WO2015147199A1 - Nematicide composition, and method for controlling nematodes - Google Patents

Abstract

Specifically provided is a novel noxious organism-controlling agent composition for controlling nematodes. The nematicide composition contains, as active ingredients, an oxime-substituted amide compound represented by formula (I), an N-oxide thereof, or a salt of these compounds. [G¹ denotes G¹-1 or G¹-27 for example, G² denotes G²-2 for example, W denotes an oxygen atom for example, X¹ denotes a difluoromethyl group or a trifluoromethyl group for example, X², X³, X⁴ and X⁵ each independently denote a hydrogen atom for example, Y¹ denotes a halogen atom for example, Y² denotes a hydrogen atom or a halogen atom for example, Y³ denotes a halogen atom, a trifluoromethyl group, a C₂-C₆ alkynyl group for example, Y⁴ denotes a hydrogen atom for example, R¹ denotes a C₁-C₆ alkyl group or a C₁-C₄ haloalkyl group for example, R² and R³ each denote a hydrogen atom or a methyl group for example, R⁴ denotes a hydrogen atom for example, and R⁵ denotes a methyl group for example]

Description

Nematicidal composition and method for controlling nematode

The present invention relates to a nematicidal composition containing a specific oxime-substituted amide compound, its N-oxide or a salt thereof as an active ingredient, and a method for using the same. Furthermore, the present invention relates to a nematicidal composition comprising an active ingredient compound of a known nematicide.

The oxime substituted amide compound represented by the formula (I), its N-oxide or a salt thereof, which is an active ingredient compound of the present invention, is a known compound, and its activity as a pest control agent is known ( Patent Document 1).
Moreover, in this invention, the compound described as the active ingredient B which is a 2nd active ingredient is a well-known nematicide, disinfection, or an insecticide (refer nonpatent literature 1).

International Publication No. 2014/010737

Nematode damage caused by infection with various nematodes on plants such as cereals, fruit trees, vegetables, and ornamental plants causes serious damage such as deterioration in the quality of crops, drastic reduction in yield, and in some cases death of plants. , It causes great economic losses not only for producers but also for consumers. Therefore, effective control of these nematodes is a very important issue in order to achieve efficient and stable crop production. From such a point of view, conventionally, development of a control agent for the purpose of controlling nematodes has progressed, and many effective agents have been put to practical use up to now.
However, due to the long-term use of such drugs, in recent years, nematodes have acquired drug resistance, and there are an increasing number of scenes where it is difficult to control with existing plant disease control agents that have been used. Also, some existing nematicides are highly toxic, or some remain perturbed in the environment for long periods of time, causing problems that disrupt the ecosystem. Under such circumstances, development of a novel nematicide and effective nematode control method that has not only excellent control activity against nematodes but also high control properties such as low toxicity and low persistence. Is always expected.
An object of the present invention is to provide a novel nematode control composition and control method that exhibits excellent control activity against nematodes and has properties such as low toxicity and low persistence.

As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have selected an oxime-substituted amide compound represented by the following formula (I), an N-oxide or a salt thereof, or 2 selected from them: A composition comprising an active ingredient comprising a mixture of two or more species and, if necessary, an effective amount of one or more additional components selected from known nematicides, fungicides, insecticides and acaricides It was found that the product exhibits excellent nematode control activity. Moreover, it discovered that it showed the outstanding nematode control activity by processing this composition to the soil used for cultivation of the seed of a target crop plant body, or the said plant, and completed this invention.
That is, the present invention uses the nematicide composition described in the following [1] to [18] (hereinafter referred to as the present composition) and the composition of the present invention described in [19] to [22]. The present invention relates to a method for controlling nematodes (hereinafter referred to as the method of the present invention).

[1] A nematicidal composition comprising an oxime-substituted amide compound represented by the formula (I), an N-oxide thereof or a salt thereof as an active ingredient.

[Wherein G ¹ is G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7, G ¹ -8, G ¹ -9, G ¹ -11, G ¹ -12, G ¹ -13, G ¹ -16, G ¹ -27, G ¹ -32, G ¹ -33 or G ¹ -50,

G ² represents the structure of G ² -1, G ² -2, G ² -6 or G ² -9,

W represents an oxygen atom or a sulfur atom,
X ¹ represents a halogen atom, nitro, methyl, ethyl or C ₁ -C ₂ haloalkyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure represented by G ¹ -27 and X ¹ represents dihalomethyl, X ² represents a hydrogen atom. ,
X ³ represents a hydrogen atom, methyl or ethyl,
X ⁴ represents a hydrogen atom,
X ⁵ represents a hydrogen atom, a fluorine atom or a chlorine atom,
Y ¹ represents a hydrogen atom, a halogen atom, methyl, trifluoromethyl or methoxy,
Y ² represents a hydrogen atom, a halogen atom, cyano, C ₁ -C ₃ alkoxy or methylthio,
Y ³ is optionally substituted by a hydrogen atom, a halogen atom, cyano, C ₁ -C ₄ alkyl, trifluoromethyl, C ₂ -C ₄ alkenyl, C ₂ -C ₆ alkynyl, R ⁶ (C ₂ -C ₆ ) represents alkynyl, —OR ⁷ , C ₁ -C ₄ alkylthio, —C (R ⁸ ) = NOR ⁹ , phenyl, D-3 or D-7,
Y ⁴ represents a hydrogen atom or a halogen atom,
Y ⁵ represents a hydrogen atom,

R ¹ is, C ₁ ~ C ₆ alkyl, C ₁ ~ C ₄ haloalkyl, substituted by _{^{R 10 (C 1 ~ C 4}} ) alkyl, C ₃ ~ C ₆ cycloalkyl, C ₃ ~ C ₆ alkenyl, C ₃ Represents -C ₄ haloalkenyl, C ₃ -C ₆ alkynyl or phenyl;
R ² is a hydrogen atom, methyl or ethyl, provided that represents a structure in which G ¹ is represented by ^{G 1} -1, X ¹ represents a chlorine atom, is X ^2, X ^3, X ⁴ and ^{X 5} In the case where it represents a hydrogen atom, G ² represents a structure represented by G ² -1, Y ³ represents a chlorine atom, and Y ¹ , Y ² , Y ⁴ and Y ⁵ represent a hydrogen atom, R ² represents methyl or ethyl;
R ³ represents a hydrogen atom or methyl, or R ³ together with R ² forms an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ² and R ³ are bonded. Represents
R ⁴ represents a hydrogen atom, cyclopropyl, C ₁ -C ₂ alkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
R ⁵ represents methyl or ethyl,
R ⁶ represents a halogen atom, C ₃ -C ₆ cycloalkyl, hydroxy (C ₃ -C ₆ ) cycloalkyl, C ₅ -C ₆ cycloalkenyl, —OH, —OR ⁷ , C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylsulfonyloxy, C ₁ -C ₄ alkylthio, trimethylsilyl, -C (R ⁸ ) = NOR ⁹ , phenyl, phenyl substituted by (Z) _m or D-32,
Z represents a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, methoxy, trifluoromethoxy, trifluoromethylthio or phenyl, and when m or n represents 2 or more, each Z May be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs form -CH = CH-CH = CH- A 6-membered ring may be formed together with the carbon atom to which Z of
R ⁷ is substituted by C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-14, C ₃ -C ₄ alkynyl or (Z) _m Represented phenyl,
R ⁸ represents a hydrogen atom or methyl,
R ⁹ represents methyl or ethyl,
R ¹⁰ is cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-5, E-9, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, trimethylsilyl, -C ( R ¹¹ ) = NOR ¹² , phenyl, phenyl substituted by (Z) _m , D-10 or D-32;
D-3, D-7, D-10 and D-32 each represent an aromatic heterocycle having the following structural formula;

E-5, E-9 and E-14 each represent a saturated heterocyclic ring of the following structural formula,

R ¹¹ represents methyl,
R ¹² represents methyl or ethyl,
m represents an integer of 1, 2 or 3,
n represents an integer of 0, 1 or 2. ]

[2] G ¹ is G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7, G ¹ -11, G ¹ -12, G ¹ -16, G ¹ -27 or G ^1- Representing 33 structures,
G ² represents the structure of G ² -1, G ² -2 or G ² -9,
W represents an oxygen atom,
X ¹ represents a halogen atom, nitro, methyl, difluoromethyl or trifluoromethyl,
X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure of G ¹ -27 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom,
X ³ represents a hydrogen atom or methyl,
Y ¹ represents a fluorine atom, a chlorine atom or a bromine atom,
Y ² represents a hydrogen atom, a fluorine atom, a chlorine atom, cyano, C ₁ -C ₃ alkoxy or methylthio,
Y ³ is a halogen atom, trifluoromethyl, C ₂ -C ₄ alkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted by R ⁶ , C ₁ -C ₄ haloalkoxy or -C (R ⁸ ) = NOR ⁹
Y ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ Represents -C ₄ haloalkenyl or C ₃ -C ₆ alkynyl,
R ² represents a hydrogen atom or methyl, provided that when G ² represents a structure represented by G ² -1, R ² represents methyl;
R ³ represents a hydrogen atom, or R ³ together with R ² forms an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ² and R ³ are bonded. ,
R ⁴ represents a hydrogen atom, cyclopropyl or methoxy,
R ⁵ represents methyl,
R ⁶ represents a halogen atom, C ₃ -C ₆ cycloalkyl, —OR ⁷ , trimethylsilyl, —C (R ⁸ ) ═NOR ⁹ or phenyl,
R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxymethyl;
R ¹⁰ represents C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, trimethylsilyl, phenyl, phenyl substituted by (Z) _m or D-32;
Z represents a halogen atom or cyano, and when m represents 2 or more, each Z may be the same as or different from each other;
The nematicidal composition according to the above [1], wherein n represents an integer of 1.

[3] G ¹ represents the structure of G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7 or G ¹ -11;
G ² is, represents the structure of G ² -1 or ^{G 2} -2,
X ¹ represents a halogen atom, methyl, difluoromethyl or trifluoromethyl,
X ² represents a hydrogen atom or a fluorine atom,
X ³ represents a hydrogen atom,
X ⁵ represents a hydrogen atom or a fluorine atom,
Y ¹ represents a chlorine atom or a bromine atom,
Y ² represents a hydrogen atom,
Y ³ represents a halogen atom, trifluoromethyl, cyclopropylethynyl or C ₁ -C ₄ haloalkoxy,
Y ⁴ represents a hydrogen atom,
R ¹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl or C ₃ -C ₆ alkenyl substituted by R ¹⁰ ,
R ⁴ represents a hydrogen atom,
R ¹⁰ represents C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl or phenyl substituted by (Z) _m ,
Z represents a halogen atom or cyano, and when m represents 2, each Z may be the same as or different from each other;
m is a nematicide composition according to the above [2], which represents an integer of 1 or 2.

[4] G ¹ represents the structure of G ¹ -1,
X ¹ represents a halogen atom, methyl or trifluoromethyl,
X ² represents a hydrogen atom or a fluorine atom,
X ³ represents a hydrogen atom,
X ⁴ represents a hydrogen atom,
X ⁵ is nematicidal composition according to [3] represents a hydrogen atom or a fluorine atom.
[5] ^{G 1} represents the structure of G ¹ -2,
X ¹ represents a chlorine atom or trifluoromethyl,
X ³ , X ⁴ and X ⁵ are the nematicidal compositions according to the above [3], wherein each represents a hydrogen atom.
[6] G ¹ represents the structure of G ¹ -3,
X ¹ represents a chlorine atom, difluoromethyl or trifluoromethyl,
X ² , X ³ and X ⁴ represent the nematicidal composition according to the above [3], which represents a hydrogen atom.
[7] G ¹ represents the structure of G ¹ -7,
X ¹ represents trifluoromethyl,
X ³ and X ⁴ are the nematicidal compositions according to the above [3], each representing a hydrogen atom.
[8] G ¹ represents the structure of G ¹ -11;
X ¹ represents methyl,
X ³ and X ⁴ are the nematicidal compositions according to the above [3], each representing a hydrogen atom.
[9] ^{G 2} are represent the structure of G ² -2,
Y ¹ represents a chlorine atom or a bromine atom,
Y ² represents a hydrogen atom,
Y ³ represents a fluorine atom, a chlorine atom, a bromine atom, trifluoromethyl, cyclopropylethynyl or C ₁ -C ₄ haloalkoxy.
Y ⁴ are nematicidal composition according to [3] represents a hydrogen atom.

[10] A nematicidal composition comprising a synergistically effective amount of the following active ingredient A and the following active ingredient B:
(1) Active ingredient A: one or more compounds selected from the group consisting of the oxime-substituted amide compound represented by the formula (I) described in [1] above, its N-oxide, and salts thereof .
(2) Active ingredient B: one selected from the group consisting of BI group, B-II group, B-III group, B-IV group, BV group, B-VI group, B-VII group and B-VIII group Or two or more compounds.
BI group: Benomyl, Carbofuran, Chloetocarb, Carbosulfuran, Alanicarb, Aldicarb, Aldoxycarb, Oxamyl, Tile Pate.
Group B-II: diamidafos, phenamifos, phostietane, phosphamidon, imisiaphos, mecalphone.
Group B-III: Kazusafos, Chlorpyrifos, Diclofenthion, Dimethoate, Etoprofos, Fensulfothione, Phosthiazate, Heterophos, Isamidophos, Isazofos, Forate, Phosphocarb, Terbufos, Thionazine, Triazophos.
Group B-IV: disulfide, cyanogen, 1,2 dichloropropane, 1,3 dichloropropene, dithioether, methyl bromide, methyl iodate, tetrathiocarbonite sodium salt.
BV group: Abamectin, Carbachol, Acetoprole, Benclothiaz, Chloropicrin, Daazomet, Divisipi, Disiaipi, Fluenesulfone, Fafural, Metam, Methyl isothiocyanate, Thioxazafen, Xylenols, Triazophos, Sclareol, Chloranthraniprole, Cyantrani Liprol, cyclaniliprol, iprodione, AKD-1193 (trial name).
Group B-VI: Pasteuria bacteria, Pasteuria penetrans, Pasteuria ramosa, Pasteuria solnai, Pasteurian nisawae.
Group B-VII: sulfur, lime sulfur mixture, basic copper sulfate, iprovenfos, edifenphos, toluclofos methyl, thiram, polycarbamate, dinebu, manzeb, mancozeb, propineb, thiophanate, thiophanate methyl, iminoctadine acetate, iminoctadine albe Silates, mepronil, flutolanil, pencyclon, furamethpyr, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanide, fursulfamide, chlorothalonil, cresoxime methyl, phenoxanyl, himexazole, ecromezol, fluorimido, procimidone, vinclozoline, fluclozoline, fludiazol Zole, ipconazole, fluconazole, propiconazole, difenoconazole, microbe Nil, tetraconazole, hexaconazole, tebuconazole, thiazinyl, imibenconazole, prochloraz, pefrazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanyl, mepanipyrim, pyrifenox, fluazinam, trifolin, dichromedin, azoxystrobin, thiadiazine , Captan, probenazole, acibenzoral S methyl, fusaride, tricyclazole, pyroxylone, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin, fluazinam, triclamid, amisulbrom.
Group B-VIII: Sienopyrafen, Ethion, Trichlorfone, Metamidophos, Acephate, Dichlorvos, Mevinfos, Monocrotofos, Malathion, Formothione, Mecarbam, Bamidthione, Thiometone, Disulfotone, Oxydeprophos, Nared, Methylparathion, Fenitrothion, Cyanophos, Propaphos, Fentione Prothiophos, Profenofos, Isophenphos, Temefos, Fentoate, Dimethylvinphos, Chlorfevinphos, Tetrachlorbinphos, Hoxime, Isoxathion, Pyraclofos, Methidathion, Chloropyphos, Pyridaphenthion, Diazinon, Pirimiphosmethyl, Hosalon, Phosmet, Dioxabenzophos, Quinalphos , Mesulfenphos, DPS, isoamidophos, enaprophos, Enthion, Sulprofos, Pyrethrin, Allethrin, Praretrin, Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropatrine, Cypermethrin, Alpha cypermethrin, Cyhalothrin, Lambdacyhalothrin, Deltamethrin, Acrinatrin, Fenvalerate, Esfenvalerate, Cysprovalerate , Etofenprox, halfenprox, silafluophene, flucitrinate, fulvalinate, mesomil, thiodicarb, cartap, metorcarb, xylcarb, propoxyl, phenoxycarb, fenobucarb, etiofencarb, phenothiocarb, bifenazete, BPMC, carbaryl, pyrimibencarb, furathiocarb , Diafenthiuron, difluve Duron, teflubenzuron, hexaflumuuron, novallon, rufenuron, flufenoxuron, chlorfluazuron, fenbutane oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, metoprene, hydroprene, vinapacryl, amitraz, dichor, kelsen , Chlorbenzilate, phenisobromolate, tetradiphone, bensultap, benzomate, tebufenozide, methoxyphenozide, pyridalyl, metaflumizone, flubendiamide, chromafenozide, propargite, acequinosyl, endosulfan, diofenolan, chlorfenapyrazole, fenpyroximate, tolfenpyrazole , Hexythiazox, Nicotine sulfate, nitenpyram, acetamiprid, thiacloprid, imidacloprid, thiamethoxam, clothianidin, dinotefuran, pyriproxyfen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC, pymetrozine, clofentezine, buprofezin, thiocyclam, phenazaquin, indoxameb , Polynactin complex, milbemectin, emamectin benzoate, spinosad, BT, azadirachtin, rotenone, hydroxypropyl starch, levamisole hydrochloride, morantel tartrate, monacrosporium fimatopagum.

[11] The nematicidal composition as described in [10] above, which contains an active ingredient B selected from the BI group.
[12] The nematicidal composition according to the above [10], which comprises an active ingredient B selected from the B-II group.
[13] The nematicidal composition as described in [10] above, which comprises an active ingredient B selected from the B-III group.
[14] The nematicidal composition according to [10] above, which contains an active ingredient B selected from the B-IV group.
[15] The nematicidal composition according to [10] above, which comprises an active ingredient B selected from the BV group.
[16] The nematicidal composition as described in [10] above, which contains an active ingredient B selected from the B-VI group.
[17] The nematicidal composition as described in [10] above, which contains an active ingredient B selected from the B-VII group.
[18] The nematicidal composition as described in [10] above, which comprises an active ingredient B selected from the B-VIII group.
[19] The nematicidal composition according to any one of [1] to [18] above, wherein 0.001 to 1000 parts by weight of the active ingredient B is contained per 1 part by weight of the active ingredient A.

[20] One or more active ingredients A according to [10] above and one or more active ingredients B according to [10] above, or close in time A method for controlling nematodes, characterized by comprising:
[21] A method for controlling nematodes, which comprises treating the nematicidal composition according to any one of [1] to [19] with soil.
[22] The above-mentioned [20] or [21], wherein the treatment amount of the active ingredient A is 0.1 to 1000 ga.i./ha and the treatment amount of the active ingredient B is 0.1 to 1000 ga.i./ha. ] The control method of description.
[23] The control method according to [20] or [21] above, wherein the amount of the applied drug is 0.005 to 50 kg per hectare as the amount of active ingredient.
[24] A method for controlling nematodes, which comprises treating a seed of a plant with the nematicidal composition according to any one of [1] to [19].
[25] A method for controlling nematodes, which comprises treating the nematicidal composition according to any one of [1] to [19] in a nursery box.

The composition of the present invention and the method of the present invention have a low dose and a broad control spectrum against various nematodes. It also has an excellent synergistic control effect against plant growth damage caused by various nematodes and sufficient synergy with nematodes that have acquired resistance to existing nematicides. Demonstrate effective control.

Oxime-substituted amide compound represented by formula (I) [hereinafter abbreviated as compound (I). ], There are geometric isomers of E-form and Z-form, and compound (I) used in the composition of the present invention is E-form, Z-form, or E-form and Z-form. Are included in any proportion.
In Compound (I), depending on the substituent, there may be an optically active substance resulting from the presence of one or more asymmetric carbon atoms, but the compound (I) used in the composition of the present invention ( I) encompasses all optically active or racemic forms.

Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.
The expression “C _a -C _b alkyl” represents a linear or branched hydrocarbon group having a to b carbon atoms, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, Specific examples are butyl group, isobutyl group, s-butyl group, tert-butyl group, pentyl group, 1-ethylpropyl group, 2,2-dimethylpropyl group, hexyl group, etc. The range is selected. Here, sec- means secondary, tert- means tertiary, and the same applies to the following.
The expression “C _a -C _b haloalkyl” is a linear or branched hydrocarbon group having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom In this case, when two or more halogen atoms are substituted, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 1-fluoroethyl group, 2 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2, 2-trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2,2,3,3-tetrafluoropropyl group 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-1- (methyl ) Ethyl group, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3, Specific examples include 4,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group, and the like. Selected by range.
The expression “C _a -C _b cycloalkyl” represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 10 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, cyclobutyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, cyclopentyl group, 2,2-dimethylcyclopropyl group, 1-methylcyclobutyl group, cyclohexyl group and the like. Selected within a range of each specified number of carbon atoms.

The expression “C _a -C _b alkenyl” is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule. Represents a hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 1-butenyl group, 2-butenyl group, 1-methyl-1-propenyl group, 2-methyl-1 Specific examples include -propenyl group, 2-methyl-2-propenyl group, 3-methyl-3-butenyl group and the like, and each is selected within the range of the designated number of carbon atoms.
The notation “C _a -C _b haloalkenyl” is a linear or branched chain consisting of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and Represents an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2-fluorovinyl group, 2-chlorovinyl group, 1,2-dichlorovinyl group, 2,2-dichlorovinyl group, 2,2-dibromovinyl group, 2-fluoro-2-propenyl group, 2-chloro -2-propenyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2, 3,3-trifluoro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 1- (trifluoromethyl) ethenyl group, 4,4-difluoro-3-butenyl group, 3,4, Specific examples include 4-trifluoro-3-butenyl group, 2,4,4,4-tetrafluoro-2-butenyl group, 3-chloro-4,4,4-trifluoro-2-butenyl group, and the like. , Each selected range of carbon atoms.

The expression “C _a -C _b alkynyl” is a linear or branched chain having a carbon number of a to b and an unsaturated carbonization having one or more triple bonds in the molecule. Represents a hydrogen group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 1-pentynyl group, 2 Specific examples include -pentynyl group, 1-hexynyl group, 3-hexynyl group, 3-methyl-1-pentynyl group, 4-methyl-1-pentynyl group, 3,3-dimethyl-1-butynyl group, and the like. Each selected range of carbon atoms is selected.
The notation “C _a -C _b haloalkynyl” is a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom, and Represents an unsaturated hydrocarbon group having one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-fluoro-1-propynyl group, 3-chloro-1-propynyl group, 3-chloro-2-propynyl group, 3-bromo -1-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 3 Specific examples include -bromo-1-butynyl group, 3-fluoro-3-methyl-1-butynyl group, 3-chloro-3-methyl-1-butynyl group, and 3-bromo-3-methyl-1-butynyl group Each selected within a range of each specified number of carbon atoms.

The expression “C _a -C _b alkoxy” represents an alkyl-O— group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group Specific examples include butyloxy group, isobutyloxy group, s-butyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.
The expression “C _a -C _b haloalkoxy” represents a haloalkyl-O— group having the above-mentioned meanings consisting of a to b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group. Group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1, Specific examples include 1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, and the like, which are selected within the range of the respective designated number of carbon atoms.
The expression “C _a -C _b alkylthio” represents an alkyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methylthio group, ethylthio group, propylthio group, isopropylthio group, Specific examples include a butylthio group, an isobutylthio group, an s-butylthio group, a tert-butylthio group, and the like, and each is selected within the range of the designated number of carbon atoms.

The expression “C _a -C _b haloalkylthio” represents a haloalkyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms, such as a difluoromethylthio group, a trifluoromethylthio group, a chlorodifluoromethylthio group. Group, trichloromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethyl group Thio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl ) Ethylthio group, nonafluorobutylthio group, and the like are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
The expression “C _a -C _b alkylsulfinyl” represents an alkyl-S (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methylsulfinyl group, ethylsulfinyl group, propyl Specific examples include a sulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, a s-butylsulfinyl group, a tert-butylsulfinyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
The expression “C _a -C _b alkylsulfonyl” represents an alkyl-S (O) ₂ — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, a methylsulfonyl group, an ethylsulfonyl group, Specific examples include a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a s-butylsulfonyl group, a tert-butylsulfonyl group, and the like, which are selected in the range of each designated number of carbon atoms.

The notation of “tri (C _a -C _b alkyl) silyl” is the same or different from each other, and is substituted by an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms Represents a silyl group, for example, trimethylsilyl group, triethylsilyl group, tri (propyl) silyl group, ethyldimethylsilyl group, propyldimethylsilyl group, butyldimethylsilyl group, isobutyldimethylsilyl group, tert-butyldimethylsilyl group, etc. As an example, each selected range of carbon atoms is selected.
The expression “C _a -C _b alkylcarbonyl” represents an alkyl-C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, such as acetyl, propionyl, butyryl, Specific examples include an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

The expression “C _a -C _b alkoxycarbonyl” represents an alkyl-OC (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl group, propyl Specific examples include an oxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a tert-butoxycarbonyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
The expression “(C _a -C _b ) alkyl substituted by R ¹⁰ ” means the above-mentioned meaning comprising a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R ¹⁰ Each selected from a range of each specified number of carbon atoms.
The notation “hydroxy (C _d -C _e ) cycloalkyl” or “C _a -C _b alkoxy (C _d -C _e ) cycloalkyl” is any C _a -C _b alkoxy group, as defined above, or A cycloalkyl group having the above-mentioned meanings of d to e carbon atoms, wherein a hydrogen atom bonded to a carbon atom is optionally substituted by a hydroxyl group, is selected within the range of each designated number of carbon atoms. The
The expression “(C _a -C _b ) alkynyl substituted by R ⁶ ” means the above-mentioned meaning comprising a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is substituted by any R ⁶ Are selected within the range of each specified number of carbon atoms.

In compound (I), examples of the preferred range of the substituent represented by G ^1, for example, G ¹ -I ~ G ¹ -XVI groups below.
That is, G ¹ -I: G ¹ -1 [where X ¹ represents a halogen atom, methyl or trifluoromethyl, X ² represents a hydrogen atom or a fluorine atom, and X ³ and X ⁴ represent a hydrogen atom. , X ⁵ represents a hydrogen atom or a fluorine atom. ].
G ¹ -II: G ¹ -2 [wherein X ¹ represents a chlorine atom or trifluoromethyl, and X ³ , X ⁴ and X ⁵ represent a hydrogen atom. ].
G ¹ -III: G ¹ -3 [wherein X ¹ represents a chlorine atom, difluoromethyl or trifluoromethyl, and X ² , X ³ and X ⁴ represent a hydrogen atom. ].
G ¹ -IV: G ¹ -7 [where X ¹ represents trifluoromethyl, and X ³ and X ⁴ represent a hydrogen atom. ].
G ¹ -V: G ¹ -11 [where X ¹ represents methyl, and X ³ and X ⁴ represent a hydrogen atom. ].
G ¹ -VI: G ¹ -1 [where X ¹ represents nitro and X ² , X ³ , X ⁴ and X ⁵ represent hydrogen atoms. ].
G ¹ -VII: G ¹ -1 [wherein X ¹ represents a halogen atom, methyl or trifluoromethyl, X ² represents a chlorine atom, and X ³ , X ⁴ and X ⁵ represent a hydrogen atom. ].
G ¹ -VIII: G ¹ -1 [where X ¹ represents a halogen atom, methyl or trifluoromethyl, X ² , X ³ and X ⁴ represent a hydrogen atom, and X ⁵ represents a chlorine atom. ].

G ¹ -IX: G ¹ -2 [where X ¹ represents a bromine atom or difluoromethyl, and X ³ , X ⁴ and X ⁵ represent a hydrogen atom. ].
G ¹ -X: G ¹ -7 [where X ¹ represents a chlorine atom or difluoromethyl, and X ³ and X ⁴ represent a hydrogen atom. ].
G ¹ -XI: G ¹ -11 [wherein X ¹ represents a halogen atom, difluoromethyl or trifluoromethyl, and X ³ and X ⁴ represent a hydrogen atom. ].
G ¹ -XII: G ¹ -12 [where X ¹ represents a halogen atom, methyl, difluoromethyl or trifluoromethyl, and X ² and X ³ represent a hydrogen atom. ].
G ¹ -XIII: G ¹ -16 [where X ¹ represents difluoromethyl or trifluoromethyl, X ² and X ⁴ represent a hydrogen atom, and R ⁵ represents methyl. ].
G ¹ -XIV: G ¹ -27 [where X ¹ represents difluoromethyl or trifluoromethyl, X ² represents a hydrogen atom, and R ⁵ represents methyl. ].
G ¹ -XV: G ¹ -27 [where X ¹ represents methyl or trifluoromethyl, X ² represents a fluorine atom or a chlorine atom, and R ⁵ represents methyl. ].
G ¹ -XVI: G ¹ -33 [where X ¹ represents difluoromethyl or trifluoromethyl, and X ³ represents methyl. ].
Among them, as the range of the substituent of G ^1, and more preferably G ¹ -I ~ G ¹ -V or G ¹ -IX ~ G ¹ -XII, the G ¹ -I ~ G ¹ -V Particularly preferred.

In the compound (I), the preferred range of the substituent represented by G ² includes, for example, the following groups G ² -I to G ² -VII.
That is, G ² -I: G ² -1 [where Y ¹ represents a chlorine atom, Y ² represents a hydrogen atom, Y ³ represents a halogen atom, and Y ⁴ and Y ⁵ represent a hydrogen atom. ].
G ² -II: G ² -2 [where Y ¹ represents a chlorine atom or bromine atom, Y ² represents a hydrogen atom, Y ³ represents a fluorine atom, a chlorine atom, a bromine atom, trifluoromethyl, cyclopropyl. It represents ethynyl or C ₁ -C ₄ haloalkoxy, and Y ⁴ represents a hydrogen atom. ].
G ² -III: G ² -1 [where Y ¹ represents a fluorine atom or a bromine atom, Y ² represents a hydrogen atom, Y ³ represents a halogen atom, and Y ⁴ and Y ⁵ represent a hydrogen atom. . ].
G ² -IV: G ² -2 [wherein Y ¹ represents a chlorine atom, Y ² represents a hydrogen atom, Y ³ represents C ₂ -C ₄ alkenyl, C ₂ -C ₆ alkynyl, optionally selected by R ⁶ Represents (C ₂ -C ₆ ) alkynyl or —C (R ⁸ ) ═NOR ⁹ substituted with Y ⁴ represents a hydrogen atom, R ⁶ represents a halogen atom, C ₃ to C ₆ cycloalkyl, —OR ⁷ , Trimethylsilyl, -C (R ⁸ ) = NOR ⁹ or phenyl, R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxymethyl, R ⁸ represents a hydrogen atom or methyl, and R ⁹ represents Represents methyl or ethyl. ].

G ² -V: G ² -2 [where Y ¹ represents a chlorine atom or a bromine atom, Y ² represents a fluorine atom, a chlorine atom, cyano, C ₁ to C ₃ alkoxy or methylthio, and Y ³ represents chlorine An atom or a bromine atom is represented, and Y ⁴ represents a hydrogen atom. ].
G ² -VI: G ² -2 [wherein Y ¹ represents a chlorine atom or a bromine atom, Y ² represents a hydrogen atom, Y ³ represents a halogen atom, trifluoromethyl, cyclopropylethynyl or C ₁ -C ₄ represents haloalkoxy, and Y ⁴ represents a fluorine atom or a chlorine atom. ].
G ² -VII: G ² -9 [wherein Y ¹ represents a chlorine atom or a bromine atom, Y ² represents a hydrogen atom or a chlorine atom, and Y ³ represents a chlorine atom or a bromine atom. ].
Among them, as the range of the substituent of G ^2, G ² -I or G ² -II is particularly preferred.
In compound (I), examples of the substituent represented by W include an oxygen atom or a sulfur atom, and W is more preferably an oxygen atom.

In the compound (I), the preferred range of the substituent represented by R ¹ includes, for example, the following groups R ¹ -I to R ¹ -VIII.
That is, R ¹ -I: (C ₁ -C ₄ ) alkyl substituted by C ₁ -C ₄ alkyl and R ¹⁰ [wherein R ¹⁰ represents C ₃ -C ₆ cycloalkyl. ].
R ¹ -II: C ₁ -C ₄ haloalkyl and (C ₁ -C ₄ ) alkyl substituted by R ¹⁰ [wherein R ¹⁰ represents C ₃ -C ₆ halocycloalkyl. ].
R ¹ -III: C ₃ -C ₆ alkenyl.
R ¹ -IV: substituted by _{^{R 10 (C 1 ~ C 4}} ) alkyl [wherein, R ¹⁰ represents phenyl substituted by (Z) _m, Z represents a halogen atom or a cyano, m is 2 , Each Z may be the same as or different from each other, and m represents 1 or 2. ].
R ¹ -V: C ₁ -C ₆ alkyl and C ₃ -C ₆ cycloalkyl.
R ¹ -VI: (C ₁ -C ₄ ) alkyl substituted by R ¹⁰ [wherein R ¹⁰ represents trimethylsilyl. ].
R ¹ -VII: C ₃ -C ₄ haloalkenyl and C ₃ -C ₆ alkynyl.
R ¹ -VIII: (C ₁ -C ₄ ) alkyl substituted by R ¹⁰ [wherein R ¹⁰ represents phenyl, phenyl substituted by (Z) _m or D-32, Z represents a halogen atom or cyano In the case where m represents 2 or more, each Z may be the same as or different from each other, m represents 3, and n represents 1. ].
Among them, as the range of the substituent of ^{R 1, R 1 -I ~ R} 1 -IV it is particularly preferred.

In the compound (I), examples of combinations of preferable ranges of the substituents represented by R ² and R ³ include the following groups of RI to R-III.
That is, RI: R ² and R ³ are hydrogen atoms.
R-II: R ² is methyl and R ³ is a hydrogen atom.
R-III: R ² and R ³ together form an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ¹ and R ² are bonded.
Of these, RI or R-II is particularly preferred as the combination of the ranges of substituents represented by R ² and R ³ .
In the compound (I), the preferred range of the substituent represented by R ⁴ includes, for example, the following groups of R ⁴ -I to R ⁴ -III.
That is, R ⁴ -I: a hydrogen atom.
R ⁴ -II: cyclopropyl.
R ⁴ -III: Methoxy.
Among them, as the range of the substituent of R ^4, R ⁴ -I it is particularly preferred.
Each group which shows the preferable range of each substituent in compound (I) can be combined arbitrarily, respectively, and represents the preferable range of compound (I).

The compound (I) used in the composition of the present invention is a known compound described in International Patent Application Publication (WO2014 / 010737). For example, compounds having the structural formulas [I] -1 to [I] -36 shown below Is mentioned. However, the compounds of the structural formulas [I] -1 to [I] -36 are for illustration, and the compound (I) used in the composition of the present invention is not limited thereto. .

Here, the substituent G ² in the structural formulas [I] -1 to [I] -36 represents a structure represented by the following G ² -1, G ² -2, or G ² -9, respectively.

Examples of specific combinations of substituents represented by Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ , R ¹ , R ² and R ³ in the above structural formula include, for example, Table 1 The combination shown is mentioned. However, the combinations in Table 1 are for illustration, and the substitutions represented by Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ , R ¹ , R ² and R ³ of compound (I) Specific combinations of groups are not limited to these.

In the table, the substituent described as Et represents an ethyl group. Hereinafter, n-Pr represents a normal propyl group, iP represents an isopropyl group, Pr-c represents a cyclopropyl group, and n-Bu represents a normal butyl group. , S-Bu represents a secondary butyl group, c-Bu and Bu-c represent a cyclobutyl group, Pen represents a pentyl group, and Ph represents a phenyl group.
In the table, the description of T-1 represents the following structure.

In the table, the notation “-” in the column of substituents Y ⁴ and Y ⁵ indicates that there is no corresponding substituent.
The notation of (S) in the column of substituent R ² represents that the (S) -form is 90% or more in the mixing ratio of the optical isomers of the carbon atom to which R ² is bonded.
The description of the column of the substituent R ¹ (E) and (Z), the mixing ratio of the oxime geometric isomers substituents R ¹ are bonded, respectively (E) - form and (Z) - the body 90% It represents that.
These descriptions are the same in the following tables.

Examples of the known nematicide used as the active ingredient B of the present invention include compounds selected from the following groups BI to B-VI.

Active ingredient BI group;
[Table 2]
――――――――――――――――――
NO. Compound name (generic name)
――――――――――――――――――
A01 benomyl
A02 Carbofuran
A03 Cloethocarb
A04 Carbosulfan
A05 Alanicarb
A06 Aldicarb
A07 Aldoxycarb
A08 Oxamyl
A09 tilepate (tirpate)
―――――――――――――――――――

Active ingredient group B-II;
[Table 3]
―――――――――――――――――――――――――
NO. Compound name (generic name)
―――――――――――――――――――――――――
B01 Diamidafos
B02 Fenamiphos
B03 Fosthietan
B04 Phosphamidon
B05 Imiciafos
B06 mecarphon
――――――――――――――――――――――――――

Active ingredient group B-III;
[Table 4]
―――――――――――――――――――――――――――
NO. Compound name (generic name)
―――――――――――――――――――――――――――
C01 cadusafos
C02 Chlorpyrifos
C03 dichlofenthion
C04 Dimethoate
C05 Etoprophos
C06 Fensulfothion
C07 Fosthiazate
C08 heterophos
C09 isamidofos
C10 isazofos
C11 phorate
C12 Phosphocarb
C13 terbufos
C14 Thionazin
C15 triazophos
―――――――――――――――――――――――――――

Active ingredient B-IV group;
[Table 5]
――――――――――――――――――――――――――――――――――
NO. Compound name (generic name)
――――――――――――――――――――――――――――――――――
D01 carbon disulfide
D02 Cyanogen
D03 1,2-dichloropropane
D04 1,3-dichloropropene
D05 dithioether
D06 Methyl bromide
D07 Methyl iodide
D08 Tetrathiocarbonite sodium tetrathiocarbonate
――――――――――――――――――――――――――――――――――

Active ingredient BV group;
[Table 6]
―――――――――――――――――――――――――――
NO. Compound name (generic name)
―――――――――――――――――――――――――――
E01 Abamectin
E02 Carvacol
E03 Acetoprole
E04 Benclothiaz
E05 Chloropicrin
E06 dazomet
E07 Divisipi (DBCP)
E08 DISIP (DCIP)
E09 fluensulfone
E10 furfural
E11 metam
E12 methyl isothiocyanate
E13 tioxazafen
E14 xylenols
E15 triazophos
E16 sclareol
E17 Chlorantraniliprole
E18 Cyantraniliprole
E19 Cyclaniliprole
E20 iprodione

E21 AKD-1193 Exam Name ――――――――――――――――――――――――――――
Active ingredient B-VI group;
[Table 7]
―――――――――――――――――――――――――――
NO. Compound name (generic name)
―――――――――――――――――――――――――――
F01 Pasturia
F02 Pasturia penetrans
F03 Pasturia ramose
F04 Pasturia thornei
F05 Pasturia nishizawae
―――――――――――――――――――――――――――

Next, examples of combinations of [active ingredient A] selected from the compound (I) having a synergistic disease control effect and [active ingredient B] selected from known nematicides are listed below. In the following notation, for example, the notation “1 + A01” indicates that the active ingredient A is the No. 1 compound in Table 2 and the active ingredient B is the benomyl in No. A01 in Table 4. Represents a combination.
Examples of compound combinations: “1+ (A01)”, “1+ (A02)”, “1+ (A03)”, “1+ (A04)”, “1+ (A05)”, “1+ ( A06), 1+ (A07), 1+ (A08), 1+ (A09), 1+ (B01), 1+ (B02), 1+ (B03) ”,“ 1+ (B04) ”,“ 1+ (B05) ”,“ 1+ (B06) ”,“ 1+ (C01) ”,“ 1+ (C02) ”,“ 1+ (C03) ”, 1+ (C04), 1+ (C05), 1+ (C06), 1+ (C07), 1+ (C08), 1+ (C09), 1 + (C10), 1+ (C11), 1+ (C12), 1+ (C13), 1+ (C14), 1+ (C15), 1+ ( D01), 1+ (D02), 1+ (D03), 1+ (D04), 1+ (D05), 1+ (D06), 1+ (D07) , 1+ (D08), 1+ (E01), 1+ (E02), 1+ (E03), 1+ (E04), 1+ (E05), 1+ (E06), 1+ (E07), 1+ (E08), 1+ (E09), 1+ (E10), 1+ (E11), 1 + (E12), 1+ (E13), 1+ (E14), 1+ (E15), 1+ (E16), 1+ (E17), 1+ ( E18), 1+ (E19), 1+ (E20), 1+ (E21), 1+ (F01), 1 + (F02), 1+ (F03), 1+ (F04), 1+ (F05)
`` 2+ (A01) '', `` 2+ (A02) '', `` 2+ (A03) '', `` 2+ (A04) '', `` 2+ (A05) '', `` 2+ (A06) '', `` 2 + (A07), 2+ (A08), 2+ (A09), 2+ (B01), 2+ (B02), 2+ (B03), 2+ ( B04), 2+ (B05), 2+ (B06), 2+ (C01), 2+ (C02), 2+ (C03), 2+ (C04) , 2+ (C05), 2+ (C06), 2+ (C07), 2+ (C08), 2+ (C09), 2+ (C10), `` 2+ (C11) '', `` 2+ (C12) '', `` 2+ (C13) '', `` 2+ (C14) '', `` 2+ (C15) '', `` 2+ (D01) '', `` 2 + (D02), 2+ (D03), 2+ (D04), 2+ (D05), 2+ (D06), 2+ (D07), 2+ ( D08), 2+ (E01), 2+ (E02), 2+ (E03), 2+ (E04), 2+ (E05), 2+ (E06) , 2+ (E07), 2+ (E08), 2+ (E09), 2+ (E10), 2+ (E11), 2+ (E12), `` 2+ (E13) '', `` 2+ (E14) '', `` 2+ (E15) '', `` 2+ (E16) '', `` 2+ (E17) '', `` 2+ (E18) '', `` 2 + (E19), 2+ (E20), 2+ (E21), 2+ (F01), 2+ (F02), 2+ (F03), 2+ ( F0 4) "," 2+ (F05) ".
3+ (A01), 3+ (A02), 3+ (A03), 3+ (A04), 3+ (A05), 3+ (A06), 3 + (A07), 3+ (A08), 3+ (A09), 3+ (B01), 3+ (B02), 3+ (B03), 3+ ( B04), 3+ (B05), 3+ (B06), 3+ (C01), 3+ (C02), 3+ (C03), 3+ (C04) , 3+ (C05), 3+ (C06), 3+ (C07), 3+ (C08), 3+ (C09), 3+ (C10), 3+ (C11), 3+ (C12), 3+ (C13), 3+ (C14), 3+ (C15), 3+ (D01), 3 + (D02), 3+ (D03), 3+ (D04), 3+ (D05), 3+ (D06), 3+ (D07), 3+ ( D08), 3+ (E01), 3+ (E02), 3+ (E03), 3+ (E04), 3+ (E05), 3+ (E06) , 3+ (E07), 3+ (E08), 3+ (E09), 3+ (E10), 3+ (E11), 3+ (E12), 3+ (E13), 3+ (E14), 3+ (E15), 3+ (E16), 3+ (E17), 3+ (E18), 3 + (E19), 3+ (E20), 3+ (E21), 3+ (F01), 3+ (F02), 3+ (F03), 3+ ( F0 4) "," 3+ (F05) ".
4+ (A01), 4+ (A02), 4+ (A03), 4+ (A04), 4+ (A05), 4+ (A06), 4 + (A07), 4+ (A08), 4+ (A09), 4+ (B01), 4+ (B02), 4+ (B03), 4+ ( B04), 4+ (B05), 4+ (B06), 4+ (C01), 4+ (C02), 4+ (C03), 4+ (C04) , 4+ (C05), 4+ (C06), 4+ (C07), 4+ (C08), 4+ (C09), 4+ (C10), 4+ (C11), 4+ (C12), 4+ (C13), 4+ (C14), 4+ (C15), 4+ (D01), 4 + (D02), 4+ (D03), 4+ (D04), 4+ (D05), 4+ (D06), 4+ (D07), 4+ ( D08), 4+ (E01), 4+ (E02), 4+ (E03), 4+ (E04), 4+ (E05), 4+ (E06) , 4+ (E07), 4+ (E08), 4+ (E09), 4+ (E10), 4+ (E11), 4+ (E12), 4+ (E13), 4+ (E14), 4+ (E15), 4+ (E16), 4+ (E17), 4+ (E18), 4 + (E19), 4+ (E20), 4+ (E21), 4+ (F01), 4+ (F02), 4+ (F03), 4+ ( F0 4) "," 4+ (F05) ".
5+ (A01), 5+ (A02), 5+ (A03), 5+ (A04), 5+ (A05), 5+ (A06), 5 + (A07), 5+ (A08), 5+ (A09), 5+ (B01), 5+ (B02), 5+ (B03), 5+ ( B04), 5+ (B05), 5+ (B06), 5+ (C01), 5+ (C02), 5+ (C03), 5+ (C04) ”,“ 5+ (C05) ”,“ 5+ (C06) ”,“ 5+ (C07) ”,“ 5+ (C08) ”,“ 5+ (C09) ”,“ 5+ (C10) ”, 5+ (C11), 5+ (C12), 5+ (C13), 5+ (C14), 5+ (C15), 5+ (D01), 5 + (D02), 5+ (D03), 5+ (D04), 5+ (D05), 5+ (D06), 5+ (D07), 5+ ( D08), 5+ (E01), 5+ (E02), 5+ (E03), 5+ (E04), 5+ (E05), 5+ (E06) , 5+ (E07), 5+ (E08), 5+ (E09), 5+ (E10), 5+ (E11), 5+ (E12), 5+ (E13), 5+ (E14), 5+ (E15), 5+ (E16), 5+ (E17), 5+ (E18), 5 + (E19), 5+ (E20), 5+ (E21), 5+ (F01), 5+ (F02), 5+ (F03), 5+ ( F0 4) "," 5+ (F05) ".
6+ (A01), 6+ (A02), 6+ (A03), 6+ (A04), 6+ (A05), 6+ (A06), 6 + (A07), 6+ (A08), 6+ (A09), 6+ (B01), 6+ (B02), 6+ (B03), 6+ ( B04), 6+ (B05), 6+ (B06), 6+ (C01), 6+ (C02), 6+ (C03), 6+ (C04) ”,“ 6+ (C05) ”,“ 6+ (C06) ”,“ 6+ (C07) ”,“ 6+ (C08) ”,“ 6+ (C09) ”,“ 6+ (C10) ”, 6+ (C11), 6+ (C12), 6+ (C13), 6+ (C14), 6+ (C15), 6+ (D01), 6 + (D02), 6+ (D03), 6+ (D04), 6+ (D05), 6+ (D06), 6+ (D07), 6+ ( D08), 6+ (E01), 6+ (E02), 6+ (E03), 6+ (E04), 6+ (E05), 6+ (E06) , 6+ (E07), 6+ (E08), 6+ (E09), 6+ (E10), 6+ (E11), 6+ (E12), 6+ (E13), 6+ (E14), 6+ (E15), 6+ (E16), 6+ (E17), 6+ (E18), 6 + (E19), 6+ (E20), 6+ (E21), 6+ (F01), 6+ (F02), 6+ (F03), 6+ ( F0 4) "," 6+ (F05) ".

7+ (A01), 7+ (A02), 7+ (A03), 7+ (A04), 7+ (A05), 7+ (A06), 7 + (A07), 7+ (A08), 7+ (A09), 7+ (B01), 7+ (B02), 7+ (B03), 7+ ( B04), 7+ (B05), 7+ (B06), 7+ (C01), 7+ (C02), 7+ (C03), 7+ (C04) , 7+ (C05), 7+ (C06), 7+ (C07), 7+ (C08), 7+ (C09), 7+ (C10), 7+ (C11), 7+ (C12), 7+ (C13), 7+ (C14), 7+ (C15), 7+ (D01), 7 + (D02), 7+ (D03), 7+ (D04), 7+ (D05), 7+ (D06), 7+ (D07), 7+ ( D08), 7+ (E01), 7+ (E02), 7+ (E03), 7+ (E04), 7+ (E05), 7+ (E06) , 7+ (E07), 7+ (E08), 7+ (E09), 7+ (E10), 7+ (E11), 7+ (E12), 7+ (E13), 7+ (E14), 7+ (E15), 7+ (E16), 7+ (E17), 7+ (E18), 7 + (E19), 7+ (E20), 7+ (E21), 7+ (F01), 7+ (F02), 7+ (F03), 7+ ( F0 4) "," 7+ (F05) ".
8+ (A01), 8+ (A02), 8+ (A03), 8+ (A04), 8+ (A05), 8+ (A06), 8 + (A07), 8+ (A08), 8+ (A09), 8+ (B01), 8+ (B02), 8+ (B03), 8+ ( B04), 8+ (B05), 8+ (B06), 8+ (C01), 8+ (C02), 8+ (C03), 8+ (C04) "," 8+ (C05) "," 8+ (C06) "," 8+ (C07) "," 8+ (C08) "," 8+ (C09) "," 8+ (C10) ", 8+ (C11), 8+ (C12), 8+ (C13), 8+ (C14), 8+ (C15), 8+ (D01), 8 + (D02), 8+ (D03), 8+ (D04), 8+ (D05), 8+ (D06), 8+ (D07), 8+ ( D08), 8+ (E01), 8+ (E02), 8+ (E03), 8+ (E04), 8+ (E05), 8+ (E06) "," 8+ (E07) "," 8+ (E08) "," 8+ (E09) "," 8+ (E10) "," 8+ (E11) "," 8+ (E12) ", 8+ (E13), 8+ (E14), 8+ (E15), 8+ (E16), 8+ (E17), 8+ (E18), 8 + (E19), 8+ (E20), 8+ (E21), 8+ (F01), 8+ (F02), 8+ (F03), 8+ ( F0 4) "," 8+ (F05) ".
“9+ (A01)”, “9+ (A02)”, “9+ (A03)”, “9+ (A04)”, “9+ (A05)”, “9+ (A06)”, “9 + (A07), 9+ (A08), 9+ (A09), 9+ (B01), 9+ (B02), 9+ (B03), 9+ ( B04), 9+ (B05), 9+ (B06), 9+ (C01), 9+ (C02), 9+ (C03), 9+ (C04) ”,“ 9+ (C05) ”,“ 9+ (C06) ”,“ 9+ (C07) ”,“ 9+ (C08) ”,“ 9+ (C09) ”,“ 9+ (C10) ”, 9+ (C11), 9+ (C12), 9+ (C13), 9+ (C14), 9+ (C15), 9+ (D01), 9 + (D02), 9+ (D03), 9+ (D04), 9+ (D05), 9+ (D06), 9+ (D07), 9+ ( D08), 9+ (E01), 9+ (E02), 9+ (E03), 9+ (E04), 9+ (E05), 9+ (E06) , 9+ (E07), 9+ (E08), 9+ (E09), 9+ (E10), 9+ (E11), 9+ (E12), 9+ (E13), 9+ (E14), 9+ (E15), 9+ (E16), 9+ (E17), 9+ (E18), 9 + (E19), 9+ (E20), 9+ (E21), 9+ (F01), 9+ (F02), 9+ (F03), 9+ ( F0 4) "," 9+ (F05) ".
10+ (A01), 10+ (A02), 10+ (A03), 10+ (A04), 10+ (A05), 10+ (A06), 10 + (A07), 10+ (A08), 10+ (A09), 10+ (B01), 10+ (B02), 10+ (B03), 10+ ( B04), 10+ (B05), 10+ (B06), 10+ (C01), 10+ (C02), 10+ (C03), 10+ (C04) ”,“ 10+ (C05) ”,“ 10+ (C06) ”,“ 10+ (C07) ”,“ 10+ (C08) ”,“ 10+ (C09) ”,“ 10+ (C10) ”, 10+ (C11), 10+ (C12), 10+ (C13), 10+ (C14), 10+ (C15), 10+ (D01), 10 + (D02), 10+ (D03), 10+ (D04), 10+ (D05), 10+ (D06), 10+ (D07), 10+ ( D08), 10+ (E01), 10+ (E02), 10+ (E03), 10+ (E04), 10+ (E05), 10+ (E06) ”,“ 10+ (E07) ”,“ 10+ (E08) ”,“ 10+ (E09) ”,“ 10+ (E10) ”,“ 10+ (E11) ”,“ 10+ (E12) ”, 10+ (E13), 10+ (E14), 10+ (E15), 10+ (E16), 10+ (E17), 10+ (E18), 10 + (E19), 10+ (E20), 10+ (E21) , “10+ (F01)”, “10+ (F02)”, “10+ (F03)”, “10+ (F04)”, “10+ (F05)”.
11+ (A01), 11+ (A02), 11+ (A03), 11+ (A04), 11+ (A05), 11+ (A06), 11 + (A07), 11+ (A08), 11+ (A09), 11+ (B01), 11+ (B02), 11+ (B03), 11+ ( B04), 11+ (B05), 11+ (B06), 11+ (C01), 11+ (C02), 11+ (C03), 11+ (C04) ”,“ 11+ (C05) ”,“ 11+ (C06) ”,“ 11+ (C07) ”,“ 11+ (C08) ”,“ 11+ (C09) ”,“ 11+ (C10) ”, 11+ (C11), 11+ (C12), 11+ (C13), 11+ (C14), 11+ (C15), 11+ (D01), 11 + (D02), 11+ (D03), 11+ (D04), 11+ (D05), 11+ (D06), 11+ (D07), 11+ ( D08), 11+ (E01), 11+ (E02), 11+ (E03), 11+ (E04), 11+ (E05), 11+ (E06) ”,“ 11+ (E07) ”,“ 11+ (E08) ”,“ 11+ (E09) ”,“ 11+ (E10) ”,“ 11+ (E11) ”,“ 11+ (E12) ”, 11+ (E13), 11+ (E14), 11+ (E15), 11+ (E16), 11+ (E17), 11+ (E18), 11 + (E19), 11 + (E20), 11 + (E21) , “11+ (F01)”, “11+ (F02)”, “11+ (F03)”, “11+ (F04)”, “11+ (F05)”.
12+ (A01), 12+ (A02), 12+ (A03), 12+ (A04), 12+ (A05), 12+ (A06), 12 + (A07), 12+ (A08), 12+ (A09), 12+ (B01), 12+ (B02), 12+ (B03), 12+ ( B04), 12+ (B05), 12+ (B06), 12+ (C01), 12+ (C02), 12+ (C03), 12+ (C04) ”,“ 12+ (C05) ”,“ 12+ (C06) ”,“ 12+ (C07) ”,“ 12+ (C08) ”,“ 12+ (C09) ”,“ 12+ (C10) ”, 12+ (C11), 12+ (C12), 12+ (C13), 12+ (C14), 12+ (C15), 12+ (D01), 12 + (D02), 12+ (D03), 12+ (D04), 12+ (D05), 12+ (D06), 12+ (D07), 12+ ( D08), 12+ (E01), 12+ (E02), 12+ (E03), 12+ (E04), 12+ (E05), 12+ (E06) ”,“ 12+ (E07) ”,“ 12+ (E08) ”,“ 12+ (E09) ”,“ 12+ (E10) ”,“ 12+ (E11) ”,“ 12+ (E12) ”, 12+ (E13), 12+ (E14), 12+ (E15), 12+ (E16), 12+ (E17), 12+ (E18), 12 + (E19) '', `` 12+ (E20) '', `` 12+ (E21) '' , “12+ (F01)”, “12+ (F02)”, “12+ (F03)”, “12+ (F04)”, “12+ (F05)”.
13+ (A01), 13+ (A02), 13+ (A03), 13+ (A04), 13+ (A05), 13+ (A06), 13 + (A07), 13+ (A08), 13+ (A09), 13+ (B01), 13+ (B02), 13+ (B03), 13+ ( B04), 13+ (B05), 13+ (B06), 13+ (C01), 13+ (C02), 13+ (C03), 13+ (C04) ”,“ 13+ (C05) ”,“ 13+ (C06) ”,“ 13+ (C07) ”,“ 13+ (C08) ”,“ 13+ (C09) ”,“ 13+ (C10) ”, 13+ (C11), 13+ (C12), 13+ (C13), 13+ (C14), 13+ (C15), 13+ (D01), 13 + (D02), 13+ (D03), 13+ (D04), 13+ (D05), 13+ (D06), 13+ (D07), 13+ ( D08), 13+ (E01), 13+ (E02), 13+ (E03), 13+ (E04), 13+ (E05), 13+ (E06) ”,“ 13+ (E07) ”,“ 13+ (E08) ”,“ 13+ (E09) ”,“ 13+ (E10) ”,“ 13+ (E11) ”,“ 13+ (E12) ”, 13+ (E13), 13+ (E14), 13+ (E15), 13+ (E16), 13+ (E17), 13+ (E18), 13 + (E19), 13 + (E20), 13 + (E21) , “13+ (F01)”, “13+ (F02)”, “13+ (F03)”, “13+ (F04)”, “13+ (F05)”.
14+ (A01), 14+ (A02), 14+ (A03), 14+ (A04), 14+ (A05), 14+ (A06), 14 + (A07), 14+ (A08), 14+ (A09), 14+ (B01), 14+ (B02), 14+ (B03), 14+ ( B04), 14+ (B05), 14+ (B06), 14+ (C01), 14+ (C02), 14+ (C03), 14+ (C04) ”,“ 14+ (C05) ”,“ 14+ (C06) ”,“ 14+ (C07) ”,“ 14+ (C08) ”,“ 14+ (C09) ”,“ 14+ (C10) ”, 14+ (C11), 14+ (C12), 14+ (C13), 14+ (C14), 14+ (C15), 14+ (D01), 14 + (D02), 14+ (D03), 14+ (D04), 14+ (D05), 14+ (D06), 14+ (D07), 14+ ( D08), 14+ (E01), 14+ (E02), 14+ (E03), 14+ (E04), 14+ (E05), 14+ (E06) , 14+ (E07), 14+ (E08), 14+ (E09), 14+ (E10), 14+ (E11), 14+ (E12), 14+ (E13), 14+ (E14), 14+ (E15), 14+ (E16), 14+ (E17), 14+ (E18), 14 + (E19), 14 + (E20), 14 + (E21) , “14+ (F01)”, “14+ (F02)”, “14+ (F03)”, “14+ (F04)”, “14+ (F05)”.
15+ (A01), 15+ (A02), 15+ (A03), 15+ (A04), 15+ (A05), 15+ (A06), 15 + (A07), 15+ (A08), 15+ (A09), 15+ (B01), 15+ (B02), 15+ (B03), 15+ ( B04), 15+ (B05), 15+ (B06), 15+ (C01), 15+ (C02), 15+ (C03), 15+ (C04) ”,“ 15+ (C05) ”,“ 15+ (C06) ”,“ 15+ (C07) ”,“ 15+ (C08) ”,“ 15+ (C09) ”,“ 15+ (C10) ”, 15+ (C11), 15+ (C12), 15+ (C13), 15+ (C14), 15+ (C15), 15+ (D01), 15 + (D02), 15+ (D03), 15+ (D04), 15+ (D05), 15+ (D06), 15+ (D07), 15+ ( D08), 15+ (E01), 15+ (E02), 15+ (E03), 15+ (E04), 15+ (E05), 15+ (E06) ”,“ 15+ (E07) ”,“ 15+ (E08) ”,“ 15+ (E09) ”,“ 15+ (E10) ”,“ 15+ (E11) ”,“ 15+ (E12) ”, 15+ (E13), 15+ (E14), 15+ (E15), 15+ (E16), 15+ (E17), 15+ (E18), 15 + (E19), 15+ (E20), 15+ (E21) , “15+ (F01)”, “15+ (F02)”, “15+ (F03)”, “15+ (F04)”, “15+ (F05)”.

16+ (A01), 16+ (A02), 16+ (A03), 16+ (A04), 16+ (A05), 16+ (A06), 16 + (A07), 16+ (A08), 16+ (A09), 16+ (B01), 16+ (B02), 16+ (B03), 16+ ( B04), 16+ (B05), 16+ (B06), 16+ (C01), 16+ (C02), 16+ (C03), 16+ (C04) , 16+ (C05), 16+ (C06), 16+ (C07), 16+ (C08), 16+ (C09), 16+ (C10), 16+ (C11), 16+ (C12), 16+ (C13), 16+ (C14), 16+ (C15), 16+ (D01), 16 + (D02), 16+ (D03), 16+ (D04), 16+ (D05), 16+ (D06), 16+ (D07), 16+ ( D08), 16+ (E01), 16+ (E02), 16+ (E03), 16+ (E04), 16+ (E05), 16+ (E06) , 16+ (E07), 16+ (E08), 16+ (E09), 16+ (E10), 16+ (E11), 16+ (E12), 16+ (E13), 16+ (E14), 16+ (E15), 16+ (E16), 16+ (E17), 16+ (E18), 16 + (E19), 16+ (E20), 16+ (E21) , “16+ (F01)”, “16+ (F02)”, “16+ (F03)”, “16+ (F04)”, “16+ (F05)”.
17+ (A01), 17+ (A02), 17+ (A03), 17+ (A04), 17+ (A05), 17+ (A06), 17 + (A07), 17+ (A08), 17+ (A09), 17+ (B01), 17+ (B02), 17+ (B03), 17+ ( B04), 17+ (B05), 17+ (B06), 17+ (C01), 17+ (C02), 17+ (C03), 17+ (C04) ”,“ 17+ (C05) ”,“ 17+ (C06) ”,“ 17+ (C07) ”,“ 17+ (C08) ”,“ 17+ (C09) ”,“ 17+ (C10) ”, 17+ (C11), 17+ (C12), 17+ (C13), 17+ (C14), 17+ (C15), 17+ (D01), 17 + (D02), 17+ (D03), 17+ (D04), 17+ (D05), 17+ (D06), 17+ (D07), 17+ ( D08), 17+ (E01), 17+ (E02), 17+ (E03), 17+ (E04), 17+ (E05), 17+ (E06) , 17+ (E07), 17+ (E08), 17+ (E09), 17+ (E10), 17+ (E11), 17+ (E12), 17+ (E13), 17+ (E14), 17+ (E15), 17+ (E16), 17+ (E17), 17+ (E18), 17 + (E19), 17+ (E20), 17+ (E21) , “17+ (F01)”, “17+ (F02)”, “17+ (F03)”, “17+ (F04)”, “17+ (F05)”.
18+ (A01), 18+ (A02), 18+ (A03), 18+ (A04), 18+ (A05), 18+ (A06), 18 + (A07), 18+ (A08), 18+ (A09), 18+ (B01), 18+ (B02), 18+ (B03), 18+ ( B04), 18+ (B05), 18+ (B06), 18+ (C01), 18+ (C02), 18+ (C03), 18+ (C04) , 18+ (C05), 18+ (C06), 18+ (C07), 18+ (C08), 18+ (C09), 18+ (C10), 18+ (C11), 18+ (C12), 18+ (C13), 18+ (C14), 18+ (C15), 18+ (D01), 18 + (D02), 18+ (D03), 18+ (D04), 18+ (D05), 18+ (D06), 18+ (D07), 18+ ( D08), 18+ (E01), 18+ (E02), 18+ (E03), 18+ (E04), 18+ (E05), 18+ (E06) , 18+ (E07), 18+ (E08), 18+ (E09), 18+ (E10), 18+ (E11), 18+ (E12), 18+ (E13), 18+ (E14), 18+ (E15), 18+ (E16), 18+ (E17), 18+ (E18), 18 + (E19), 18+ (E20), 18+ (E21) , “18+ (F01)”, “18+ (F02)”, “18+ (F03)”, “18+ (F04)”, “18+ (F05)”.
19+ (A01), 19+ (A02), 19+ (A03), 19+ (A04), 19+ (A05), 19+ (A06), 19 + (A07), 19+ (A08), 19+ (A09), 19+ (B01), 19+ (B02), 19+ (B03), 19+ ( B04), 19+ (B05), 19+ (B06), 19+ (C01), 19+ (C02), 19+ (C03), 19+ (C04) , 19+ (C05), 19+ (C06), 19+ (C07), 19+ (C08), 19+ (C09), 19+ (C10), 19+ (C11), 19+ (C12), 19+ (C13), 19+ (C14), 19+ (C15), 19+ (D01), 19 + (D02), 19+ (D03), 19+ (D04), 19+ (D05), 19+ (D06), 19+ (D07), 19+ ( D08), 19+ (E01), 19+ (E02), 19+ (E03), 19+ (E04), 19+ (E05), 19+ (E06) , 19+ (E07), 19+ (E08), 19+ (E09), 19+ (E10), 19+ (E11), 19+ (E12), 19+ (E13), 19+ (E14), 19+ (E15), 19+ (E16), 19+ (E17), 19+ (E18), 19 + (E19), 19 + (E20), 19 + (E21) , “19+ (F01)”, “19+ (F02)”, “19+ (F03)”, “19+ (F04)”, “19+ (F05)”.
`` 20+ (A01) '', `` 20+ (A02) '', `` 20+ (A03) '', `` 20+ (A04) '', `` 20+ (A05) '', `` 20+ (A06) '', `` 20 + (A07), 20+ (A08), 20+ (A09), 20+ (B01), 20+ (B02), 20+ (B03), 20+ ( B04), 20+ (B05), 20+ (B06), 20+ (C01), 20+ (C02), 20+ (C03), 20+ (C04) ”,“ 20+ (C05) ”,“ 20+ (C06) ”,“ 20+ (C07) ”,“ 20+ (C08) ”,“ 20+ (C09) ”,“ 20+ (C10) ”, `` 20+ (C11) '', `` 20+ (C12) '', `` 20+ (C13) '', `` 20+ (C14) '', `` 20+ (C15) '', `` 20+ (D01) '', `` 20 + (D02), 20+ (D03), 20+ (D04), 20+ (D05), 20+ (D06), 20+ (D07), 20+ ( D08), 20+ (E01), 20+ (E02), 20+ (E03), 20+ (E04), 20+ (E05), 20+ (E06) , 20+ (E07), 20+ (E08), 20+ (E09), 20+ (E10), 20+ (E11), 20+ (E12), 20+ (E13), 20+ (E14), 20+ (E15), 20+ (E16), 20+ (E17), 20+ (E18), 20 + (E19), 20+ (E20), 20+ (E21) , “20+ (F01)”, “20+ (F02)”, “20+ (F03)”, “20+ (F04)”, “20+ (F05)”.
21+ (A01), 21+ (A02), 21+ (A03), 21+ (A04), 21+ (A05), 21+ (A06), 21 + (A07), 21+ (A08), 21+ (A09), 21+ (B01), 21+ (B02), 21+ (B03), 21+ ( B04), 21+ (B05), 21+ (B06), 21+ (C01), 21+ (C02), 21+ (C03), 21+ (C04) , 21+ (C05), 21+ (C06), 21+ (C07), 21+ (C08), 21+ (C09), 21+ (C10), 21+ (C11), 21+ (C12), 21+ (C13), 21+ (C14), 21+ (C15), 21+ (D01), 21 + (D02), 21+ (D03), 21+ (D04), 21+ (D05), 21+ (D06), 21+ (D07), 21+ ( D08), 21+ (E01), 21+ (E02), 21+ (E03), 21+ (E04), 21+ (E05), 21+ (E06) , 21+ (E07), 21+ (E08), 21+ (E09), 21+ (E10), 21+ (E11), 21+ (E12), 21+ (E13), 21+ (E14), 21+ (E15), 21+ (E16), 21+ (E17), 21+ (E18), 21 + (E19), 21+ (E20), 21+ (E21) , “21+ (F01)”, “21+ (F02)”, “21+ (F03)”, “21+ (F04)”, “21+ (F05)”.
22+ (A01), 22+ (A02), 22+ (A03), 22+ (A04), 22+ (A05), 22+ (A06), 22 + (A07), 22+ (A08), 22+ (A09), 22+ (B01), 22+ (B02), 22+ (B03), 22+ ( B04), 22+ (B05), 22+ (B06), 22+ (C01), 22+ (C02), 22+ (C03), 22+ (C04) , 22+ (C05), 22+ (C06), 22+ (C07), 22+ (C08), 22+ (C09), 22+ (C10), 22+ (C11), 22+ (C12), 22+ (C13), 22+ (C14), 22+ (C15), 22+ (D01), 22 + (D02), 22+ (D03), 22+ (D04), 22+ (D05), 22+ (D06), 22+ (D07), 22+ ( D08), 22+ (E01), 22+ (E02), 22+ (E03), 22+ (E04), 22+ (E05), 22+ (E06) , 22+ (E07), 22+ (E08), 22+ (E09), 22+ (E10), 22+ (E11), 22+ (E12), 22+ (E13), 22+ (E14), 22+ (E15), 22+ (E16), 22+ (E17), 22+ (E18), 22 + (E19), 22+ (E20), 22+ (E21) , “22+ (F01)”, “22+ (F02)”, “22+ (F03)”, “22+ (F04)”, “22+ (F05)”.
`` 23+ (A01) '', `` 23+ (A02) '', `` 23+ (A03) '', `` 23+ (A04) '', `` 23+ (A05) '', `` 23+ (A06) '', `` 23 + (A07), 23+ (A08), 23+ (A09), 23+ (B01), 23+ (B02), 23+ (B03), 23+ ( B04), 23+ (B05), 23+ (B06), 23+ (C01), 23+ (C02), 23+ (C03), 23+ (C04) ”,“ 23+ (C05) ”,“ 23+ (C06) ”,“ 23+ (C07) ”,“ 23+ (C08) ”,“ 23+ (C09) ”,“ 23+ (C10) ”, 23+ (C11), 23+ (C12), 23+ (C13), 23+ (C14), 23+ (C15), 23+ (D01), 23 + (D02), 23+ (D03), 23+ (D04), 23+ (D05), 23+ (D06), 23+ (D07), 23+ ( D08), 23+ (E01), 23+ (E02), 23+ (E03), 23+ (E04), 23+ (E05), 23+ (E06) , 23+ (E07), 23+ (E08), 23+ (E09), 23+ (E10), 23+ (E11), 23+ (E12), 23+ (E13), 23+ (E14), 23+ (E15), 23+ (E16), 23+ (E17), 23+ (E18), 23 + (E19), 23+ (E20), 23+ (E21) , “23+ (F01)”, “23+ (F02)”, “23+ (F03)”, “23+ (F04)”, “23+ (F05)”.
24+ (A01), 24+ (A02), 24+ (A03), 24+ (A04), 24+ (A05), 24+ (A06), 24 + (A07), 24+ (A08), 24+ (A09), 24+ (B01), 24+ (B02), 24+ (B03), 24+ ( B04), 24+ (B05), 24+ (B06), 24+ (C01), 24+ (C02), 24+ (C03), 24+ (C04) , 24+ (C05), 24+ (C06), 24+ (C07), 24+ (C08), 24+ (C09), 24+ (C10), `` 24+ (C11) '', `` 24+ (C12) '', `` 24+ (C13) '', `` 24+ (C14) '', `` 24+ (C15) '', `` 24+ (D01) '', `` 24 + (D02), 24+ (D03), 24+ (D04), 24+ (D05), 24+ (D06), 24+ (D07), 24+ ( D08), 24+ (E01), 24+ (E02), 24+ (E03), 24+ (E04), 24+ (E05), 24+ (E06) , 24+ (E07), 24+ (E08), 24+ (E09), 24+ (E10), 24+ (E11), 24+ (E12), 24+ (E13), 24+ (E14), 24+ (E15), 24+ (E16), 24+ (E17), 24+ (E18), 24 + (E19) '', `` 24+ (E20) '', `` 24+ (E21) '' , “24+ (F01)”, “24+ (F02)”, “24+ (F03)”, “24+ (F04)”, “24+ (F05)”.

Examples of known fungicides, insecticides and acaricides used as the active ingredient B of the present invention include compounds selected from the following groups.
Active ingredient group B-VII (bactericidal agent): sulfur (Sulfur), lime sulfur mixture (Lime sulfur), basic copper sulfate (Copper sulfate), iprobenfos (Iprobenfos), edifenfos (Edifenphos), torukurofofos methyl ( Tolclofos-methyl, Thiram, Polycarbamate, Zineb, Manzeb, Mancozeb, Propineb, Prothiobate, Thiophate, Thiophate Salt (Iminoctadine triacetate), iminoctadine albesylate (Im noctadine albesilate, mepronil (Mepronil), flutelanil (Flutamanyl) , Flusulfamide, chlorothalonil, cresoxime-methyl, phenoxanil, hymexazole, echromezole, flumethazole Luimide (Fluoromide), Procymidone (Vinclozoline), Triadimefon (Triadimefon), Vitertanol (Bittertanol), Triflumizol (Fluconol), Ipconazole (Ipconazole) (Ipconazole) (Difenoconazole), Microbutanil, Tetraconazole, Hexaconazole, Tebuconazole, Thiadinil, Imibenconazole (Imibenconazole) conazole, Prochloraz, Pefurazoate, Cyproconazole, Isoprothiolane, Fenarimol, Pyrimethanil, Pyrimethanil, Pyrimethanil ), Triforine, dichromezin, azoxystrobin, thiadiazine, captan, probenazole, acibenzoral Smethyl (Acibenol) r S-methyl), Fthalide, Tricyclazole, Pyroquilone, Chinomethionate, Oxolinic acid, dithianone, cinemycin, c Polyoxin, Blasticidin, Streptomycin, Fluazinam, Trichlamide, Amisulbrom.

Active ingredient group B-VIII (insecticide, acaricide): Cyenopyrafen, Ethion, Trichlorfonate, Metamidophos, Acephate, Dichlorvos, Dichlorvos Monocrotophos, Malathion, Formothion, Mecarbam, Vamidion, Thiometon, Dithiodemethone, Oxydeprothone, Oxydeprothone Methy Parathion, Fenitrothion (Fentitrothion), Cyanophos (Cyanophos), Propafos (Propafos), Fentione (Fentithios), Profenofos (Profenofos), Isofenphos (Isofenphos), Temephos (Temefos), Temefos (Temefos) Phosphine (Dimethylvinphos), Chlorfevinphos (Chlorfenvinphos), Tetrachlorvinphos (Tetrachlorvinphos), Hoxim (Isoxathion), Pyraclofos (Pyraclofos), Methidathion (Methidathion) on), Chlorpyrifos (Pyridaphenthion), Diazinon (Diazinon), Pirimiphos-methyl (Phosalone), Phosmet (Phosme), Phosmet (Phosme) Mesulfenfos), DPS (NK-0795), Isoamidophos (Isamifofos), Enaprofos (Ethoprofos), Fenthion (Sulprofos), Pyrethrin (Pyrethroid), Allethrin (P) in), Resmethrin (Remethrin), Permethrin, Tefluthrin, Bifenthrin, Fenpropatin, Cypermethrin, alpha cypermethrin, alpha cypermethrin Halothrin (Lambda-cyhalothrin), Deltamethrin (Decamethrin), Acrinathrin, Fenvalerate, Esfenvalerate, Cycloprothrin (Cycloprothrin) enprox, Halfenprox, Silafluofen, Flucitrinate, Fluvalinate, Mesomyl, Thiodicarb, Cartol, Cartol, Cartap Xylylcarb, Propoxur, Fenoxycarb, Fenobcarb, Ethiofencarb, Fenothiocarb, Biphenazyl (Bifenate) Bamate 2-secondary-Butylphenyl-N-methylcarbamate), carbaryl (Caryderm), pirimicarb (Pirimicarb), furothicarb (Furathiocarb), benfurencarb (Benfuracarb), diafenthuron (Difurenturon) Hexaflumuron, Novaluron, Lufenuron, Flufenoxuron, Chlorfluazuron, Fenbutatin oxide Tricyclohexyl tin hydroxide (Sodium oleate), Sodium oleate, Potassium oleate, Metoprene, Hydroprel (B), Binaprachlor (B) Dicofol, Kelsen (Dicofol), Chlorbenzilate, Phenylobromolate, Tetradifon, Bensultap, Benzoximate, Tebufenodif , Methoxyfenozide (methoxyfenozide), pyridalyl (Pyridalyl), metaflumizone (Metaflumizone), flubendiamide (Flubendiamide), chromafenozide (chromafenozide), propargite (Propargite), acequinocyl (Acequinocyl), endosulfan (Endosulfan), diofenolan (Diofenolan), chlorfenapyr (Chlorfenapyr ), Fenpyroximate, Tolfenpyrad, Fipronil, Tebufenpyrad, Triazamate, Etoxa Etoxazole, Hexythiazox, Nicotine sulfate, Nitenpyram, Acetamiprid, Thiaprid, Thiapid dinotefuran, pyriproxyfen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC (tripropyli) Cyanurate Tripropylisocyanurate, Pymetrozine, Clofentezine, Buprofezin, Polyacin (Thiocyclam), Thiocyclam (N), Thiocyclam (N) Milbemectin, Emamectin benzoate, Spinosad, BT (Bacillus thuringiensis), Azadirach (Azadirach) in), rotenone (Rotenone), hydroxypropyl starch (Hydroxypropyl starch), levamisole hydrochloride (Levamisole), tartaric acid morantel (Morantel tartrate), Mona Kurosupo potassium-Fimatopagamu (Monacrosporium phymatophagum).

[Active ingredient A] selected from compound (I) and [Active ingredient B] selected from known nematicides, fungicides, insecticides and acaricides in the composition and method of the present invention A suitable mixing ratio is 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.1 to 10 parts by weight, based on 1 part by weight of the active ingredient A. It is.
In the composition of the present invention and the method of the present invention, the preferred treatment amount of the active ingredient compound depends on the type of target disease to be controlled and the like, but usually the active ingredient A is 0.1 to 1000 ga.i./ha. The active ingredient B is 0.1 to 1000 ga.i./ha, preferably the active ingredient A is 1 to 300 ga.i./ha, and the active ingredient B is 1 to 300 ga.i./ha. .

The composition of the present invention is predicted to generate nematodes in an amount effective for controlling various nematodes in the form as it is to control various nematodes, or diluted or suspended as appropriate with water or the like. The target plant, its seeds, or a cultivation carrier for sowing may be used by applying ordinary methods, for example, rice nursery box application, seed dressing application method, seed disinfection method, planting hole treatment, etc. It can be used in application methods such as stock-source treatment, row treatment, and soil mixing treatment.
In addition, for nematodes that occur in field crops such as fruit trees, cereals and vegetables, seed treatment such as dressing and soaking, soaking treatment of seedling roots, cropping during sowing, cultivation containers and planting holes for raising seedlings After irrigation, foliar application, mixing treatment, etc., to a seedling carrier such as a plant source, watering is performed and the plant is absorbed and used. In hydroponics, you may process to a hydroponic solution.
As a seed treatment method, for example, according to a method known in the technical field, for example, a method of immersing seeds in a liquid state without diluting or diluting a liquid or solid preparation, or a solid preparation or A method in which a liquid preparation is mixed with seeds, dressed, etc., and adhered to the surface of the seeds, a method in which the seeds are mixed with a highly adhesive carrier such as resin or polymer, and a seed is coated in a single layer or multiple layers, planting At the same time, there can be mentioned a method of spraying around the seeds. The term “seed” for performing seed treatment is broadly synonymous with the “reproduction plant body” in the present invention, and in addition to seeds, vegetative propagation such as bulbs, tubers, seeds, bulbs or stems for cuttings cultivation. It contains plant bodies for use.

The soil or plant carrier in carrying out the method of the present invention indicates a support for cultivating a plant, and the material is not particularly limited, but any material that can grow a plant may be used. For example, it contains various soils, seedling mats, water, etc., sand, vermiculite, cotton, paper, diatomaceous earth, agar, gel material, polymer material, rock wool, glass wool, wood chip, bark, pumice, etc. Can also be included.
Examples of application methods to the soil include, for example, a method in which a liquid or solid preparation is not diluted or diluted with water, but is applied to the vicinity of a plant location, a nursery bed for raising seedlings, before sowing or planting a plant. The method of spraying powder, wettable powder, granule wettable powder, granule, etc. before planting holes, crops, etc. can be mentioned.
As an application method to a seedling box for paddy rice, the dosage form may vary depending on the application time, such as sowing application, greening period application, transplantation period application, etc., but powder, granule wettable powder, granule, etc. It may be applied in the dosage form. These can be applied by mixing with the soil, and the soil can be mixed with the powder, granulated wettable powder or granule, for example, mixed with soil, covered soil, mixed into the entire soil, etc. it can. In addition, the soil and various preparations may be applied alternately in layers.

The time of application at the time of sowing may be before sowing, at the same time, after sowing, or after covering.
In field crops such as potatoes, sweet potatoes, soybeans, etc., it is preferable to treat the seeds directly in the vicinity of the plant body from seeding to seedling raising. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on a cultivation carrier in the vicinity of the plant being cultivated is suitable. Examples of the treatment include a spray treatment using a granule, or an irrigation treatment in a liquid of a drug diluted or not diluted with water.
As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid medicine or the granule spraying treatment to the nursery bed for raising the seedling can be performed. Moreover, a granule can also be processed to a planting hole at the time of planting, and can be mixed with the cultivation support | carrier of the transplanting site vicinity.
“Plants” refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, genetically modified crops (herbicide-resistant crops, pest-resistant crops incorporating insecticidal protein production genes, diseases Disease-resistant crops, resistance-enhancing crops, preservability-enhancing crops, yield-enhancing crops, etc. that incorporate resistance-inducing substance production genes), appreciation plants that love their shape and shape, or vascular plants such as parks and streets (Tracheophyta) means. Specific examples include the following plants, but specific examples of plants are not limited to these.

Pinaceae plants belonging to Pinaceae, such as Japanese red pine (Pinus densiflora), European red pine Scots Pine (Pinus sylvestris), Japanese black pine (Pinus thunbergii).
Pepper (Piper nigrum) such as Pepperaceae (Piperaceae), Avocado Avocado (Persea americana) and other magnoliaceae (Lauraceae) etc., magnoliids,
Konjac (Amorphophallus konjac), taro edode (Colocasia esculenta) and other taro (Araceae), Chinese yam (Dioscorea batatas), yam Japanese yam (Dioscorea japonica) and other yam (Dioscoreacesum var) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Leek Welsh onion (Allium fistulosum), Garlic Garlic (Allium sativum), Chives Chives (Allium schoenoprasum), Asatsuchi Chive (Allium schoenofosum var) Japanese leek Oriental garlic (Allium tuberosum), Alliumaceae such as Scallion (Allium x wakegi), Asparagus Asparagus (Asparagus officinalis), etc. (Elaeis guineensis) and other palms (Arecaceae) arecaidea (Arecoideae), na Date palm (Phoenix dactylifera) and other palms (Arecaceae) Talipot subfamily (Coryphoideae), pineapples Pineapple (Ananas comosus) and other pineapples (Bromeliaceae), rice Rice (Poryae sativa) and other poaceae Family (Ehrhartoideae), bentgrass Bent grass (Agrostis spp.), Blue grass (Poa spp.), Barley Barley (Hordeum vulgare), wheat Wheat (Triticum aestivum, T. durum), rye Rye (Secale cereale), etc. Poaceae Strawberry subfamily (Pooideae), Googyushiba Bermuda grass (Cynodon dactylon), Shiba Grass (Zoysia spp.), Etc. Sorgum (Sorghum bicolor), Corn Corn (Zea mays), etc. Gramineae (Poaceae) Millet subfamily (Panicoideae), Banana Banana (Musa spp.), Etc. C family (Musaceae), Zingiber mioga Myoga (Zingiber mioga), ginger Ginger (Zingiber officinale) ginger family (Zingiberaceae) monocots that belong to such as (monocots).
Lotus root (Nelumbo nucifera) and other lotus families (Nelumbonaceae), groundnuts Peanut (Arachis hypogaea), chickpeas (Cicer arietinum), lentil Lentil (Lens culinaris), peas Pea (Pisum sativum), broad bean Bia bea , Soybean Soybean (Glycine max), common bean (Phaseolus vulgaris), adzuki bean (Vigna angularis) adzuki bean (Vigna angularis), legume (Fabaceae) such as cowpea (Vigna unguiculata), Asapaceae (Cannabaceae) such as hop Hop (Humulus lupulus) ), Fig Tree (Ficus carica), Mulberry (Morus spp.), Etc. (Moraceae), Jujube (Ziziphus jujuba), etc. (Rhamnaceae), Strawberry Strawberry (Fragaria), Rose Rose (Rosa) spp.) and other Rosaceae (Rosaceae) subfamily (Rosoideae), loquat Japanese loquat (Eriobotrya japonica), apple Apple (Malus pumila), pear European Pear ( Pyrus communis), pear Nashi Pear (Pyrus pyrifolia var. Culta) and other roses (Rosaceae) pear subfamily (Maloideae), peach Peach (Amygdalus persica), apricot Apricot (Prunus armeniaca), sweet cherry (Prunus avium), prunes Roses such as Prune (Prunus domestica), Almond Almond (Prunus dulcis), Japanese plum Apricot (Prunus mume), Japanese plum Plum (Prunus salicina), Oshima cherry (Cerasus speciosa), Yoshino cherry (Cerasus x yedoensis'Somei-yoshino ') (Rosaceae) Cherry subfamily (Prunoideae), Tougan Winter melon (Benincasa hispida), Watermelon Watermelon (Citrullus lanatus), Yugao Bottle gourd (Lagenaria siceraria var. Hispida), Loofah Luffa (Luffa cylindrica), Pumpkin Pumpkin (Pumpkin) , Zucchini (Cucurbita pepo), Bitter melon (Momordica charantia var. Pavel), Melon Muskmelon (Cucumis melo), Oriental pickli ng melon (Cucumis melo var. conomon), cucumber Oriental melon (Cucumis melo var. makuwa), cucumber Cucumber (Cucumis sativus) and other Cucurbitaceae, chestnut Japanese Chestnut (Castanea crenata) and other beech (Fagaceae), Walnut Walnut (Juglans spp.) And other walnuts (Juglandaceae), cashew nut Cashew (Anacardium occidentale), mango Mango (Mangifera indica), pistachio Pistachio (Pistacia vera), etc. ) Etc. (Rutaceae) Henruda subfamily (Rutoideae), Daidai Bitter orange (Citrus aurantium), Lime Lime (Citrus aurantifolia), Hassaku Hassaku orange (Citrus hassaku), Yuzu Yuzu (Citrus junos), Lemon Lemon (Citrus limon) ), Natsumikan (Citrus natsudaidai), Grapefruit (Citrus x paradisi), Orange Orange (Citrus sinensis) Kabosu (Citrus sphaerocarpa), Sudachi (Citrus sudachi), Ponkan Mandarin Orange (Citrus tangerina), Satsuma (Citrus unshiu), Kumquat Kumquat (Fortunella spp.), Etc. (Rutaceae) Horseradish (Armoracia rusticana), Mustard (Brassica juncea), Takana Takana (Brassica juncea var. Integrifolia), Brassica rapeseed (Brassica napus), Cauliflower (Brassica oleracea rac. Var. Botrytis var. Botrytis var. capitata), brussels sprout (Brassica oleracea var. gemmifera), broccoli Broccoli (Brassica oleracea var. italica), green pak choi (Brassica rapa var. chinensis), Nozawana (Brassica rapa var. hakabura) (Brassica rapa var. Nippo-oleifera), Mizuna Potherb Mustard (Brass ica rapa var. nipposinica), Chinese cabbage Napa cabbage (Brassica rapa var. pekinensis), Komatsuna Turnip leaf (Brassica rapa var. Raphanus sativus var. Longipinnatus), Wasabi (Wasabia japonica) and other Brassicaceae (Brassicaceae); , Cacao (Theobroma cacao) such as Malvaceae, Grapes Grape (Vitis spp.) Grapes (Vitaceae), sugar beet Sugar beet (Beta vulgaris ssp. Vulgaris var. Altissima), table beet Table beet (Beta vulgaris ssp. vulgaris var. vulgaris), Amaranthaceae such as spinach Spinach (Spinacia oleracea), Polygonaceae such as buckwheat Buckweat (Fagopyrum esculentum) Persimmon (Diospyros kaki) and other oysters (Ebenaceae), Cha Tea plant (Camellia sinensis) and other camellia (Theaceae), Kiwifruit Kiwifruit (Actinidia deliciosa and A. chinensis) Blueberry (Vaccinium spp.), Cranberry (Vaccinium spp.) And other azaleas (Ericaceae), Coffee tree Coffee plants (Coffea spp.) And other Rubiaceae, lemon balm Lemon balm (Melissa officinalis), mint Mint (Mentha spp.), basil Basil (Ocimum basilicum), perilla Shiso (Perilla frutescens var. crispa), egoma (Perilla frutescens var. frutescens), sage Common Sage (Salvia officinalis), thyme Thyme (Thymus spp.) Lamiaceae), Sesame (Pedaliaceae) such as Sesame (Sesamum indicum), Oleaceae such as Olive Olive (Olea europaea), Sweet potato (Ipomo) ea batatas), Convolvulaceae, Tomato (Solanum lycopersicum), Eggplant Eggplant (Solanum melongena), Potato Potato (Solanum tuberosum), Pepper Chili pepper (Capsicum annuum), Bell pepper (Capsicum annusum var. '), Solanaceae (Solanaceae) such as tobacco Tobacco (Nicotiana tabacum), celery Celery (Apium graveolens var. Dulce), coriander Coriander (Coriandrum sativum), Japanese honeywort (Cryptotaenia Canadensis subsp. Japonica), carrot carrot (Daucus carrot (Daucus subsp. sativus), parsley Parsley (Petroselium crispum), Italian parsley Italian parsley (Petroselinum neapolitanum), etc. (Apiaceae), Udo Udo (Aralia cordata), araki (Aralia elata), etc. Araliaceich, artichoke (Cynara scolymus) and other asteraceae (Asteraceae) thistle subfamily (Carduoideae), chrysanthemum Chicory (C ichorium intybus), lettuce Lettuce (Lactuca sativa), etc. Authentic dicots (eudicots) belonging to Asteraceae and Asteraceae, such as (Petasites japonicus) and Burdock (Arctium lappa).

“Nematode” means a nematode that causes pathological damage to plants, and specifically includes the following nematodes, but specific examples of nematodes are not limited to these. Absent.
For example, sweet potato root nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javamica), arenaria root-knot nematode (Meloidogyne yne) (Meloidogyne usneum) ) And other apherenchoides (Aphelenchoididae), Paratylenchus (Paratylenchus sp) and other paratylenids (Patylenchus coffeae), sawtooth nematode (Pratylenchus crenatus) Pratylenchus gotohi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus vulnus, Sorghum Pratylencidae (Pratylenchus zeae) and other species (Pratylenchidae), clover cyst nematode (Heterodera trifolii), wheat cyst nematode (Heterodera avenae), okabo cyst nematode (Heterodera elachista), soybean cyst nematode (Heterodera glycines) Nematode (Globodera rostochiensis), Potato white cyst nematode (Globodera pallida), Heterodera nematode (Heterodera schachtii), etc. Radopholus similis), Nemoglyso nematodes, such as Radopholus citrophilus.
Longidoridae (Longidorus martini), Longirus martini, Longirus sp. , Trichodorsaceae such as Paramitrichodorus minor, Paratyrichodorus porosus, Tylenchulus semipenetrans, etc., and Sellamanaceae such as Sphaeronema camelliae ), Kayasayawa nematode (Hemicriconemoides brachyurus), Kanaya Sayawa nematode (Hemicriconemoides kanayaensis), citrus nematode (Ogma civellae), Ogma coffeae, Ogma coffeae, Ogma dryum Ogma serratum and other chestnut nematodes (Paratylenchus curvitatus), Paratylenchus (Paratylenchus elachistus) and other apherenaceae such as Aphelenchus avenae Aferenchoides family such as nematode (Aphelenchoides besseyi), strawberry nematode (Aphelenchoides fragariae), lily nematode (Aphelenchoides lilium), abalone nematode (Aphelenchoides ritzemabosi), and pine wood nematode (Bursaphelenchus xylophilus).

Furthermore, the composition of the present invention is also effective for animal parasitic nematodes such as roundworms, gourds, anisakis, filariae, bancroft filamentous insects, rotiferous filamentous insects, and helminths.
In addition, the composition of the present invention prevents many nematodes that occur in vascular plants (Tracheophyta) such as pine (Pinales), magnolias, monocots, monocots and eudicots. Can be effectively controlled.
The nematodes are Nematoda, Tylenchida, Rhabditida, Dorylaimida, Monhysterida, Araeolaimida, Chromadorida, and Enoprus. Examples include Enoplida, Mononchida, and Dorylaimida. Among these, the composition of the present invention is a phytopathogenic nematode belonging to the order of the genus Coleoptera, Coleoptera, Nisehari nematode, and Dorylaimida. Exhibits excellent control effects at low concentrations against varieties.

In the composition of the present invention, an active ingredient A selected from the compound (I) and an active ingredient B selected from known nematicides, fungicides, insecticides and acaricides are mixed and used as a mixture. You can also. Usually mixed with a suitable solid carrier or liquid carrier, and if desired, surfactant, penetrant, spreading agent, thickener, antifreeze agent, binder, anti-caking agent, disintegrant, antifoaming Additives, preservatives, anti-decomposition agents, etc., add soluble concentrate, emulsion (emulsifiable concentrate), wettable powder, water-soluble solvent, water dispersible granule ), Water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule ), Tablets, and emulsifiable gels, etc., and preferably used for practical use.
Further, from the viewpoint of labor saving and safety improvement, the preparations of the above arbitrary dosage forms can be encapsulated and provided as water-soluble packaging bodies such as water-soluble capsules and water-soluble film bags.

Examples of the solid support include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, dikelite, Natural minerals such as allophane, shirasu, giraffe, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, diatomaceous earth, etc .; Quality baked goods; inorganic salts such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium chloride; glucose, fructose, sucrose , Sugars such as lactose; starch Polysaccharides such as powdered cellulose and dextrin; Organic substances such as urea, urea derivatives, benzoic acid, benzoic acid salts; plants such as wood flour, cork flour, corn cobs, walnut shells, tobacco stems; fly ash, white carbon (For example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.), fertilizers and the like.

Examples of liquid carriers include aromatic hydrocarbons such as xylene, alkyl (C ₉ or C ₁₀ etc.) benzene, phenyl xylyl ethane, alkyl (C ₁ or C ₃ etc.) naphthalene; machine oil, normal paraffin, isoparaffin Aliphatic hydrocarbons such as naphthene, aromatic hydrocarbons such as kerosene, and aliphatic hydrocarbons; alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol, and benzyl alcohol; ethylene glycol, propylene glycol, diethylene glycol, hexylene Polyhydric alcohols such as glycol, polyethylene glycol and polypropylene glycol; propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol Ethers such as no ethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether; ketones such as acetophenone, cyclohexanone and γ-butyrolactone; fatty acid methyl esters, succinic acid dialkyl esters, glutamic acid dialkyl esters, adipic acid Esters such as dialkyl esters and dialkyl phthalates; Acid amides such as N-alkyl (C ₁ , C ₈ or C ₁₂ ) pyrrolidone; Fats and oils such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, castor oil Dimethyl sulfoxide, water and the like.
These solid carriers and liquid carriers may be used alone or in combination of two or more.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Oxyethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, Nonionic surfactants such as alkyl glycosides; alkyl sulfate salts, alkylbenzene sulfonates, lignin sulfonates, alkyls Succinate, naphthalenesulfonate, alkylnaphthalenesulfonate, salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxyethylene (Mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg, polyacrylate, polymaleate and maleate) Copolymer of acid and olefin), anionic surfactant such as polystyrene sulfonate; cationic surfactant such as alkylamine salt and alkyl quaternary ammonium salt; amphoteric surfactant such as amino acid type and betaine type Agent; System surfactant, fluorine-based surfactants, and the like.
The content of these surfactants is not particularly limited, but is preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the composition of the present invention, preferably 0.1 to 15 parts by weight. Part is more desirable. These surfactants may be used alone or in combination of two or more.

The application amount of the composition of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but in general, the amount of active ingredient is about 0.005 to 50 kg per hectare (ha). Is suitably 0.01 to 2 kg.
Next, formulation examples of preparations when using the composition of the present invention are shown. However, the formulation examples of the present invention are not limited to these.
In the following formulation examples, “parts” means parts by weight, and “active ingredient compound” means active ingredient A selected from compound (I) or compound (I), a known nematicide, bactericidal agent It is a general term for an active ingredient B selected from agents, insecticides and acaricides.

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

〔emulsion〕
Active ingredient compound 0.1 to 30 parts Organic solvent 45 to 95 parts Surfactant 4.9 to 30 parts Water 0 to 50 parts Others 0 to 10 parts Others include, for example, spreading agents, decomposition inhibitors, etc. .

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

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

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

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

[Dust]
Active ingredient compound 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, drift inhibitors and decomposition inhibitors.

Next, although the formulation example which uses this invention composition as an active ingredient is shown more concretely, this invention is not limited to these.
In the following formulation examples, “parts” means parts by weight.

[Formulation 1] wettable powder
Compound No. 10 10 parts Compound No. A08 10 parts Pyrophyllite 74 parts Solpol 5039 4 parts (trade name, mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd.)
Carplex # 80D 2 parts (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co.)
The above is uniformly mixed and ground to obtain a wettable powder.

[Formulation Example 2] Emulsifiable concentrate
Compound No. 23 3-part compound no. C07 2 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 15 parts (trade name, mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Co., Ltd.)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 3] Emulsifiable concentrate
Compound No. 15 2-part compound no. C01 2 parts DBE 36 parts (trade name, dimethyl adipate, dimethyl glutarate, dimethyl succinate mixture: manufactured by INVISTA)
Isobutyl adipate 30 parts N-methylpyrrolidone 10 parts Soprophor BSU 14 parts (trade name, nonionic surfactant: manufactured by Rhodia)
6 parts of rhodacal 70BC (trade name, anionic surfactant: manufactured by Rhodia)
The above is uniformly mixed to obtain an emulsion.

[Formulation Example 4] Emulsifiable concentrate
Compound No. 4 2-part compound no. B05 2 parts DBE 11 parts (trade name, dimethyl adipate, dimethyl glutarate, dimethyl succinate mixture: manufactured by INVISTA)
Isobutyl adipate 30 parts N-methylpyrrolidone 5 parts Soprofol BSU 14 parts (trade name, nonionic surfactant: manufactured by Rhodia)
6 parts of rhodacal 70BC (trade name, anionic surfactant: manufactured by Rhodia)
Propylene glycol 10 parts Water 20 parts or more are mixed uniformly to make an emulsion.

[Formulation 5] Suspension concentrate
Compound No. 9 15 parts Compound No. 9 A01 10 parts Agrisol S-710 10 parts (trade name, nonionic surfactant: manufactured by Kao Corporation)
Lnox 1000C 0.5 part (trade name, anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd.)
Xanthan gum 0.2 parts Water 64.3 parts The above is uniformly mixed and then wet-pulverized to form a suspension.

[Composition Example 6] Granule wettable powder (water dispersible granule)
Compound No. 9 40 parts Compound No. 9 C01 35 parts Hightenol NE-15 5 parts (trade name, anionic surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (trade name, anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd.)
Carplex # 80D 10 parts (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co.)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.

[Formulation Example 7] Granule
Compound No. 10 3 parts Compound No. E20 2 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to form granules.

[Formulation Example 8] dustable powder
Compound No. 5 2 parts Compound No. 5 C07 1 part Carplex # 80D 0.5 part (trade name, synthetic hydrous silicic acid: manufactured by Shionogi & Co.)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts or more is mixed and ground uniformly to form a powder.
In use, each of the above preparations is diluted 1 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare (ha), preferably 0.01 to 10 kg. .

In addition, one or more compounds selected from active ingredient A and one or more compounds selected from active ingredient BI group to B-VIII group of active ingredient B contain both as active ingredients. Can be formulated and used as described above, but drugs containing each compound as an active ingredient can be used separately or applied separately in close proximity to each other in time Is also possible.
In addition, when applied separately in close proximity in time, it is desirable to perform the next spraying after the sprayed drug is sufficiently dried, depending on the control method, the target disease to be controlled, and the like.
In addition, when applied separately, the preferred [active ingredient A] selected from oxime-substituted amide compounds represented by formula (I) and [active ingredient B] selected from known bactericidal or bactericidal active compounds The active ingredient is used in an amount of 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.1 to 100 parts by weight, based on 1 part by weight of [active ingredient A]. 10 parts by weight.

[Synthesis example]
Specific examples of the synthesis of the oxime-substituted amide compound represented by the formula (I) as the active ingredient A of the present invention are shown below, but the synthesis method is not limited to these examples.
The chemical shift value of proton nuclear magnetic resonance ( ¹ HNMR) used for the identification of the compound is 300 MHz (model: JNM-ECX300, manufactured by JEOL Ltd.) using Me ₄ Si (tetramethylsilane) as a reference substance. Measured with
Symbols in proton nuclear magnetic resonance chemical shift values have the following meanings.
s: singlet, d: doublet, t: triplet, q: quartet, m: multiplet, br: broad Note that the name of the solvent used for NMR measurement is shown in parentheses in the chemical shift value data.

Synthesis example 1
(Z) -N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (trifluoromethyl) nicotinamide (compound No.22).
Step 1: Preparation of N- [2- (3,5-dichloropyridin-2-yl) -2-oxoethyl] carbamic acid-tert-butyl 2-bromo-3,5-dichloropyridine 35.1 g in tetrahydrofuran 10 ml solution Then, 116.3 ml of a 1.3 M tetrahydrofuran solution of isopropylmagnesium chloride-lithium chloride complex was added dropwise with stirring at −20 ° C. After completion of dropping, the reaction mixture was stirred at the same temperature for 15 minutes. After completion of the stirring, a solution of N-methoxy-N-methyl-2- (tert-butoxycarbonylamino) acetamide (15.0 g) in tetrahydrofuran (114 ml) was added dropwise to the reaction mixture. After completion of the dropwise addition, the reaction mixture was continuously stirred at the same temperature for 2 hours. After completion of the reaction, 100 ml of a saturated aqueous ammonium chloride solution and 100 ml of water were added to the reaction mixture, followed by extraction with ethyl acetate (200 ml × 2). The obtained organic layers were combined, washed with water (100 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane [gradient of 0:10 to 3: 7 (volume ratio, the same shall apply hereinafter)] to obtain 12.5 g of the desired product. Obtained as pale yellow crystals.
Melting point: 82.0-84.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.51 (d, J = 2.1 Hz, 1H), 7.85 (d, J = 2.1 Hz, 1H), 5.31 (bs, 1H), 4.76 (bs, 2H), 1.47 (s, 9H).

Step 2: Preparation of N- [2- (3,5-dichloropyridin-2-yl) -2- (hydroxyimino) ethyl] carbamic acid-tert-butyl N- [2- (3,5-dichloropyridine- 6.1 g of pyridine was added to a solution of 10.6 g of 2-yl) -2-oxoethyl] carbamic acid-tert-butyl and 4.8 g of hydroxylamine hydrochloride in 87 ml of ethanol. After the addition was complete, the reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. To the obtained residue, 50 ml of water was added and extracted with ethyl acetate (100 ml × 2). The obtained organic layers were combined, dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient 5:95 to 40:60) to obtain 10.1 g of the desired product as a pale yellow resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.52 and 8.47 (d, J = 2.4Hz, 1H), 7.82 and 7.79 (d, J = 2.4Hz, 1H), 5.65 and 5.16 (bs, 1H ), 4.46 and 4.24 (d, J = 5.4Hz, 2H), 1.39 and 1.34 (s, 9H).

Step 3; Preparation of N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] carbamic acid-tert-butyl N- [2- To a solution of 5.0 g of (3,5-dichloropyridin-2-yl) -2- (hydroxyimino) ethyl] carbamic acid-tert-butyl in 16.0 ml of N, N-dimethylformamide, 4.3 g of potassium carbonate and trifluoro 5.4 g of 2,2,2-trifluoroethyl lomethanesulfonic acid was added. After the addition was complete, the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, 100 ml of water was added to the reaction mixture and extracted with ethyl acetate (100 ml × 2). The obtained organic layers were combined, washed with water (50 ml × 2), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient from 0:10 to 3: 7) to obtain 4.8 g of the desired product as a pale yellow oil.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.51 and 8.49 (d, J = 1.8Hz, 1H), 7.80 and 7.78 (d, J = 1.8Hz, 1H), 4.94 (bs, 1H), 4.0-4.65 (m, 4H), 1.39 and 1.34 (s, 9H).

Step 4: Preparation of 2-amino-1- (3,5-dichloropyridin-2-yl) ethanone-O- (2,2,2-trifluoroethyl) oxime hydrochloride N- [2- (3,5 -Dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] carbamic acid-tert-butyl (4.9 g) in 1,4-dioxane (5 ml) was charged with hydrogen chloride (1,4). -25 ml of dioxane solution (4 mol / L) was added. After the addition was complete, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was washed with 20 ml of hexane to obtain 3.1 g of the objective product as light brown crystals.
Melting point: 141.0-143.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.98 (bs, 3H), 8.56 and 8.52 (d, J = 2.1 Hz, 1H), 7.83 and 7.80 (d, J = 2.1 Hz, 1H), 4.72 and 4.54 (q, J = 8.7Hz, 2H), 4.28 and 4.10 (bs, 2H).

Step 5: Preparation of N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (trifluoromethyl) nicotinamide 2 -Amino-1- (3,5-dichloropyridin-2-yl) ethanone-O- (2,2,2-trifluoroethyl) oxime hydrochloride 118 mg in water 0.7 ml in water at room temperature with stirring A solution of 121 mg 2- (trifluoromethyl) nicotinoyl chloride in 0.7 ml dichloromethane and 145 mg potassium carbonate was added. After completion of the addition, the reaction mixture was stirred at the same temperature for 2 hours. After completion of the reaction, an organic layer was separated from the reaction mixture. The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient 5:95 to 50:50) to obtain 141 mg of the desired product as a pale yellow resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.7-8.8 (m, 1H), 8.52 and 8.47 (d, J = 2.1 Hz, 1H), 7.75-7.95 (m, 2H), 7.5-7.65 (m, 1H), 6.51 (bs, 1H), 4.35-4.85 (m, 4H).

Step 6; (Z) -N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (trifluoromethyl) nicotine Preparation of Amide 141 mg of N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (trifluoromethyl) nicotinamide Dissolve in 3.0 ml and use a 100 W high pressure mercury lamp (USHIO, lamp UM-102, lighting device UM-103B-B) in a quartz cell (Fine, fully transparent cell for spectroscopic analysis). For 48 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was washed with 20 ml of hexane to obtain 122 mg of the desired product as pale yellow crystals.
Melting point 118.0-120.0 ° C
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.75-8.8 (m, 1H), 8.52 (d, J = 2.1 Hz, 1H), 7.85-7.95 (m, 1H), 7.83 (d, J = 2.1Hz, 1H), 7.55-7.65 (m, 1H), 6.52 (bs, 1H), 4.58 (d, J = 5.1Hz, 2H), 4.43 (q, J = 8.4Hz, 2H).

Synthesis example 2
(Z) -N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2- (ethoxyimino) ethyl] -2- (difluoromethyl) nicotinamide (Compound No. 23 ).
Step 1: Preparation of 3-chloro-5- (cyclopropylethynyl) pyridine-2-carbonitrile Triethylamine 50. in a solution of 17.37 g 3,5-dichloropyridine-2-carbonitrile in 200 ml N, N-dimethylformamide. 60 g, 7.90 g of cyclopropylacetylene, 2.20 g of copper (I) iodide and 2.10 g of dichlorobis (triphenylphosphine) palladium (II) were added. After the addition was complete, the reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. After completion of the reaction, 500 ml of water was added to the reaction mixture and extracted with ethyl acetate (250 ml × 2). The obtained organic layers were combined, washed with water (500 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 18.40 g of the objective product as a brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.50 (d, J = 1.7Hz, 1H), 7.77 (d, J = 1.7Hz, 1H), 1.45-1.55 (m, 1H), 0.8- 1.05 (m, 4H).

Step 2; Preparation of 1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] ethanone 3-chloro-5- (cyclopropylethynyl) pyridine-2-carbonitrile 9.0 g in tetrahydrofuran 90 ml solution Then, 22 ml of a 3M diethyl ether solution of methylmagnesium bromide was added dropwise with stirring on ice. After completion of the dropwise addition, the reaction mixture was stirred at the same temperature for 40 minutes. After completion of the reaction, the reaction mixture was added dropwise to 200 ml of 1M aqueous hydrochloric acid solution and extracted with ethyl acetate (125 ml × 2). The obtained organic layers were combined, washed with water (100 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 9.6 g of the desired product as a brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.45 (d, J = 1.7 Hz, 1H), 7.72 (d, J = 1.7 Hz, 1H), 2.67 (s, 3H), 1.4-1.6 ( m, 1H), 0.8-1.05 (m, 4H).

Step 3; Preparation of 2-bromo-1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] ethanone 1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] To a solution of 9.6 g of ethanone in 145 ml of tetrahydrofuran was added 16.3 g of trimethylphenylammonium tribromide. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solid precipitated in the reaction mixture was removed by filtration through celite, and the resulting solid was washed with 100 ml of ethyl acetate. The filtrate and ethyl acetate solution were combined and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1: 9) to obtain 12.0 g of the desired product as a light brown solid.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.46 (d, J = 1.7Hz, 1H), 7.76 (d, J = 1.7Hz, 1H), 4.71 (s, 2H), 1.4-1.6 ( m, 1H), 0.8-1.05 (m, 4H).

Step 4; Preparation of 2-bromo-1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] ethanone-O-ethyloxime 2-bromo-1- [3-chloro-5- (cyclo To a solution of 1.5 g of propylethynyl) pyridin-2-yl] ethanone in 20 ml of ethanol was added 885 mg of ethoxyamine hydrochloride. After the addition was complete, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. To the obtained residue, 40 ml of water was added and extracted with ethyl acetate (25 ml × 2). The obtained organic layers were combined, washed with water (30 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient 5:95 to 20:80), and 900 mg of the desired product was converted into a brown resinous substance (E / Z = 3 / Obtained as 2).
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.48 and 8.47 (d, J = 1.7Hz, 1H), 7.74 and 7.73 (d, J = 1.7Hz, 1H), 4.70 and 4.53 (s, 2H ), 4.36 and 4.34 (q, J = 7.2Hz, 2H), 1.4-1.55 (m, 1H), 1.38 and 1.37 (t, J = 7.2Hz, 3H), 0.8-1.0 (m, 4H).

Step 5: Preparation of N- [2- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2- (ethoxyimino) ethyl] phthalimide 2-bromo-1- [3-chloro-5 To a solution of 900 mg of (cyclopropylethynyl) pyridin-2-yl] ethanone-O-ethyloxime in 10 ml of N, N-dimethylformamide was added 656 mg of potassium phthalimide. After the addition was complete, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, 100 ml of water was added to the reaction mixture and extracted with ethyl acetate (50 ml × 3). The obtained organic layers were combined, washed with water (50 ml × 1), dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (gradient 5: 95-30: 70) to obtain 940 mg of the desired product as a yellow resinous substance (E-isomer). It was.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.27 (d, J = 1.8 Hz, 1H), 7.6-7.8 (m, 5H), 4.99 (s, 2H), 4.27 (q, J = 7.0 Hz, 2H), 1.35-1.5 (m, 1H), 1.29 (t, J = 7.0Hz, 3H), 0.7-0.95 (m, 4H).

Step 6; Preparation of 2-amino-1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] ethanone-O-ethyloxime N- [2- [3-Chloro-5- (cyclopropyl) To a solution of ethynyl) pyridin-2-yl] -2- (isopropoxyimino) ethyl] phthalimide in 940 mg in ethanol was added 345 mg of hydrazine monohydrate. After completion of the addition, the reaction mixture was stirred for 3 hours under heating to reflux. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and then the solvent was distilled off under reduced pressure. To the obtained residue, 50 ml of water was added and extracted with ethyl acetate (20 ml × 2). The obtained organic layers were combined and washed with water (30 ml × 2), then dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 610 mg of the crude target product was converted to yellow. Obtained as an oil (E / Z = 1/1). This was directly used in the next step without further purification.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ 8.47 and 8.46 (d, J = 1.7Hz, 1H), 7.71 and 7.67 (d, J = 1.7Hz, 1H), 4.28 and 4.27 (q, J = 7.0Hz, 2H), 3.89 and 3.75 (s, 2H), 1.59 (bs, 2H), 1.4-1.55 (m, 1H), 1.35 and 1.33 (t, J = 7.0Hz, 3H), 0.75-1.0 ( m, 4H).

Step 7; Preparation of N- [2- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2- (ethoxyimino) ethyl] -2- (difluoromethyl) nicotinamide 2- (difluoro To a solution of 66 mg of methyl) nicotinic acid in 2 ml of dichloromethane was added 10 mg of N, N-dimethylformamide and 67 mg of oxalyl chloride. After the addition was complete, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 2 ml of dichloromethane, and 100 mg of 2-amino-1- [3-chloro-5- (cyclopropylethynyl) pyridin-2-yl] ethanone-O-ethyloxime, It was added dropwise to a solution of potassium 150 mg in 2 ml dichloromethane and 2 ml water. After completion of the dropwise addition, the reaction mixture was continuously stirred at room temperature for 2 hours. After completion of the reaction, 5 ml of dichloromethane was added to the reaction mixture, and the organic layer was separated. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 7 to 5: 5 gradient), and 122 mg of the desired product was obtained as a pale yellow resinous substance (E / Z = 3 / 1).
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.77 and 8.72 (dd, J = 4.8, 1.0 Hz, 1H), 8.48 and 8.43 (d, J = 1.7 Hz, 1H), 7.94 and 7.80 (dd , J = 7.8, 1.0Hz, 1H), 7.74 and 7.72 (d, J = 1.7Hz, 1H), 7.48 and 7.44 (dd, J = 7.8, 4.8Hz, 1H), 7.03 and 6.90 (t, J = 54.3 Hz, 1H), 6.90 (bs, 1H), 4.77 and 4.53 (d, J = 5.1Hz, 2H), 4.33 and 4.15 (q, J = 7.0Hz, 2H), 1.4-1.55 (m, 1H), 1.37 and 1.22 (t, J = 7.0Hz, 3H), 0.8-1.0 (m, 4H).

Step 8: Preparation of (Z) -N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2- (ethoxyimino) ethyl] -2- (difluoromethyl) nicotinamide N- [2- [3-Chloro-5- (cyclopropylethynyl) pyridin-2-yl] -2- (ethoxyimino) ethyl] -2- (difluoromethyl) nicotinamide (E / Z = 3/1) Dissolve 122mg in 3ml of ethyl acetate and use a 100W high-pressure mercury lamp (USHIO, lamp UM-102, lighting device UM-103B-B) in a quartz cell (Fine, fully transparent cell for spectroscopic analysis). For 24 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 7 to 5: 5 gradient) to obtain 70 mg of the desired product as a pale yellow resinous substance.
¹ H NMR (CDCl ₃ , Me ₄ Si, 300 MHz) δ8.77 (dd, J = 4.8, 1.0 Hz, 1H), 8.48 (d, J = 1.7 Hz, 1H), 7.94 (dd, J = 7.8, 1.0 Hz, 1H), 7.72 (d, J = 1.7Hz, 1H), 7.48 (dd, J = 7.8, 4.8Hz, 1H), 7.03 (t, J = 54.3Hz, 1H), 6.90 (bs, 1H), 4.53 (d, J = 5.1Hz, 2H), 4.15 (q, J = 7.0Hz, 2H), 1.4-1.55 (m, 1H), 1.22 (t, J = 7.0Hz, 3H), 0.8-1.0 (m , 4H).

Specific examples of the compound (I) that can be produced in the same manner as the synthesis examples described in Synthesis Example 1, Synthesis Example 2 or International Patent Publication (WO2014 / 010737) are shown in Table 2. Compound (I) used in the composition is not limited to these.
The description of “* 1” in the melting point column means that the property of the compound was oily or resinous.

[Table 8]

Wherein the substituents ^{G 1,} respectively, ^{G 1} -1a ~ ^{G 1} -1g ^{below, G 1 -2a, G 1 -2b} , G 1 -3a ~ G 1 -3c, G 1 -7a or ^{G 1} Represents -11a.

Of the compound (I) described in Table 8, Table 9 shows the spectral data of compounds having no melting point in the table.

Next, in order to clarify the usefulness of the present invention, it will be specifically described in the following test examples, but the present invention is not limited thereto.
[Test Example 1] Nematocidal test against sweet potato nematode The following compounds listed in Table 2 and the following compounds listed in Tables 6 and 8 are brought to predetermined concentrations using dimethyl sulfoxide. Similarly, a chemical solution of the test compound was prepared. In addition, 60 μl of 1 wt% potato dextrose agar medium was dispensed into a 96-well plate, and then 30 μl of sterilized water containing sweet potato nematode eggs was added. The number of eggs was 100 per well. Next, from above, 10 μl of the previously prepared test compound solution was added so that the total amount of the drug solution was 100 μl. Then, it left still at 25 degreeC and dark conditions, and the unhatched egg and the inactive larva two days after the chemical | medical agent addition were determined.

According to the following formula 1, efficiency (%) with respect to the untreated section was calculated.
efficacy (%) = (number of inactive larvae in treated area / number of active larvae in non-treated area) x 100 ... (1)
The results of mixing with fosthiazate are shown in Tables 10 and 11, and the results of mixing with abamectin are shown in Tables 12 and 13.
Further, the synergistic effect was calculated from the control value for each chemical concentration using the Colby method (Colby SR 1976, Weeds 15, 20-22). The calculation method is as follows.
E = X + Y-XY / 100
X: Control value of agent A at x concentration Y: Control value of agent B at y concentration E: Theoretical value expected during mixing treatment of agent A and agent B In the results obtained, the observed value is larger than the expected value If the expected value is greater than the observed value, it can be analyzed as an antagonistic effect, and if the observed value is the same as the expected value, it can be analyzed as an additive effect.

[Table 10]
―――――――――――――――
Compound No. Concentration (ppm) Control Value ―――――――――――――――
15 0.1 30
9 0.1 20
4 0.1 0
20 0.1 10
23 0.1 50
10 0.1 40
C07 0.1 0
―――――――――――――――

[Table 11]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
15 (0.1) + C07 (0.1) 40 30
9 (0.1) + C07 (0.1) 30 20
4 (0.1) + C07 (0.1) 20 0
20 (0.1) + C07 (0.1) 30 10
23 (0.1) + C07 (0.1) 70 50
10 (0.1) + C07 (0.1) 70 40
―――――――――――――――――――――――

[Table 12]
―――――――――――――――
Compound No. Concentration (ppm) Control Value ―――――――――――――――
15 0.1 60
9 0.1 30
4 0.1 30
20 0.1 20
23 0.1 20
10 0.1 30
E01 0.1 0
―――――――――――――――

[Table 13]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
15 (0.1) + E01 (0.1) 70 60
9 (0.1) + E01 (0.1) 50 30
4 (0.1) + E01 (0.1) 20 30
20 (0.1) + E01 (0.1) 30 20
23 (0.1) + E01 (0.1) 60 20
10 (0.1) + E01 (0.1) 10 30
―――――――――――――――――――――――

[Test Example 2] Nematicidal test against sweet potato root nematode The chemical solution was prepared so as to have a concentration of. 1 ml of the chemical solution was treated on a stock of a plant tray planted spinach seedling (about 2 weeks after germination) filled with 10 g of soil per cell. One hour after the treatment, the stock was inoculated with 1 ml of water containing 2 L larvae of the sweet potato nematode. The number of larvae was 100 per 1 ml of water. It was kept in a greenhouse (temperature 25-35 ° C. for 3 weeks, and the degree of growth of the hump formed at the root was determined according to the following disease index and disease severity.

The efficiency (%) with respect to the untreated section was calculated by the following formula 2. The results are shown in Tables 14 to 21.
[Disease index] 0: No humps are observed, 1: Humps are found in part of the root system, 2: Humps are found in the whole root system, 3: Large humps are found, 4: Large humps are found in the whole root system [Severity] = {Σ (attack index x number of diseased strains by index) / (4 x number of strains)} x 100
efficacy (%) = {1-(Treatment zone disease severity / No treatment zone disease severity)} x 100 (2)
Moreover, the synergistic effect was computed from the control value with respect to each chemical | medical solution density | concentration using the said Colby method.

[Table 14]
―――――――――――――――――――――――
Compound No. Concentration (ppm) Control Value ―――――――――――――――――――――――
15 3 20
9 3 20
4 3 20
20 3 20
23 3 20
10 3 40
―――――――――――――――――――――――

[Table 15]
―――――――――――――――――――――――
Compound No. Concentration (ppm) Control Value ―――――――――――――――――――――――
C07 1 20
C01 1 20
A08 1 20
B05 1 20
E01 1 40
―――――――――――――――――――――――

[Table 16]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
15 (3) + C07 (1) 40 36
15 (3) + C01 (1) 40 36
15 (3) + A08 (1) 60 36
15 (3) + B05 (1) 40 40
15 (3) + E01 (1) 60 36
―――――――――――――――――――――――

[Table 17]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
9 (3) + C07 (1) 50 36
9 (3) + C01 (1) 40 36
9 (3) + A08 (1) 40 36
9 (3) + B05 (1) 60 40
9 (3) + E01 (1) 60 36
―――――――――――――――――――――――

[Table 18]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
4 (3) + C07 (1) 60 36
4 (3) + C01 (1) 40 36
4 (3) + A08 (1) 40 36
4 (3) + B05 (1) 60 40
4 (3) + E01 (1) 80 36
―――――――――――――――――――――――

[Table 19]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
20 (3) + C07 (1) 70 36
20 (3) + C01 (1) 60 36
20 (3) + A08 (1) 60 36
20 (3) + B05 (1) 60 40
20 (3) + E01 (1) 60 36
―――――――――――――――――――――――

[Table 20]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
23 (3) + C07 (1) 60 36
23 (3) + C01 (1) 40 36
23 (3) + A08 (1) 60 36
23 (3) + B05 (1) 60 40
23 (3) + E01 (1) 80 36
―――――――――――――――――――――――

[Table 21]
―――――――――――――――――――――――
Compound No. [Concentration (ppm)] Control Value Theoretical Value ―――――――――――――――――――――――
10 (3) + C07 (1) 40 52
10 (3) + C01 (1) 60 52
10 (3) + A08 (1) 60 52
10 (3) + B05 (1) 40 60
10 (3) + E01 (1) 80 52
―――――――――――――――――――――――

[Test Example 3] Soil blending treatment test for Meloidogyne incognita 6 eggs of sweet potato nematode were mixed per 1 g of soil to prepare test soil. A chemical solution of Compound (I) adjusted to a concentration of 300 ppm according to the formulation example (emulsion) was treated and mixed in an amount of 300 μl per 30 g of test soil. After filling the test soil after chemical solution treatment into the cell tray, cucumber was sown quickly. Twenty-one days after sowing, the control rate (%) for the untreated group was calculated from the degree of root disease (index: 0 to 10). The calculation method is as follows.
E = 100−X / Y × 100
X: Disease index of the treated area Y: Disease index of the untreated area E: Control rate As a result, the compound No. is 4, 8, 9, 10, 11, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 59, 60, 61, 62, 63, 64, 65, 66, 67 and 68 (I) have a control rate (%) of 50% or more at 300 ppm treatment. Indicated.

[Test Example 4] Soil-mixing treatment test for Kitanagusu nematode (Pratylenchus penetrans) An equal amount of steam sterilized soil was mixed into the contaminated soil of Kitanegusu nematode to prepare a test soil. The compound (I) chemical solution adjusted to a concentration of 300 ppm according to the formulation example (emulsion) was treated and mixed at a rate of 400 μl per 40 g of test soil. After filling the test soil after the chemical solution treatment into a falcon tube, burdock was quickly sown. 42 days after sowing, the control rate (%) for the untreated group was calculated from the degree of root disease (index: 0 to 5). The calculation method is as follows.
E = 100−X / Y × 100
X: Disease index in the treated area Y: Disease index in the untreated area E: Control rate As a result, the compound numbers were 10, 22, 25, 26, 27, 28, 29, 35, 36, 40, 42, 49, Compound (I) of 50, 51, 57, 55, 60, 65 and 67 showed a control rate (%) of 50% or more by the 300 ppm treatment.

[Test Example 5] Soil mixing treatment test for soybean cyst nematode (Heterodera glycines) 30 test pieces of soybean cyst nematode eggs per 1 g of soil were mixed. A chemical solution of Compound (I) adjusted to a concentration of 300 ppm according to Formulation Example (emulsion) was treated at 2000 μl per 200 g of test soil and mixed. After filling the test soil after the chemical solution treatment into the pot, soybean was sown quickly. 42 days after sowing, the control rate (%) for the untreated area was calculated from the degree of cyst formation at the root (index: 0 to 5). The calculation method is as follows.
E = 100−X / Y × 100
X: Disease index in the treated area Y: Disease index in the untreated area E: Control rate As a result, the compound numbers were 10, 22, 25, 27, 28, 30, 31, 32, 33, 34, 35, 40, Compound (I) of 42, 49, 51, 54, 57, 60, 65 and 67 showed a control rate (%) of 50% or more at 300 ppm treatment.

[Test Example 6] Seed treatment test for Meloidogyne incognita Compound (I) was dissolved in acetone and smeared to a treatment dose of 300 mg per cucumber seed. On the other hand, 18 eggs of sweet potato nematode were mixed per 1 g of soil to prepare test soil. The test soil was filled in a cell tray, and seeded with cucumber seeds treated with chemicals one by one. The raw weight of the above-ground part was investigated 21 days after sowing, and the growth promotion effect rate (%) relative to the untreated area was calculated. The calculation method is as follows.
E = X / Y × 100-100
X: Raw weight of A treatment area Y: Raw weight of untreated area E: Growth promotion effect rate As a result, compound No. was 4, 10, 11, 21, 22, 27, 28, 30, 31, 36, 37, 40, 43, 45, 47, 48, 50, 51, 53, 57, 60, 61, 62, 63, 64, 65 and 68 compounds (I) are more than 20% at 300 mg / seed treatment Growth promotion effect (%) was shown.

[Test Example 7] Irrigation treatment test for Meloidogyne incognita A stock tray of spinach-planted spinach seedlings filled with 10 g of soil was infused and inoculated with 1 ml of water containing 2 L larvae of root-knot nematodes. The number of larvae was 100 per 1 ml of water. One hour after inoculation, 1 ml of the chemical solution of Compound (I) adjusted to a concentration of 300 ppm according to the formulation example (emulsion) was treated to the stock company. Three weeks after the treatment, the control rate (%) for the untreated area was calculated from the degree of root disease (index: 0 to 10).
As a result, Compound No. was 4, 8, 9, 10, 11, 15, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36 , 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 59, 60, 61, 62 , 63, 64, 65, 66, 67 and 68 (I) showed a control rate (%) of 50% or more at 300 ppm treatment.

[Test Example 8] Plant hole treatment test for Meloidogyne incognita Six eggs of sweet potato nematode were mixed per 1 g of soil to prepare test soil. The test soil was filled in a cell tray, and 1 ml of a chemical solution of Compound (I) adjusted to a concentration of 300 ppm according to the formulation example (emulsion) was irrigated for each planting hole, and cucumber was quickly seeded. 21 days after sowing, the control rate (%) for the untreated area was calculated from the degree of root disease (index: 0 to 10).
As a result, compound Nos. 4, 9, 10, 15, 20, 22, 27, 41, 42, 49, 51, 60, 65 and 68 (I) were controlled at a concentration of 300 ppm by 50% or more. Rate (%).

The composition of the present invention and the control method of the present invention exhibit a synergistic and excellent control effect on various nematodes and can be used in the field of agriculture and horticulture.
The entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2014-0668010 filed on March 28, 2014 are incorporated herein as the disclosure of the specification of the present invention. Is.

Claims (25)

1. A nematicidal composition comprising an oxime-substituted amide compound represented by formula (I), an N-oxide thereof or a salt thereof as an active ingredient.
   

   

   [Wherein G ¹ is G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7, G ¹ -8, G ¹ -9, G ¹ -11, G ¹ -12, G ¹ -13, G ¹ -16, G ¹ -27, G ¹ -32, G ¹ -33 or G ¹ -50,
   

   

   G ² represents the structure of G ² -1, G ² -2, G ² -6 or G ² -9,
   

   

   W represents an oxygen atom or a sulfur atom,
   X ¹ represents a halogen atom, nitro, methyl, ethyl or C ₁ -C ₂ haloalkyl,
   X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure represented by G ¹ -27 and X ¹ represents dihalomethyl, X ² represents a hydrogen atom. ,
   X ³ represents a hydrogen atom, methyl or ethyl,
   X ⁴ represents a hydrogen atom,
   X ⁵ represents a hydrogen atom, a fluorine atom or a chlorine atom,
   Y ¹ represents a hydrogen atom, a halogen atom, methyl, trifluoromethyl or methoxy,
   Y ² represents a hydrogen atom, a halogen atom, cyano, C ₁ -C ₃ alkoxy or methylthio,
   Y ³ is optionally substituted by a hydrogen atom, a halogen atom, cyano, C ₁ -C ₄ alkyl, trifluoromethyl, C ₂ -C ₄ alkenyl, C ₂ -C ₆ alkynyl, R ⁶ (C ₂ -C ₆ ) represents alkynyl, —OR ⁷ , C ₁ -C ₄ alkylthio, —C (R ⁸ ) = NOR ⁹ , phenyl, D-3 or D-7,
   Y ⁴ represents a hydrogen atom or a halogen atom,
   Y ⁵ represents a hydrogen atom,
   R ¹ is, C ₁ ~ C ₆ alkyl, C ₁ ~ C ₄ haloalkyl, substituted by _{^{R 10 (C 1 ~ C 4}} ) alkyl, C ₃ ~ C ₆ cycloalkyl, C ₃ ~ C ₆ alkenyl, C ₃ Represents -C ₄ haloalkenyl, C ₃ -C ₆ alkynyl or phenyl;
   R ² is a hydrogen atom, methyl or ethyl, provided that represents a structure in which G ¹ is represented by ^{G 1} -1, X ¹ represents a chlorine atom, is X ^2, X ^3, X ⁴ and ^{X 5} In the case where it represents a hydrogen atom, G ² represents a structure represented by G ² -1, Y ³ represents a chlorine atom, and Y ¹ , Y ² , Y ⁴ and Y ⁵ represent a hydrogen atom, R ² represents methyl or ethyl;
   R ³ represents a hydrogen atom or methyl, or R ³ together with R ² forms an ethylene chain to form a cyclopropyl ring with the carbon atom to which R ² and R ³ are bonded. Represents
   R ⁴ represents a hydrogen atom, cyclopropyl, C ₁ -C ₂ alkoxy, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl,
   R ⁵ represents methyl or ethyl,
   R ⁶ represents a halogen atom, C ₃ -C ₆ cycloalkyl, hydroxy (C ₃ -C ₆ ) cycloalkyl, C ₅ -C ₆ cycloalkenyl, —OH, —OR ⁷ , C ₁ -C ₄ alkylcarbonyloxy, C ₁ -C ₄ alkylsulfonyloxy, C ₁ -C ₄ alkylthio, trimethylsilyl, -C (R ⁸ ) = NOR ⁹ , phenyl, phenyl substituted by (Z) _m or D-32,
   Z represents a halogen atom, cyano, nitro, C ₁ -C ₄ alkyl, trifluoromethyl, methoxy, trifluoromethoxy, trifluoromethylthio or phenyl, and when m or n represents 2 or more, each Z May be the same as or different from each other, and when two Zs are adjacent to each other, the two adjacent Zs form -CH = CH-CH = CH- A 6-membered ring may be formed together with the carbon atom to which Z of
   R ⁷ is substituted by C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy (C ₁ -C ₂ ) alkyl, E-14, C ₃ -C ₄ alkynyl or (Z) _m Represented phenyl,
   R ⁸ represents a hydrogen atom or methyl,
   R ⁹ represents methyl or ethyl,
   R ¹⁰ is cyano, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, E-5, E-9, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, trimethylsilyl, -C ( R ¹¹ ) = NOR ¹² , phenyl, phenyl substituted by (Z) _m , D-10 or D-32;
   D-3, D-7, D-10 and D-32 each represent an aromatic heterocycle having the following structural formula;
   

   

   E-5, E-9 and E-14 each represent a saturated heterocyclic ring of the following structural formula,
   

   

   R ¹¹ represents methyl,
   R ¹² represents methyl or ethyl,
   m represents an integer of 1, 2 or 3,
   n represents an integer of 0, 1 or 2. ]
2. G ¹ is G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7, G ¹ -11, G ¹ -12, G ¹ -16, G ¹ -27, or G ¹ -33 Represents
   G ² represents the structure of G ² -1, G ² -2 or G ² -9,
   W represents an oxygen atom,
   X ¹ represents a halogen atom, nitro, methyl, difluoromethyl or trifluoromethyl,
   X ² represents a hydrogen atom, a fluorine atom or a chlorine atom, provided that when G ¹ represents a structure of G ¹ -27 and X ¹ represents difluoromethyl, X ² represents a hydrogen atom,
   X ³ represents a hydrogen atom or methyl,
   Y ¹ represents a fluorine atom, a chlorine atom or a bromine atom,
   Y ² represents a hydrogen atom, a fluorine atom, a chlorine atom, cyano, C ₁ -C ₃ alkoxy or methylthio,
   Y ³ is a halogen atom, trifluoromethyl, C ₂ -C ₄ alkenyl, C ₂ -C ₆ alkynyl, (C ₂ -C ₆ ) alkynyl optionally substituted by R ⁶ , C ₁ -C ₄ haloalkoxy or -C (R ⁸ ) = NOR ⁹
   Y ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom,
   R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl substituted by R ¹⁰ , C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ Represents -C ₄ haloalkenyl or C ₃ -C ₆ alkynyl,
   R ² represents a hydrogen atom or methyl, provided that when G ² represents a structure represented by G ² -1, R ² represents methyl;
   R ³ represents a hydrogen atom, or R ³ together with R ² forms an ethylene chain, thereby forming a cyclopropyl ring with the carbon atom to which R ² and R ³ are bonded. ,
   R ⁴ represents a hydrogen atom, cyclopropyl or methoxy,
   R ⁵ represents methyl,
   R ⁶ represents a halogen atom, C ₃ -C ₆ cycloalkyl, —OR ⁷ , trimethylsilyl, —C (R ⁸ ) ═NOR ⁹ or phenyl,
   R ⁷ represents C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxymethyl;
   R ¹⁰ represents C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl, trimethylsilyl, phenyl, phenyl substituted by (Z) _m or D-32;
   Z represents a halogen atom or cyano, and when m represents 2 or more, each Z may be the same as or different from each other;
   The nematicidal composition according to claim 1, wherein n represents an integer of 1.
3. G ¹ represents the structure of G ¹ -1, G ¹ -2, G ¹ -3, G ¹ -7 or G ¹ -11;
   G ² is, represents the structure of G ² -1 or ^{G 2} -2,
   X ¹ represents a halogen atom, methyl, difluoromethyl or trifluoromethyl,
   X ² represents a hydrogen atom or a fluorine atom,
   X ³ represents a hydrogen atom,
   X ⁵ represents a hydrogen atom or a fluorine atom,
   Y ¹ represents a chlorine atom or a bromine atom,
   Y ² represents a hydrogen atom,
   Y ³ represents a halogen atom, trifluoromethyl, cyclopropylethynyl or C ₁ -C ₄ haloalkoxy,
   Y ⁴ represents a hydrogen atom,
   R ¹ represents C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, (C ₁ -C ₄ ) alkyl or C ₃ -C ₆ alkenyl substituted by R ¹⁰ ,
   R ⁴ represents a hydrogen atom,
   R ¹⁰ represents C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl or phenyl substituted by (Z) _m ,
   Z represents a halogen atom or cyano, and when m represents 2, each Z may be the same as or different from each other;
   The nematicidal composition according to claim 2, wherein m represents an integer of 1 or 2.
4. G ¹ represents the structure of G ¹ -1,
   X ¹ represents a halogen atom, methyl or trifluoromethyl,
   X ² represents a hydrogen atom or a fluorine atom,
   X ³ represents a hydrogen atom,
   X ⁴ represents a hydrogen atom,
   The nematicidal composition according to claim 3, wherein X ⁵ represents a hydrogen atom or a fluorine atom.
5. G ¹ represents the structure of G ¹ -2,
   X ¹ represents a chlorine atom or trifluoromethyl,
   The nematicidal composition according to claim 3, wherein X ³ , X ⁴ and X ⁵ represent a hydrogen atom.
6. G ¹ represents the structure of G ¹ -3,
   X ¹ represents a chlorine atom, difluoromethyl or trifluoromethyl,
   The nematicidal composition according to claim 3, wherein X ² , X ³ and X ⁴ represent a hydrogen atom.
7. G ¹ represents the structure of G ¹ -7,
   X ¹ represents trifluoromethyl,
   The nematicidal composition according to claim 3, wherein X ³ and X ⁴ represent a hydrogen atom.
8. G ¹ represents the structure of G ¹ -11,
   X ¹ represents methyl,
   The nematicidal composition according to claim 3, wherein X ³ and X ⁴ represent a hydrogen atom.
9. G ² is, represents the structure of G ² -2,
   Y ¹ represents a chlorine atom or a bromine atom,
   Y ² represents a hydrogen atom,
   Y ³ represents a fluorine atom, a chlorine atom, a bromine atom, trifluoromethyl, cyclopropylethynyl or C ₁ -C ₄ haloalkoxy.
   The nematicidal composition according to claim 3, wherein Y ⁴ represents a hydrogen atom.
10. A nematicidal composition comprising a synergistically effective amount of the following active ingredient A and the following active ingredient B:
    Active component A: One or more compounds selected from the group consisting of the oxime-substituted amide compound represented by formula (I) according to claim 1, its N-oxide, and salts thereof.
    Active ingredient B: one or two selected from the group consisting of BI group, B-II group, B-III group, B-IV group, BV group, B-VI group, B-VII group and B-VIII group The above compound.
    BI group: Benomyl, Carbofuran, Chloetocarb, Carbosulfuran, Alanicarb, Aldicarb, Aldoxycarb, Oxamyl, Tile Pate.
    Group B-II: diamidafos, phenamifos, phostietane, phosphamidon, imisiaphos, mecalphone.
    Group B-III: Kazusafos, Chlorpyrifos, Diclofenthion, Dimethoate, Etoprofos, Fensulfothione, Phosthiazate, Heterophos, Isamidophos, Isazofos, Forate, Phosphocarb, Terbufos, Thionazine, Triazophos.
    Group B-IV: disulfide, cyanogen, 1,2 dichloropropane, 1,3 dichloropropene, dithioether, methyl bromide, methyl iodate, tetrathiocarbonite sodium salt.
    BV group: Abamectin, Carbachol, Acetoprole, Benclothiaz, Chloropicrin, Daazomet, Divisipi, Disiaipi, Fluenesulfone, Fafural, Metam, Methyl isothiocyanate, Thioxazafen, Xylenols, Triazophos, Sclareol, Chloranthraniprole, Cyantrani Liprol, cyclaniliprol, iprodione, AKD-1193 (trial name).
    Group B-VI: Pasteuria bacteria, Pasteuria penetrans, Pasteuria ramosa, Pasteuria solnai, Pasteurian nisawae.
    Group B-VII: sulfur, lime sulfur mixture, basic copper sulfate, iprovenfos, edifenphos, toluclofos methyl, thiram, polycarbamate, dinebu, manzeb, mancozeb, propineb, thiophanate, thiophanate methyl, iminoctadine acetate, iminoctadine albe Silates, mepronil, flutolanil, pencyclon, furamethpyr, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanide, fursulfamide, chlorothalonil, cresoxime methyl, phenoxanyl, himexazole, ecromezol, fluorimido, procimidone, vinclozoline, fluclozoline, fludiazol Zole, ipconazole, fluconazole, propiconazole, difenoconazole, microbe Nil, tetraconazole, hexaconazole, tebuconazole, thiazinyl, imibenconazole, prochloraz, pefrazoate, cyproconazole, isoprothiolane, phenalimol, pyrimethanyl, mepanipyrim, pyrifenox, fluazinam, trifolin, dichromedin, azoxystrobin, thiadiazine , Captan, probenazole, acibenzoral S methyl, fusaride, tricyclazole, pyroxylone, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin, fluazinam, triclamid, amisulbrom.
    Group B-VIII: Sienopyrafen, Ethion, Trichlorfone, Metamidophos, Acephate, Dichlorvos, Mevinfos, Monocrotofos, Malathion, Formothione, Mecarbam, Bamidthione, Thiometone, Disulfotone, Oxydeprophos, Nared, Methylparathion, Fenitrothion, Cyanophos, Propaphos, Fentione Prothiophos, Profenofos, Isophenphos, Temefos, Fentoate, Dimethylvinphos, Chlorfevinphos, Tetrachlorbinphos, Hoxime, Isoxathion, Pyraclofos, Methidathion, Chloropyphos, Pyridaphenthion, Diazinon, Pirimiphosmethyl, Hosalon, Phosmet, Dioxabenzophos, Quinalphos , Mesulfenphos, DPS, isoamidophos, enaprophos, Enthion, Sulprofos, Pyrethrin, Allethrin, Praretrin, Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropatrine, Cypermethrin, Alpha cypermethrin, Cyhalothrin, Lambdacyhalothrin, Deltamethrin, Acrinatrin, Fenvalerate, Esfenvalerate, Cysprovalerate , Etofenprox, halfenprox, silafluophene, flucitrinate, fulvalinate, mesomil, thiodicarb, cartap, metorcarb, xylcarb, propoxyl, phenoxycarb, fenobucarb, etiofencarb, phenothiocarb, bifenazete, BPMC, carbaryl, pyrimibencarb, furathiocarb , Diafenthiuron, difluve Duron, teflubenzuron, hexaflumuuron, novallon, rufenuron, flufenoxuron, chlorfluazuron, fenbutane oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, metoprene, hydroprene, vinapacryl, amitraz, dichor, kelsen , Chlorbenzilate, phenisobromolate, tetradiphone, bensultap, benzomate, tebufenozide, methoxyphenozide, pyridalyl, metaflumizone, flubendiamide, chromafenozide, propargite, acequinosyl, endosulfan, diofenolan, chlorfenapyrazole, fenpyroximate, tolfenpyrazole , Hexythiazox, Nicotine sulfate, nitenpyram, acetamiprid, thiacloprid, imidacloprid, thiamethoxam, clothianidin, dinotefuran, pyriproxyfen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC, pymetrozine, clofentezine, buprofezin, thiocyclam, phenazaquin, indoxameb , Polynactin complex, milbemectin, emamectin benzoate, spinosad, BT, azadirachtin, rotenone, hydroxypropyl starch, levamisole hydrochloride, morantel tartrate, monacrosporium fimatopagum.
11. The nematicidal composition according to claim 10, comprising an active ingredient B selected from the B-I group.
12. The nematicidal composition according to claim 10, comprising an active ingredient B selected from the B-II group.
13. The nematicidal composition according to claim 10, comprising an active ingredient B selected from the B-III group.
14. The nematicide composition according to claim 10, comprising an active ingredient B selected from the B-IV group.
15. The nematicidal composition according to claim 10, comprising an active ingredient B selected from the B-V group.
16. The nematicide composition according to claim 10, comprising an active ingredient B selected from the B-VI group.
17. The nematicide composition according to claim 10, comprising an active ingredient B selected from the B-VII group.
18. The nematicidal composition according to claim 10, comprising an active ingredient B selected from the B-VIII group.
19. The nematicidal composition according to any one of claims 1 to 18, wherein 0.001 to 1000 parts by weight of the active ingredient B is contained per 1 part by weight of the active ingredient A.
20. One or more active ingredients A according to claim 10 and one or more active ingredients B according to claim 10 are treated simultaneously or close in time. And the nematode control method.
21. A method for controlling nematodes, which comprises treating the nematicidal composition according to any one of claims 1 to 19 with soil.
22. The treatment amount of active ingredient A is 0.1 to 1000 ga.i./ha, and the treatment amount of active ingredient B is 0.1 to 1000 ga.i./ha. Control method.
23. The control method according to claim 20 or 21, wherein the amount of applied medicine is 0.005 to 50 kg per hectare as the amount of active ingredient.
24. A method for controlling nematodes, which comprises treating a seed of a plant with the nematicidal composition according to any one of claims 1 to 19.
25. A method for controlling nematodes, comprising treating the nematicidal composition according to any one of claims 1 to 19 in a nursery box.