.

Production Example 26
The method described in Production Example 12 (7) using 1,1,1,2,2,3,3-heptafluoro-5-iodopentane instead of 1,1,3-trichloro-1-propene In this manner, the present pyrimidinone compound 32 represented by the following formula was obtained.

Production Example 27
To a mixture of 1.0 g of the present pyrimidinone compound 9 and 6 mL of toluene was added 940 mg of 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetan-2,4-disulfide. . The reaction mixture was stirred at 110 ° C. with heating under reflux for 6 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.1 g of the present pyrimidinone compound 33 represented by the following formula.

Production Example 28
This pyrimidinone compound 34 represented by the following formula was obtained according to the method described in Production Example 15 using 28% aqueous ammonia instead of 40% aqueous dimethylamine.

Production Example 29 (1)
To a mixture of 30 g of 3-chloro-5- (trifluoromethyl) pyridine-2-carboxylic acid and 130 mL of toluene, 25 mL of thionyl chloride and 1.6 mL of DMF were sequentially added at room temperature. The reaction mixture was stirred at 110 ° C. for 5 hours. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to give an oily substance.

Production Example 29 (2)
To a mixture of 22 g of anhydrous magnesium chloride and 270 mL of THF, 32 g of methyl potassium malonate was added at room temperature. The reaction mixture was stirred at 50 ° C. for 1 hour. To this reaction mixture, the whole amount of the oily substance obtained in Production Example 28 (1) and 65 mL of triethylamine were sequentially added under ice cooling. The reaction mixture was warmed to room temperature and stirred at room temperature for 12 hours. 400 mL of 2N hydrochloric acid was added to the obtained reaction mixture under ice cooling, and the mixture was stirred at room temperature for 2 hours. The resulting reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 29 g of intermediate (28-2) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.79 (1H, d), 8.08 (1H, d), 4.17 (2H, s), 3.73 (3H, s).

Production Example 29 (3)
Using intermediate (28-2) instead of intermediate (12-3), intermediate (28-3) represented by the following formula was obtained according to the method described in Production Example 12 (4). .

¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.06 (1H, d), 5.41 (1H, s), 3.74 (3H, s).

Production Example 29 (4)
Intermediate (28-4) represented by the following formula was obtained according to the method described in Production Example 6 (4) using Intermediate (28-3) instead of Intermediate (6-3).

¹ H-NMR (CDCl ₃ ) δ: 8.60 (1H, d), 7.78 (1H, d), 5.23 (1H, s), 3.74 (3H, s), 2.99 (2H, q), 1.38 (3H, t ).

Production Example 29 (5)
To a mixture of 5.0 g of intermediate (28-4) and 16 mL of NMP, 9.0 g of potassium tert-butoxide was added under ice cooling. The reaction mixture was stirred at 80 ° C. for 2 hours and then allowed to cool to room temperature. To this reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution with ice cooling, and the mixture was washed with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, so as to obtain 4.4 g of a crude product of intermediate (28-5) represented by the following formula.

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.30 (1H, d), 7.85 (1H, d), 7.06 (1H, d), 2.99 (2H, q), 1.37 (3H, t ).

Production Example 29 (6)
To a mixture of 4.4 g of the crude product of intermediate (28-5) and 28 mL of chloroform, 2.9 mL of diisopropylethylamine and 2,2,3,4,4,4-hexafluorobutyl = trifluoromethanesulfonate 3 were added at room temperature. .5 g was added sequentially. The reaction mixture was stirred at 50 ° C. for 6 hours. The resulting reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography to obtain 1.4 g of the present pyrimidinone compound 35 represented by the following formula.

Production Example 29 (7)
Using this pyrimidinone compound 35 instead of this pyrimidinone compound 19, this pyrimidinone compound 36 represented by the following formula was obtained according to the method described in Production Example 19 (4).

Formula (1-6)

[Wherein R ¹ represents an ethyl group, R ²¹ represents a hydrogen atom, and G, R ²² , R ²³ , R ³ , R ^3a , and n are defined in the following [Table 14] to [Table 15]. Represents any combination of the descriptions. ] Can be produced by the method described above.
[Table 14]

[Table 15]

The physical property values of the pyrimidinone compound are described below.
[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

[Table 21]

Next, specific compositions of the composition of the present invention will be described below.
In addition, the composition which has the combination as described in [Table A] is attached | subjected and numbered as described in [Table A]. For example, the composition of No. 1 in [Table A] is referred to as the present composition 1.
In [Table A], * described in the column of component 1 represents any one of the pyrimidinone compounds 1 to 57, and the numbers described in [] in the column of each component are the numbers in the present invention. The amount (part) of each component relative to 100 parts of the composition is meant. “Β2” represents the bactericidal compound β2.

[Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

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Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

Continuation of [Table A]

The present compositions 841-1680
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of tebuconazole instead of 2 parts of metconazole.

The present composition 1681-2520
A composition using 2 parts of difenoconazole instead of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].

This composition 2521-3360
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of triticonazole instead of 2 parts of metconazole.

This composition 3361-4200
A composition using 2 parts of prothioconazole instead of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].

This composition 4201-5040
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole instead of 2 parts of metconazole.

This composition 5041-5880
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of diniconazole M instead of 2 parts of metconazole.

This composition 5881-6720
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of ipconazole instead of 2 parts of metconazole.

The present compositions 6721-7560
A composition using 2 parts of prochloraz in place of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].

This composition 7561-8400
A composition using 2 parts of fluquinconazole instead of 2 parts of metconazole in each of the present compositions 1 to 840 described in [Table A].

This composition 8401-9240
In each of Compositions 1 to 840 described in [Table A], a composition using 2 parts of triazimenol instead of 2 parts of metconazole.

The present compositions A1 to A9240
A composition further comprising 10 parts clothianidin and 10 parts chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions B1 to B9240
A composition further containing 10 parts clothianidin and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions C1 to C9240
A composition comprising 10 parts of clothianidin and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions D1 to D9240
A composition comprising 10 parts of imidacloprid and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions E1 to E9240
A composition further containing 10 parts imidacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions F1 to F9240
A composition further comprising 10 parts of imidacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions G1 to G9240
A composition further comprising 10 parts thiamethoxam and 10 parts chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

A composition further comprising 10 parts thiamethoxam and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions I1 to I9240
A composition further comprising 10 parts thiamethoxam and 10 parts fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions J1 to J9240
A composition further comprising 10 parts thiacloprid and 10 parts chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions K1 to K9240
A composition further comprising 10 parts thiacloprid and 10 parts cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions L1 to L9240
A composition further comprising 10 parts of thiacloprid and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions M1 to M9240
A composition further comprising 10 parts of furpyraziflon and 10 parts of chlorantraniliprol in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition N1 to N9240
A composition further comprising 10 parts of flupiradiflon and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

This composition O1-O9240
A composition further comprising 10 parts of furpyradiflon and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions P1 to P9240
A composition further comprising 20 parts of clothianidin in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions Q1 to Q9240
A composition further comprising 10 parts of the insecticidal compound α and 10 parts of chlorantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions R1 to R9240
A composition comprising 10 parts of the insecticidal compound α and 10 parts of cyantraniliprole in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

The present compositions S1 to S9240
A composition comprising 10 parts of insecticidal compound α and 10 parts of fipronil in each combination of the present compositions 1 to 9240 (provided that the composition is 100 parts)

Next, formulation examples are shown.

Formulation Example 1
5 parts of one of the pyrimidinone compounds 1 to 57, 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 pulverizing and mixing 10 parts of the pyrimidinone compounds 1 to 57, 10 parts of clothianidin, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 75 parts of synthetic hydrous silicon oxide, Get the agent.

Formulation Example 3
1 part of the present pyrimidinone compounds 1 to 57, 0.5 part of clothianidin, 1 part of synthetic silicon hydrous 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
After mixing 10 parts of the present pyrimidinone compounds 1 to 57, 2 parts of clothianidin, 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. 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 present compounds and amounts used described in [Table i] were used to obtain respective formulations.
[Table i]

[Continuation of Table i]

Formulation Examples 74-142
In Formulation Example 2, in place of 10 parts of clothianidin, the same operations as in Formulation Example 2 are carried out except that the present compounds and amounts used in [Table ii] are used to obtain respective formulations.

[Table ii]

[Continuation of Table ii]

Formulation Examples 143 to 211
In Formulation Example 3, in place of 0.5 part of clothianidin, the same operations as in Formulation Example 3 were carried out except that the present compounds and amounts used described in [Table iii] were used to obtain respective formulations.

[Table iii]

[Continuation of Table iii]

Formulation Examples 212 to 241
In Formulation Example 4, in place of 2 parts of clothianidin, the same operation as in Formulation Example 4 is carried out except that the present compound and the amount used described in [Table iv] are used to obtain each formulation.

[Table iv]

Formulation Example 242
After mixing 10 parts of this pyrimidinone compound 1-57, 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 procedure as in Formulation Example 242 was performed except that 0.1 part of tebuconazole was used and the present compound and the amount used described in [Table v] were used to obtain each formulation.

[Table v]

Formulation Example 281
The present compositions 1-9240, A1˜, obtained by adding 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts. A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

Formulation Example 282
The present compositions 1 to 9240, A1 to A9240, B1 to B9240, C1 to C3, obtained by adding 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and synthetic silicon hydroxide so that the total amount becomes 100 parts C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, N1 to N9240, O1 to O9240, Each wettable powder is obtained by thoroughly pulverizing and mixing any one of P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240.

Formulation Example 283
Compositions 1 to 9240, A1 to A15 obtained by adding 15 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water so that the total amount becomes 100 parts. A9240, B1 to B9240, C1 to C9240, D1 to D9240, E1 to E9240, F1 to F9240, G1 to G9240, H1 to H9240, I1 to I9240, J1 to J9240, K1 to K9240, L1 to L9240, M1 to M9240, Each flowable preparation is obtained by pulverizing any one of N1 to N9240, O1 to O9240, P1 to P9240, Q1 to Q9240, R1 to R9240, and S1 to S9240 by a wet pulverization method.

Next, application examples of the composition of the present invention to plant seeds will be shown.

Application example 1
200 kg of any one of the flowable preparations obtained by the method described in Preparation Example 281 or 283 is smeared on 100 kg of dried sorghum seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 180 grams of oxabetalinyl is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, and each treated seed is obtained by a smearing treatment as described above.

Application example 2
200 kg of any one of the flowable preparations obtained by the method described in Preparation Example 281 or 283 is smeared on 100 kg of dried sorghum seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.
In addition, 40 grams of flxophenim is added to 200 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283, and each treated seed is obtained by smearing in the same manner as described above.

Application example 3
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried corn seed using a rotary seed processing machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the corn, a genetically modified corn containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application example 4
40 kg of dry seed of corn, 40 ml of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283, using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH) Thus, each treated seed is obtained.

Application example 5
100 kg of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried corn seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application Example 6
Each treated seed is obtained by subjecting 10 kg of dried corn seed to 50 g of any one of the wettable powders obtained by the method described in Formulation Example 282.

Application example 7
20 kg of dried soybean seeds are smeared with 20 ml of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283 using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the soybean, a genetically modified soybean containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application example 8
100 kg of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283 is smeared on 10 kg of dried soybean seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained.

Application example 9
50 kg dry seeds, 50 ml of any one of the flowable preparations obtained by the method described in Formulation Example 281 or 283, are smeared using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Thus, each treated seed is obtained. As the cotton, a genetically modified cotton containing a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 10
Apply 50 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried oilseed rape using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment. As the oilseed rape, a genetically modified oilseed rape including a glyphosate resistance gene or a Bt crystal toxin protein gene is used.

Application Example 11
Apply 10 ml of any flowable formulation obtained by the method described in Formulation Example 281 or 283 to 10 kg of dried oilseed rape seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Each treated seed is obtained by treatment.

Application Example 12
Apply 50 ml of any one of the flowable formulations obtained by the method described in Formulation Example 281 or 283 to 10 kg of dry wheat seeds using a rotary seed processor (seed dresser, Hans-Ulrich Hege GmbH). To obtain each treated seed

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

Test example 1
The pyrimidinone compound is dissolved in the mixed solution using 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) per 1 mg of the pyrimidinone compound. Water containing 0.02% by volume of a spreading agent is added thereto, and a chemical solution containing the pyrimidinone compound is prepared so that the concentration of the pyrimidinone compound becomes a predetermined concentration.
Using 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio) per 1 mg of the present compound, the present compound is dissolved in the mixed solution. 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 a chemical solution containing the present compound so that the concentration of the present compound is a predetermined concentration. To prepare.
A chemical solution containing the present pyrimidinone 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 housed 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 pyrimidinone compound and the present compound are the concentrations shown in Table 22 below exhibit excellent control efficacy.

[Table 22]

[Continuation of Table 22]

[Continuation of Table 22]

[Continuation of Table 22]

[Continuation of Table 22]

[Continuation of Table 22]

[Continuation of Table 22]

Test example 2
By seeding any one of the treated seeds of corn obtained by the method described in Application Example 3 at a depth of 5 cm using a seeder at an interval of 15 cm, Rhizotonia solani and Pythium spp. ), High control effect can be obtained against Negusare nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

Test example 3
By sowing any one of soybean treated seeds obtained by the method described in Application Example 7, high control against Fusarium oxysporum, Rhizoctonia solani, and soybean cyst nematode An effect can be obtained. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

Test example 4
By sowing any one of the oilseed rape treated seeds obtained by the method described in Application Example 10, it is possible to obtain a high control effect against Rhizotonia solani and Negusale nematode. When seeds treated with a preparation containing an insecticide are used, it is possible to obtain a high control effect against pests having the control effect of the insecticide.

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

Claims

Formula (1):

[Where:
A 1 represents a nitrogen atom or CR 4 ;
A 2 and A 3 are those in which A 2 represents a nitrogen atom and A 3 represents CR 3b , or A 2 represents CR 3a and A 3 represents a nitrogen atom,
Q represents an oxygen atom or a sulfur atom,
G is a C2-C10 haloalkyl group, a C3-C10 haloalkenyl group, a C3-C10 haloalkynyl group, a (C1-C5 alkyl) -O- (C2-C5 alkyl) group having one or more halogen atoms, one or more (C3-C5 alkenyl) -O— (C2-C5 alkyl) group having a halogen atom, (C3-C5 alkynyl) -O— (C2-C5 alkyl) group having one or more halogen atoms, one or more halogen atoms (C1-C5 alkyl) -S (O) m- (C2-C5 alkyl) group having one or more, (C3-C5 alkenyl) -S (O) m- (C2-C5 alkyl) group having one or more halogen atoms A (C3-C5 alkynyl) -S (O) m- (C2-C5 alkyl) group having one or more halogen atoms, or a (C1-C5 alkyl) -C having one or more halogen atoms (O)-(C1-C5 alkyl) group,
R 1 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
R 2 is one or more halogen atoms which may have a C1-C6 chain hydrocarbon group, one or more atoms a phenyl group which may have a group selected from the group A, selected from the group B Any of the five-membered aromatic heterocyclic groups selected from the group C (the five-membered aromatic heterocyclic group may have one or more atoms or groups selected from the group A). 6-membered aromatic heterocyclic group (the 6-membered aromatic heterocyclic group may have one or more atoms or groups selected from group A), any one of groups 3- 7-membered non-aromatic heterocyclic group (The 3-7-membered non-aromatic heterocyclic group may have one or more atoms or groups selected from the group consisting of halogen atoms and C1-C6 alkyl groups. ), OR 7, NR 8 R 9, NR 8 C (O) R 10, NR 8 C (O) OR 11, NR 8 C (O) NR 12 R 13 N = CHNR 12 R 13, N = S (O) x R 12 R 13, S (O) y R 12, C (O) OR 8, cyano group, or a halogen atom,
R 4 represents a hydrogen atom or a halogen atom,
R 3 , R 3a and R 3b each independently represent a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a halogen atom;
R 7 has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms An optionally (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group is one or more atoms selected from group A or May have.) Represent,
R 8 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, or one or more halogen atoms. Represents a C3-C6 alkynyl group optionally having,
R 9 has a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C3-C6 alkenyl group optionally having one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms (C1-C3 alkyl) -O- (C1-C3 alkyl) group which has one or more halogen atoms (C1-C3 alkyl) -S (O) y- (C1-C3 alkyl) group which may have one or more halogen atoms C3-C7 cycloalkyl group which may have one or more halogen atoms (C3-C7 cycloalkyl)-(C1-C3 alkyl) group, C1-C6 alkyl group having one cyano group, phenyl C1-C3 alkyl group (the phenyl of the phenyl C1-C3 alkyl group) The minute may have one or more atoms or groups selected from group A), or (5- or 6-membered heteroaryl) C1-C6 alkyl group (the (5- or 6-membered heteroaryl) C1-C6 The 5- or 6-membered heteroaryl part of the alkyl group may have one or more atoms or groups selected from group A),
R 10 is a hydrogen atom, one or more halogen atoms optionally may C1-C6 alkyl group which may have one or more halogen atoms optionally may C3-C6 alkenyl group which may have, have a one or more halogen atoms A C3-C6 alkynyl group which may have one or more, a C3-C7 cycloalkyl group which may have one or more halogen atoms, and a C3-C7 cycloalkyl group which may have one or more halogen atoms (C3-C7 cycloalkyl)- A (C1-C3 alkyl) group or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R 11 is a C1-C6 alkyl group which may have one or more halogen atoms, a C3-C6 alkenyl group which may have one or more halogen atoms, and one or more halogen atoms. A C3-C6 alkynyl group which may have one or more halogen atoms, a C3-C7 cycloalkyl group which may have one or more halogen atoms, and a (C3-C7 cycloalkyl)-(C1- C3 alkyl) group or a phenyl C1-C3 alkyl group (the phenyl portion of the phenyl C1-C3 alkyl group may have one or more atoms or groups selected from group A);
R 12 and R 13 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R 14 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, or one or more halogen atoms Represents a C2-C6 alkoxycarbonyl group optionally having
n represents 0, 1, or 2;
m represents 0, 1, or 2;
p represents 0, 1, 2 or 3 (in the case where p represents 2 or 3, R 2 may be the same or different from each other);
x represents 0 or 1,
y represents 0, 1, or 2.
Group A: C1-C6 alkyl group optionally having one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms A good C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a cyano group, and A group consisting of halogen atoms.
Group B:

Group C:

Group D:

And a compound represented by
A pest control composition comprising one or more compounds selected from the following group (a) or the following group (b).
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 compounds represented by the following formula

A group of competitive modulators of nicotinic acetylcholine receptors.
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 Sodium channel modulator consisting of praretrin, pyrethrin, resmethrin, silafluophene, tefluthrin, kappafluthrin, tetramethrin, tetramethylfluthrin, tralomethrin, transfluthrin, benfluthrin, flufenprox, flumethrin, flamethrin, methfluthrin, profluthrin and dimefluthrin. .
Subgroup a-3:
A group of GABAergic chloride channel blockers consisting of ethiprol, fipronil and flupiprol, and a group of GABAergic chloride channel allosteric modulators consisting of afoxolanel, fluralanel, brofuranilide and floxamethamide.
Subgroup a-4:
A group of ryanodine receptor modulators consisting of chlorantraniliprole, cyantranylprolol, cyclaniliprol, fulvendiamide, tetraniliprol 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 A group of carbamate acetylcholinesterase inhibitors consisting of thiophanox, triazamate, trimetacarb, XMC and xylylcarb.
Subgroup a-6:
A group of nematicidal active compounds 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 A group of microbial materials consisting of, 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 of sterol biosynthesis inhibitors consisting of nazole.
Subgroup b-2:
Azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, fluphenoxystrobin, floxastrobin, cresoxime-methyl, mandestrobin, methinostrobin, A group of Qo inhibitors consisting of orissastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyroxystrobin, trifloxystrobin, pyribencarb, triclopyricarb, cyazofamid and amisulbrom.
Subgroup b-3:
A group of RNA polymerase I inhibitors 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 of succinate dehydrogenase inhibitors consisting of (methyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide.
Subgroup b-5:
A group of β-tubulin polymerization inhibitors consisting of benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide and ethaboxam.
Subgroup b-6:
Multi-acting contact active compound consisting of felbam, manzeb, manneb, methyleum, propineb, thiuram, dineb, ziram, captan, captahol, holpet, chlorothalonil, tolylfluanid, guazatine, iminotadine, anilazine, dithianone, quinomethionate and fluorimide Group of.
Subgroup b-7:
A group of cellulose synthesis inhibitors consisting of dimethomorph, flumorph, pyrimorph, benchavaricarb, benchavaricarb isopropyl, iprovaricarb, varifenalate and mandipropamide.
Subgroup b-8:
A group of MAP / histidine kinase inhibitors in osmotic signaling consisting of fenpicuronyl, fludioxonil, clozolinate, iprodione, procymidone and vinclozolin.
Subgroup b-9:
A group of other fungicides consisting of tolcrofos methyl, oxathiapiproline, pical butrazox, fluopicolide and silthiofam.
The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) to one or more compounds selected from the group (a) is 100: 1 to 1: 100 by weight. Control composition.
The pest according to claim 1, wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (a) is 10: 1 to 1:10 by weight. Control composition.
The pest according to claim 1, wherein the content ratio of the compound represented by the formula (1) to one or more compounds selected from the group (b) is 10,000: 1 to 1: 100 by weight. Control composition.
The pest according to claim 1, wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (b) is 1000: 1 to 1:10 by weight. Control composition.
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, comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 5 to a plant, plant seeds, bulbs, or soil where plants are grown.
Plant seeds or bulbs to which an effective amount of the pest control composition according to any one of claims 1 to 5 is attached.