WO2017170743A1 - Composition nématicide et procédé de lutte contre les nématodes - Google Patents

Composition nématicide et procédé de lutte contre les nématodes Download PDF

Info

Publication number
WO2017170743A1
WO2017170743A1 PCT/JP2017/013020 JP2017013020W WO2017170743A1 WO 2017170743 A1 WO2017170743 A1 WO 2017170743A1 JP 2017013020 W JP2017013020 W JP 2017013020W WO 2017170743 A1 WO2017170743 A1 WO 2017170743A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
halo
atom
active ingredient
Prior art date
Application number
PCT/JP2017/013020
Other languages
English (en)
Japanese (ja)
Inventor
穂高 今仲
紀彦 三森
国光 中平
基悦 岩佐
Original Assignee
日産化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP2017012004A external-priority patent/JP2019094264A/ja
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2017170743A1 publication Critical patent/WO2017170743A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides

Definitions

  • the present invention relates to a novel plant parasitic nematode control composition
  • a novel plant parasitic nematode control composition comprising specific oxime-substituted amide compounds, their N-oxides or salts thereof, and specific fungicidal, bactericidal, insecticidal or acaricidal active compounds. And a control method.
  • the oxime-substituted amide compound represented by the formula (I) which is the first active ingredient compound, their N-oxides or salts thereof are known and their pest control agents Is known (for example, see Patent Document 1).
  • the compound described as the active ingredient B which is the second active ingredient in the nematicidal composition of the present invention is a compound having a known bactericidal, bactericidal, insecticidal or acaricidal activity (for example, (Refer nonpatent literature 1.).
  • a bactericidal or bactericidal composition containing a certain oxime-substituted amide compound and a compound having a known bactericidal or bactericidal activity see, for example, Patent Document 2
  • a nematicidal composition containing a compound having a known nematicidal activity for example, see Patent Document 3 is known.
  • Plant nematode damage caused by infection of various nematodes on cereals, fruit trees, vegetables, ornamental plants, etc. is a serious damage such as a decrease in the quality of crops, a significant decrease in yield, and in some cases withering of plants.
  • causes significant economic losses not only to producers but also to consumers. Therefore, effective control of these plant nematodes is an extremely important issue in order to achieve efficient and stable production of agricultural crops. From such a viewpoint, conventionally, development of a control agent for the purpose of controlling plant parasitic nematodes has progressed, and many effective agents have been put to practical use until now.
  • the present inventors have shown excellent plant parasitic nematode control activity and non-targets such as plants, mammals, fish, useful insects and natural enemies
  • the present invention has been completed by finding that the composition containing the compound having an activity together has surprisingly excellent synergistic nematicidal effect that cannot be predicted from the case of using each of them alone. .
  • the present invention includes the following compositions [1] to [34] (hereinafter referred to as the present composition), [35] to [38] control methods (hereinafter referred to as the present method), [ [39] to [83] (hereinafter referred to as the compound of the present invention) and [84] to [87].
  • An active ingredient B comprising the following active ingredient A and one or more compounds selected from the group consisting of the following BI group, BX group, CI group, and C-XIV group And a composition for nematicides, each containing a synergistically effective amount.
  • Active ingredient A an oxime-substituted amide compound represented by the following formula (I) or an N-oxide or a salt thereof.
  • G 1 represents a structure represented by G 1 -1 or G 1 -2 below,
  • G 2 represents a structure represented by the following G 2 -1, G 2 -2 or G 2 -3,
  • W represents an oxygen atom or a sulfur atom
  • X 1 represents a halogen atom, nitro, methyl, difluoromethyl, trifluoromethyl or —S (O) r X 1a
  • X 1a represents C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 3 -C 6 alkenyl or benzyl
  • Y 1 represents a hydrogen atom, a halogen atom, methyl, trifluoromethyl or methoxy
  • Y 2 represents a hydrogen atom, a halogen atom, cyano, methoxy or methylthio
  • Y 3 is optionally substituted by a hydrogen atom, halogen atom, cyano, C 1 -C 4 alkyl, trifluoromethyl, C 2 -C 4 alkenyl, C 2 -C 6 alkynyl, R 6 (C 2 -C 4 6 ) represents alkynyl,
  • a 6-membered ring may be formed with the carbon atom to which Z of R 7 is C 1 -C 4 alkyl, halo (C 1 -C 4 ) alkyl, C 1 -C 4 alkoxy (C 1 -C 2 ) alkyl, E-3, C 3 -C 4 alkynyl or (Z) represents phenyl substituted by m ;
  • R 8 represents a hydrogen atom or methyl;
  • R 9 represents methyl or ethyl,
  • E-1, E-2 and E-3 each represent a saturated heterocyclic ring represented by 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; r represents an integer of 0, 1 or 2. ]
  • Active ingredient B BI group: metalaxyl, oxolinic acid.
  • Group B-II benomyl, ethaboxam, pencicuron, fluopicolide, diflumetorim, thiophanate-methyl.
  • B-III group thifluzamide, azoxystrobin, amisulbrom, fluazinam, ametoctradin, cyazofamid, flutolanil, mepronil, triproxil Strobibin (trifloxystrobin), fluxapyroxad (fluxapyroxad).
  • B-IV group cyprodinil, kasugamycin, oxytetracycline.
  • BV group fludioxonil, iprodione.
  • Group B-VI isoprothiolane, propamocarb hydrochloride, tolclofos-methyl.
  • Group B-VII tebuconazole, fenhexamid, prochloraz, pefurazoate, difenoconazole, ipconazole, simeconazole.
  • B-VIII group validamycin, dimethomorph, polyoxins.
  • Group B-IX tricyclazole, diclocymet.
  • BX group fosetyl-aluminium, chlorothalonil, captan, mancozeb.
  • CI group fipronil.
  • C-II group bifenthrin, indoxacarb, etofenprox, cypermethrin.
  • Group C-III imidacloprid, spinosyn, cartap, acetamiprid, clothianidin, dinotefuran, nitenpyram, thiamethoxam.
  • Group C-IV amitraz.
  • CV group acequinocyl, cyenopyrafen, pyridaben, chlorfenapyr, tetradifon.
  • C-VI group tebufenozide, cyromazine, lufenuron, buprofezin.
  • Group C-VII spirotetramat.
  • Group C-VIII chlorantraniliprole, cyantraniliprole.
  • Group C-IX phenoxycarb.
  • CX group etoxazole.
  • C-XI group Pymetrozine.
  • C-XII group bifenazate.
  • C-XIII group Bacillus thuringiensis.
  • C-XIV group DMTP (DMTP), acephate, chlorpyrifos, prothiofos.
  • G 1 represents a structure represented by G 1 -2
  • G 2 represents a structure represented by G 2 -1 or G 2 -2
  • X 1 represents a chlorine atom, an iodine atom, methyl, difluoromethyl, trifluoromethyl or —S (O) r X 1a
  • Y 1 represents a chlorine atom
  • Y 2 represents a hydrogen atom
  • Y 3 represents a chlorine atom, a bromine atom, cyano, trifluoromethyl, C 2 -C 6 alkynyl, cyclopropylethynyl or halo (C 1 -C 4 ) alkoxy
  • Y 4 represents a hydrogen atom
  • R 1 is, C 1 ⁇ C 4 alkyl, halo (C 1 ⁇ C 4) alkyl
  • G 1 represents a structure represented by G 1 -2
  • G 2 represents a structure represented by G 2 -2
  • X 1 represents a chlorine atom, difluoromethyl, trifluoromethyl or methylsulfonyl
  • Y 3 represents a chlorine atom, a bromine atom, cyano, C 2 -C 6 alkynyl or cyclopropylethynyl
  • R 1 is substituted by C 1 ⁇ C 4 alkyl, halo (C 1 ⁇ C 4) alkyl or R 10 (C 1 ⁇ C 4 ) alkyl
  • R 10 represents halo (C 3 -C 6 ) cycloalkyl.
  • active ingredient B is a compound selected from the CI group to C-XIV group.
  • active ingredient B is a compound selected from the BI group.
  • active ingredient B is a compound selected from the group B-II.
  • the nematicide for use according to any one of [1] to [30] above which contains 0.1 to 10 parts by weight of active ingredient B with respect to 1 part by weight of active ingredient A Composition.
  • a method for controlling nematodes characterized in that the treatment is performed simultaneously or close in time.
  • a method for controlling nematodes wherein the composition for nematicidal insects according to any one of [1] to [34] above is sprayed on a plant.
  • a method for controlling nematodes which comprises treating the nematocidal composition according to any one of [1] to [34] above on a soil in which plants are grown.
  • a method for controlling nematodes wherein the composition for nematicides according to any one of [1] to [34] above is treated on plant seeds, tuberous roots and rhizomes.
  • a 1 , A 2 and A 3 each independently represent CH or a nitrogen atom, provided that one of A 1 and A 2 represents a nitrogen atom, W represents an oxygen atom or a sulfur atom, Y 1 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl, Y 2 represents a hydrogen atom, a halogen atom or cyano, Y 3 is a halogen atom, cyano, halo (C 1 -C 6 ) alkyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted by R 6 , C 1 -C 6 alkoxy or Represents halo (C 1 -C 6 ) alkoxy, Y 4 represents a hydrogen atom or a halogen atom, R 1 is, C 1 ⁇ C 6 alkyl, halo (C 1 ⁇ C 6) alkyl, optionally substituted by R 10 (C 1
  • a 1 and A 3 represent a nitrogen atom
  • a 2 represents CH
  • W represents an oxygen atom
  • Y 1 represents a halogen atom
  • Y 2 and Y 4 represent a hydrogen atom
  • Y 3 represents a halogen atom, cyano, halo (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkynyl optionally substituted by R 6
  • R 3 represents a hydrogen atom
  • R 6 represents C It represents 3 ⁇ C 6 cycloalkyl
  • Z represents a halogen atom or cyano
  • X 1a represents an oxime-substituted amide compound according to the above [36], wherein C 1 -C 6 alkyl or halo (C 1 -C 6 ) alkyl, or an N-oxide or a salt thereof.
  • Y 3 is, R 1 represents a halogen atom, C 1 ⁇ C 6 alkyl, halo (C 1 ⁇ C 6) alkyl, substituted with R 10 (C 1 ⁇ C 6 ) alkyl or C 3 ⁇ It represents a C 6 alkenyl, X 1a represents C 1 -C 6 alkyl, and r represents 2 The oxime-substituted amide compound or its N-oxide or salt thereof according to [40] above. [42] A 1 represents a nitrogen atom, The oxime-substituted amide compound according to any one of the above [39] to [41], wherein A 2 and A 3 represent CH, or an N-oxide thereof or a salt thereof.
  • a 1 represents CH, The oxime-substituted amide compound according to any one of the above [39] to [41], wherein A 2 and A 3 represent a nitrogen atom, or an N-oxide or a salt thereof.
  • a 1 and A 2 represent a nitrogen atom, The oxime-substituted amide compound or the N-oxide or salt thereof according to any one of the above [39] to [41], wherein A 3 represents CH.
  • a 1 and A 3 represent a nitrogen atom, The oxime-substituted amide compound according to any one of the above [39] to [41], wherein A 2 represents CH, or an N-oxide thereof or a salt thereof.
  • a 1 and A 3 represent CH, The oxime-substituted amide compound according to any one of the above [39] to [41], wherein A 2 represents CH, or an N-oxide thereof or a salt thereof.
  • a 1 and A 3 represent CH, The oxime-substituted
  • Y 3 is halo (C 1 -C 6 ) alkyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl, C 1 -C 6 alkoxy or halo optionally substituted by R 6
  • Y 4 represents a hydrogen atom.
  • R 1 is, C 1 ⁇ C 6 alkyl, halo (C 1 ⁇ C 6) alkyl, optionally substituted by R 10 (C 1 ⁇ C 6 ) alkyl, C 3 ⁇ C 6 alkenyl, halo
  • R 10 C 1 ⁇ C 6 alkyl, C 3 ⁇ C 6 alkenyl, halo
  • the oxime-substituted amide compound or the N-oxide thereof according to any one of the above [39] to [58], which represents C 3 -C 6 ) alkenyl, C 3 -C 6 alkynyl or halo (C 3 -C 6 ) alkynyl Or its salt.
  • R 1 represents C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkyl or C 3 -C 6 alkenyl optionally substituted with R 10 [39] to [58]
  • R 10 represents C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkyl or C 3 -C 6 alkenyl optionally substituted with R 10 [39] to [58]
  • the oxime-substituted amide compound or N-oxide or salt thereof according to any one of items [39] to [58].
  • R 1 represents C 1 -C 6 alkyl.
  • R 1 represents halo (C 1 -C 6 ) alkyl, or an N-oxide thereof or a salt thereof.
  • R 1 is oxime-substituted amide compound according to any one above [39] - [58] representing the optionally substituted (C 1 - C 6) alkyl by R 10 or a N- oxide or Its salt.
  • Z is cyano, nitro, C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 1 -C 6 alkoxy, halo (C 1 -C 6 ) alkoxy or halo (C 1 -C 6 )
  • the oxime-substituted amide compound or the N-oxide or salt thereof according to any one of the above [39] to [71], which represents alkylthio.
  • X 1a represents C 2 -C 6 alkyl, The oxime-substituted amide compound or the N-oxide or salt thereof according to any one of the above [39] to [79], wherein r represents an integer of 0, 1 or 2.
  • X 1a represents halo (C 1 -C 6 ) alkyl; The oxime substituted amide compound according to any one of the above [39] to [79], wherein r represents an integer of 0, 1 or 2, or an N-oxide thereof or a salt thereof.
  • X 1a represents C 3 -C 6 alkenyl or benzyl, The oxime substituted amide compound according to any one of the above [39] to [79], wherein r represents an integer of 0, 1 or 2, or an N-oxide thereof or a salt thereof.
  • a composition for nematicides containing as an active ingredient at least one selected from the oxime-substituted amide compound according to any one of [39] to [83] above, or an N-oxide thereof or a salt thereof.
  • the nematicide composition of the present invention and the nematode control method using the composition of the present invention exhibit an excellent synergistic control effect against plant growth damage caused by various nematodes, as well as existing plant parasites. It also exhibits a sufficient synergistic control effect against nematodes that have acquired resistance to the sex nematode control agent. Therefore, the present invention can provide a useful novel nematicidal composition and an effective nematode control method using the composition of the present invention.
  • the oxime-substituted amide compound represented by the formula (I) used as the active ingredient A of the present invention has E-form and Z-form geometric isomers, and the active ingredient A of the present invention (also referred to as active compound A).
  • the compound used as “)” includes the E-form, the Z-form, or a mixture containing the E-form and the Z-form in an arbitrary ratio.
  • the compound represented by the formula (I) used as the active component A of the present invention depending on the substituent, there is an optically active substance resulting from the presence of one or more asymmetric carbon atoms.
  • the compound used as the active ingredient A of the present invention includes all optically active substances or racemates.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl Specific examples include a group, isobutyl group, s-butyl group, tert-butyl group, pentyl group, 1-ethylpropyl group, 2,2-dimethylpropyl group, hexyl group, and the like. Selected by range.
  • sec- means secondary
  • tert- means tertiary, and the same applies to the following.
  • halo (C a -C b ) alkyl is a linear or branched chain having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • fluoromethyl group 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- Fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 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-tri
  • 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 for each specified number of carbon atoms.
  • halo (C a -C b ) cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • Monocyclic or complex ring structures from 3 to 10 membered rings can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms.
  • 1-fluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dichloro-3-methylcyclopropyl group, 2-bromo-1-ethylcyclobutyl group, 2,2,3,3 -Tetrafluorocyclobutyl group, 2-chlorocyclopentyl group, 3-bromocyclopentyl group, 2,2-difluoro-3-methylcyclopentyl group, 2-iodocyclohexyl group, 3-chlorocyclohexyl group, 4,4-difluorocyclohexyl group Etc. are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenyl refers to an unsaturated carbonization having a linear or branched chain consisting of a to b carbon atoms and having one or more double bonds in the molecule.
  • Specific examples include a 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.
  • halo (C a -C b ) alkenyl is a linear or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And 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.
  • C a -C b cycloalkenyl represents a cyclic hydrocarbon group having a carbon number of a to b 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.
  • 1-cyclobutenyl group, 1-methyl-2-cyclobutenyl group, 1-cyclopentenyl group and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynyl refers to an unsaturated hydrocarbon having a linear or branched chain composed of a to b carbon atoms and having one or more triple bonds in the molecule.
  • ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl Specific examples include a 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. Selected within the specified number of carbon atoms.
  • halo (C a -C b ) alkynyl is linear or branched 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 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.
  • 3-chloro-2-propynyl group, 4-bromo-3-butyn-2-yl group, 4-fluoro-2-butynyl group, 4,4-difluoro-2-butynyl group, 4-iodo-3-butynyl Specific examples include a group, a 4-fluoro-4-methyl-2-pentynyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • 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 a butyloxy group, an isobutyloxy group, an s-butyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkoxy 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 chlorodifluoro group.
  • Methoxy 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 1,2,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylthio represents an alkyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms.
  • methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group Specific examples include a 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.
  • halo (C a -C b ) alkylthio represents a haloalkyl-S— group having the above-mentioned meanings consisting of a to b carbon atoms, such as difluoromethylthio group, trifluoromethylthio group, chlorodifluoro Methylthio group, trichloromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoro Ethylthio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoro Specific examples include methyl) ethylthio group, nonafluorobutyl
  • C a -C b alkylsulfonyl represents an alkyl-S (O) 2 — group having the above-mentioned meanings consisting of a to b carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propyl
  • a sulfonyl 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.
  • tri (C a -C b alkyl) silyl is the same as or different from each other, and the silyl group substituted by the alkyl group having the above-mentioned meanings consisting of a to b carbon atoms
  • Specific examples include trimethylsilyl group, triethylsilyl group, tri (propyl) silyl group, ethyldimethylsilyl group, propyldimethylsilyl group, butyldimethylsilyl group, isobutyldimethylsilyl group, tert-butyldimethylsilyl group and the like. Selected within a range of each specified number of carbon atoms.
  • C a -C b alkylcarbonyl represents an alkyl-C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, acetyl group, propionyl group, butyryl group, isobutyryl group. Specific examples include a 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.
  • C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, Specific examples include a propyloxycarbonyl 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.
  • C a -C b alkylcarbonyloxy represents an alkyl-C (O) —O— group having the above-mentioned meanings consisting of a to b carbon atoms, such as an acetoxy group, propionyloxy group, etc. are given as specific examples and are selected within the range of each designated number of carbon atoms.
  • C a -C b alkylsulfonyloxy represents an alkyl-S (O) 2 —O— group having the above-mentioned meanings consisting of a to b carbon atoms, such as methylsulfonyloxy group, ethyl Specific examples include sulfonyloxy group, propylsulfonyloxy group, isopropylsulfonyloxy group, butylsulfonyloxy group, isobutylsulfonyloxy group, s-butylsulfonyloxy group, tert-butylsulfonyloxy group, and the like. It is selected in the range of the number of atoms.
  • hydroxy (C a ⁇ C b) alkyl "substituted by R 10 (C a ⁇ C b ) alkyl", by any of the hydroxyl groups or R 10, is substituted hydrogen atoms bonded to carbon atoms
  • R 10 substituted hydrogen atoms bonded to carbon atoms
  • 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 meaning consisting of d to e carbon atoms, in which hydrogen atoms bonded to carbon atoms are optionally substituted by hydroxyl groups, is selected within the range of the designated number of carbon atoms. .
  • (C a -C b ) alkynyl optionally substituted with R 6 refers to the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R 6 from a to b
  • the alkynyl group, as defined above, is selected within each specified number of carbon atoms.
  • R 10 (C a ⁇ C b ) alkyl by any R 10, carbon atoms in which the hydrogen atoms bonded to carbon atom is optionally substituted from a ⁇ b Pieces
  • the above-mentioned meaning is an alkyl group, and each is selected within the range of the designated number of carbon atoms.
  • the oxime substituted amide compound represented by the formula (I) used as the active ingredient A of the present invention is a known compound described in International Publication (WO2014 / 010737), and specific examples thereof include the compounds in Table 1. It is done. However, the compounds in Table 1 are for illustrative purposes, and the oxime substituted amide compounds used as the active ingredient A of the present invention are not limited to these.
  • n-Pr and Pr-n represents a normal propyl group
  • i-Pr and Pr-i represents an isopropyl group
  • C-Pr and Pr-c are cyclopropyl groups
  • n-Bu and Bu-n are normal butyl groups
  • s-Bu and Bu-s are secondary butyl groups
  • the description of t-Bu and Bu-t represents a tertiary butyl group
  • the description of Pen-c represents a cyclopentyl group
  • Ph represents a phenyl group.
  • the notation “-” in the column of substituent Y 5 indicates that there is no corresponding substituent.
  • the notation of (R) and (S) in the column of substituent R 2 indicates that the (R) -form and (S) -form are 90% or more in the mixing ratio of the optical isomer of the carbon atom to which R 2 is bonded.
  • oxime-substituted amide compounds represented by the formula (I) used as the active ingredient A of the present invention are known compounds described in International Publication (WO2014 / 010737), and other compounds include, for example, It can be produced by the following production method.
  • the compound of the present invention represented by the formula (Ia) can be obtained by a method according to a known method or a compound represented by the formula (II) or a salt thereof (for example, a salt such as hydrochloride, hydrobromide, etc.)
  • the compound represented by (III) can be produced by using a condensing agent in the absence of a solvent or in a solvent, using an additive if necessary, and in the presence of a base if necessary. Examples of the known methods include The Journal of Organic Chemistry, 2004, Vol. 69, p.54-61, Tetrahedron Letters, 1994. 35, p.5603-5606, Tetrahedron Letters, 1997, 38, p.4853-4856, Tetrahedron, 2001, 57, p. 1551-1558 and the like.
  • the reaction mixture after completion of the reaction is directly concentrated, or dissolved in an organic solvent, washed with water, concentrated in ice water, or subjected to usual post-treatment such as concentration after extraction with an organic solvent, and the desired oxime substitution.
  • An amide compound can be obtained.
  • it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
  • Reaction formula 1 (In the formula, A 3 , Y 1 , Y 2 , Y 3 , Y 4 , R 1 , R 2 and R 3 represent the same meaning as described above, and J 1 represents a chlorine atom, a bromine atom or an iodine atom.)
  • the compound represented by the formula (II) is represented by the formula (II-1) according to a known method, for example, the method described in Synthesis Example 10 and Reaction Scheme 8 of Japanese Unexamined Patent Publication No. 2016-011286.
  • the compound represented by the formula (II-2), which can be produced by reacting the compound with hexamethylenetetramine, can be produced by reacting with an acid catalyst.
  • the reaction mixture after completion of the reaction or the purified and isolated salt of the compound represented by the formula (II) It can also be isolated as a free amine by neutralization with a base such as sodium, potassium carbonate or sodium hydroxide.
  • Reaction formula 2 (Wherein A 1 , A 2 , X 1a and r represent the same meaning as described above, and J 2 and J 3 each independently represent a leaving group such as a chlorine atom, a bromine atom or a methanesulfonyloxy group. , R a represents C 1 -C 4 alkyl, allyl or benzyl)
  • the compound represented by the formula (III-2) is, for example, Journal of Agricultural and Food Chemistry, 2014, Vol. 62, p.4063-4071 According to the description, it can be produced by reacting the compound represented by formula (III-1) with the compound represented by formula (IV).
  • the compound represented by the formula (IV) is known and generally available as a commercial product. Others can also be produced according to general synthesis methods described in known literature.
  • the compound represented by the formula (III-3) is prepared by combining a compound represented by the formula (III-2) with a compound represented by the formula (III-2) according to a general synthesis method, for example, a method described in International Publication (WO2010 / 201003081). It can manufacture by making the compound represented by (V) react.
  • the compound represented by the formula (III-4) is a compound represented by the formula (III-3) according to a known method, for example, the method described in Example 3 of the international publication (WO2015 / 199006). And an oxidizing agent.
  • the compound represented by the formula (III) is represented by the formula (III-4) according to a general synthesis method, for example, the method described in Step B2 of US Patent Application Publication No. 2010/0234604. It can manufacture by hydrolyzing the compound made.
  • each of the production intermediates that are the raw material compounds of production method A can be obtained by performing a general post-treatment.
  • each production intermediate produced by these methods can be used as it is in the next step without isolation and purification.
  • the chemical shift value of proton nuclear magnetic resonance ( 1 H-NMR) used for the identification of the compound is 300 MHz (model: ECX300 or ECP300, manufactured by JEOL) using Me 4 Si (tetramethylsilane) as a reference material. ).
  • Symbols in proton nuclear magnetic resonance chemical shift values have the following meanings. s: singlet, d: doublet, t: triplet, q: quartet, dd: double doublet, sep: septette, m: multiplet, br: broad
  • Step 2 Production of methyl 2- (methylsulfonyl) nicotinate To a solution of 5.70 g of methyl 2- (methylthio) nicotinate in 30 ml of acetic acid, 0.50 g of sodium tungstate dihydrate was added and stirred with ice cooling.
  • Step 3 Production of 2- (methylsulfonyl) nicotinic acid
  • a solution of 3.45 g of methyl 2- (methylsulfonyl) nicotinate in 20 ml of tetrahydrofuran was added 0.65 g of 10 ml aqueous solution of sodium hydroxide at room temperature. And stirred for 14 hours.
  • 50 ml of 5 wt% hydrochloric acid was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate (100 ml ⁇ 1).
  • Step 4 Preparation of 2-bromo-1- (3,5-dichloropyridin-2-yl) ethanone-O- (2,2,2-trifluoroethyl) oxime 2-bromo-1- (3,5- To a 110 ml toluene solution of 24.47 g dichloropyridin-2-yl) ethanone was added 42.54 g trifluoroacetic acid at room temperature and heated to 60 ° C. To the reaction solution was added dropwise a solution of 20.72 g of N- (2,2,2-trifluoroethoxy) carbamic acid-tert-butyl in 30 ml of toluene over 1 hour.
  • Step 5 Preparation of 2-amino-1- (3,5-dichloropyridin-2-yl) ethanone-O- (2,2,2-trifluoroethyl) oxime 12.90 g of hexamethylenetetramine 350 ml of ethyl acetate The suspension was heated and stirred at 50 ° C., and 2-bromo-1- (3,5-dichloropyridin-2-yl) ethanone-O- (2,2,2-trifluoroethyl) oxime 32.09 g of acetic acid Ethyl 180 ml solution was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at 50 ° C. for 4 hours.
  • reaction mixture was cooled to room temperature, and the precipitated solid was filtered and washed with 110 ml of ethyl acetate.
  • the obtained solid was suspended in 160 ml of methanol, and 100 g of 13 wt% hydrochloric acid was added. After the addition was complete, the reaction mixture was stirred at 50 ° C. for 1 hour. After completion of the reaction, the reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. A 10% by weight aqueous potassium carbonate solution was added to the resulting residue, and the mixture was extracted with a mixed solution of 30 ml of ethyl acetate and 150 ml of toluene.
  • Step 7 (Z) -N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (methylsulfonyl) nicotinic acid
  • amide N- [2- (3,5-dichloropyridin-2-yl) -2- (2,2,2-trifluoroethoxyimino) ethyl] -2- (methylsulfonyl) obtained in Step 6 Nicotinamide 325mg ethanol 4ml solution in a quartz cell (Tokyo Glass Instrument Co., Ltd., fully transparent for spectroscopic analysis), 100W high pressure mercury lamp (USHIO, lamp UM-102, lighting device UM-103B-B) ) For 20 hours.
  • Et represents an ethyl group
  • i-Pr represents an isopropyl group
  • Pr-c represents a cyclopropyl group
  • n-Bu represents a normal butyl group
  • s-Bu represents a sec-butyl group
  • Bu-c Represents a cyclobutyl group
  • Ph represents a phenyl group.
  • the notation of (S) in the column of substituent R 2 represents that the (S) -isomer is 90% or more in the mixing ratio of the optical isomer of the carbon atom to which R 2 is bonded, notation (RS) in the column of the substituents R 2, the compound represents that it is a racemate, the description of the (Z) in the column of the substituents R 1, the oxime geometric isomers substituent R 1 is attached In the mixing ratio, (Z) -form is 90% or more.
  • T-1, T-2, T-3, and E-4 each represent the following structure.
  • D-3-1b, D-3-2b, D-4-1b, D-4-2b, D-4-3b, D-5-3b, D-6-1a, D-7-1b , D-8-2b, D-9-1b, and D-10-1b each represent the following structure.
  • the notation [CH 2 (D-7-1b) -5-CF 3 ] represents a 5-[(trifluoromethyl) thiophen-2-yl] methyl group.
  • the description “* 1” in the melting point column means that the property of the compound was oily or resinous.
  • G 1 -1a, G 1 -1b , G 1 -2a, G 1 -2b, G 1 -2c, G 1 -2d, G 1 -2e, G 1 -2f, G 1 -2g, G 1 -2h represents G 1 -2i, G 1 -2j, G 1 -2k, the G 1 -2m, G 1 -2n and G 1 -2p respectively the following structures.
  • bactericidal, bactericidal, insecticidal or acaricidal active compound used as the active ingredient B (also referred to as active compound B) of the present invention include, for example, the groups BI to BX described in Tables 4 to 27, and CI A compound selected from the group of -C-XIV can be mentioned. That is, bactericidal and bactericidal active ingredient BI group; nucleic acid synthesis inhibitor
  • Examples of the compound having bactericidal, bactericidal, insecticidal or acaricidal activity used as the active ingredient B of the composition of the present invention include compounds selected from the following groups.
  • the suitable mixing ratio of the active ingredient A and the active ingredient B in the composition of the present invention and the method of the present invention is usually 0.001 to 1000 parts by weight, preferably 1 to 1000 parts by weight of the active ingredient B relative to 1 part by weight of the active ingredient A.
  • the amount is 0.01 to 100 parts by weight, more preferably 0.1 to 50 parts by weight, still more preferably 0.1 to 10 parts by weight.
  • the preferred treatment amount of the active ingredient compound in the composition of the present invention and the method of the present invention depends on the type of target disease to be controlled, but the active ingredient A is usually 0.1 to 10,000 ga. i. / Ha, preferably 0.1 to 2000 ga. i. / Ha, more preferably 0.1 to 1000 ga. i. / Ha, more preferably 1 to 300 ga. i. / Ha and the active ingredient B is 0.1 to 100,000 ga. i. / Ha, preferably 0.1 to 20000 ga. i. / Ha, more preferably 0.1 to 1000 ga. i. / Ha, more preferably 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. What is necessary is just to apply and apply a normal method to the object plant to be used, the seed, or the cultivation carrier for sowing. For example, it can be used in application methods such as rice seedling box application, seed dressing application method, seed disinfection method, planting hole treatment, plant base treatment, crop treatment, soil mixing treatment and the like.
  • 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.
  • a seedling carrier such as a plant source
  • watering is performed and the plant is absorbed and used.
  • hydroponics you may process to a hydroponic solution.
  • 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.
  • 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 the case of carrying out the method of the present invention indicates a support for cultivating a plant
  • the material is not particularly limited, but may be any material that can grow a plant.
  • 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 place where a plant is installed, a nursery for raising seedlings, before sowing or before planting a plant.
  • a method of spraying powder, wettable powder, granule wettable powder, granule, etc. to the planting holes, crops and the like can be mentioned.
  • 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.
  • a cultivation carrier in the vicinity of the plant being cultivated in addition to direct treatment on seeds, treatment on a cultivation carrier in the vicinity of the plant being cultivated is suitable.
  • 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.
  • the irrigation treatment of the liquid medicine or the granule spraying treatment to the nursery seedling bed can be performed.
  • a granule can also be processed to a planting hole at the time of planting, and can be mixed with the cultivation support
  • plant parasitic nematode control agent means a nematicide intended for controlling harmful nematodes that infect plants.
  • Plant in this specification refers to cereals and fruit trees / vegetables cultivated as human food, feed crops such as livestock and poultry, appreciation plants that love their form and shape, or planting in parks, streets, etc. It means a vascular plant (Tracheophyta), and 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) and the like magnolias (magnoliids), Konjac (Amorphophallus konjac), taro Edhod (Colocasia esculenta) and other taros (Araceae), Chinese yam (Dioscorea japonica) porrum), Onion Onion (Allium cepa), Rakkyo Rakkyo (Allium chinense), Green Onion Welsh onion (Allium fistulosum), Garlic Garlic (Allium sativum), Chives Chives (Allium schoenoprasum)
  • Rosaceae Pear (Amygdalus persica), Apricot (Prunus armeniaca), Cherry (Prunus avium), Prune Prune (Prunus domestica), Almond Almond (Prunus dulcis), Ume (Prunus mume), Japanese plum Plum (Prunus salicina), Western cherry (Cerasus speciosa), Yoshino cherry (Cerasus x yedoensis'Somei-yoshino '), Rose family (Rosaceae) ), Watermelon Watermelon (Citrullus lanatus), yuugao Bottle gourd (Lagenaria siceraria var.
  • Vulgaris spinach Spinach (Spinacia oleracea) )
  • Ebenaceae Cha Tea ⁇ plant (Camellia sinensis), Theaceae, Kiwifruit (Actinidia deliciosa, A. chinensis), etc. ry (Vaccinium spp.), cranberry Cranberry (Vaccinium spp.) and other azaleas (Ericaceae), coffee tree Coffee plants (Coffea spp.) and other red departments (Rubiaceae), lemon balm Lemon balm (Melissa spp.), Basil Basil (Ocimum basilicum), Shiso Shiso (PerillaPerfrutescens var.
  • Aceraceae such as Italianaceparsley (Petroselinum neapolitanum), Apiaceae, Udo (Aralia cordata), Araliaceae such as Aralia elata, Artichoke (Cynara scolymus), Asteraceae (Carduoideae), chrysanthemum (Chicory (Cichorium intybus), lettuce (Lactuca sativa), etc. (Helianthus annuus), Fuuki Fuki (Petasites japonicus), Burdock (Arctium lappa), etc. belonging to Asteraceae, Asteraceae, etc. Eudicots (eudicots).
  • nematode and “plant parasitic nematode” mean a nematode that becomes a pathogen causing damage to a plant, and specific examples thereof include the following nematodes, Specific examples are not limited to these.
  • sweet potato root nematode Melloidogyne incognita
  • Java root-knot nematode Java root-knot nematode
  • arenaria root-knot nematode Meloidogyne vola
  • Etc Etc.
  • Cryptaceae (Pratylenchidae), Clover cyst nematode (Heterodera trifolii), wheat cyst nematode (Heterodera avenae), okabo cyst nematode (Heterodera elachista), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera rostoen (Globodera pallida), Heterodera schachtii, and other heterodera families (Heteroderidae); citrophilus) and the like.
  • useful insects in the present specification means insects that are useful for human life by using their products, or for improving the efficiency of agricultural work such as use for pollination of fruit trees and vegetables.
  • Japanese bee Japanese honeybee (Apis cerana japonica), Western bee Western honey bee (Apis mellifera), Bumblebee Bumblebee (Bombus consobrinus wittenburgi, B. diversus diversus, B. hypocrita terporis, B. hypocrita (Osmia cornifrons), silkworm Silkworm (Bombyx ⁇ mori), and the like, but specific examples of useful insects are not limited thereto.
  • natural enemy in the present specification means an organism that kills or suppresses the growth of a specific species of organism, particularly a specific species that harms agricultural crops, by predation or parasitism.
  • the following organisms are listed, but specific examples of natural enemies are not limited to these.
  • Braconidae Braconidae
  • pods Ara
  • Ara Aral
  • cotton wasp Aphelinus gossypii
  • cross-horned wasp Aphelinus maculatus
  • wasp Aphelinus varipes
  • bee Encarsia formosa
  • Ecusmoceruscer mundus etc.
  • Futamon lizard Green lacewing belonging to the family Chrysopidae such as Dichochrysa osa formosanus, Chrysoperla nipponensis; Green lacewing; Predatory mite belonging to the family Phytoseiidae such as Amblyseius swirskii and Phytoseiulus persimilis;
  • composition of the present invention is effective against many plant nematode damage that occurs in vascular plants (Tracheophyta) such as Pinaces, magnoliids, monocots, monocots (eudicots), etc. Can be controlled.
  • the nematodes are Nematoda, Tylenchida, Rhabditida, Dorylaimida, Monhysterida, Araeolaimida, Chromadorida, and Enoprus. (Enoplida), Monochida, Dorylaimida, etc., but the composition of the present invention is a phytopathogenic nematode belonging to the order of the genus Coleoptera, Nematoda, Nisehari nematode, and Dorylaimida. Excellent control effect at low concentration.
  • composition of the present invention comprises an active ingredient A selected from oxime-substituted amide compounds represented by the formula (I) and an active ingredient B selected from known bactericidal, bactericidal, insecticidal or acaricidal active compounds, and remains as it is.
  • a surfactant, penetrant, spreading agent, thickener, antifreeze agent, binder, anti-caking agent, disintegration Agent, antifoaming agent, preservative, anti-degradation agent, etc. and add liquid (soluble concentrate), emulsion (emulsifiable concentrate), wettable powder (wettable powder), water solvent (water soluble powder), granular wettable powder (water
  • solid carrier examples include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, nostirite, and allophane.
  • Natural minerals such as shirasu, kira, talc, bentonite, activated clay, acid clay, pumice, attapulgite, zeolite and diatomaceous earth, for example natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgous clay and calcined diatomaceous earth Baked products, such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate and potassium chloride, such as glucose, fructose Sucrose Sugars such as lactose, polysaccharides such as starch, powdered cellulose and dextrin, organic substances such as urea, urea derivatives, benzoic acid and benzoic acid salts, such as wood flour, cork powder, corn cobs, walnut shells and tobacco Plants such
  • liquid carriers examples include aromatic hydrocarbons such as xylene, alkyl (such as C 9 or C 10 ) benzene, phenyl xylyl ethane, and alkyl (such as C 1 or C 3 ) naphthalene, machine oil, normal paraffin, isoparaffin, and the like.
  • aromatic hydrocarbons such as xylene, alkyl (such as C 9 or C 10 ) benzene, phenyl xylyl ethane, and alkyl (such as C 1 or C 3 ) naphthalene, machine oil, normal paraffin, isoparaffin, and the like.
  • Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol and benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol Ethers such as ethyl monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether and propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone and ⁇ -butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialky
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol and alkyl
  • Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyls Succinate, naphthalenesulfonate, alkylnaphthalenesulfonate
  • the dosage of the composition of the present invention varies depending on the application scene, application timing, application method, cultivated crop, etc., but generally the active ingredient amount is about 0.005 to 50 kg per hectare (ha), preferably 0.01. -20 kg, more preferably 0.01-5 kg is suitable.
  • formulation examples of the preparation when using the composition of the present invention are shown.
  • the formulation examples of the present invention are not limited to these.
  • “part” means part by weight
  • “active ingredient compound” is a general term for active ingredient A and active ingredient B.
  • 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.
  • 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.
  • Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.
  • wettable powder Compound No. 1 10 parts Compound No. 1 A02 10 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Co., Ltd., and so on) Carplex # 80D 2 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd., the same applies below) The above is uniformly mixed and ground to obtain a wettable powder.
  • Emulsifiable concentrate Compound No. 3 3 parts Compound No. C03 2 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industries, the same applies below) The above is uniformly mixed to obtain an emulsion.
  • Granule wettable powder (water dispersible granule) Compound No. 28 75 parts Haitenol NE-15 5 parts Vanillex N 10 parts Carplex # 80D 10 parts After uniformly mixing and pulverizing the above, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry Granule wettable powder.
  • each of the above preparations excluding the granules and powder is diluted 1 to 20000 times with water, and the active ingredient is 0.005 per hectare (ha) without diluting the granules and powder with water. It is sprayed to ⁇ 50 kg, preferably 0.01 to 20 kg, more preferably 0.01 to 5 kg.
  • the compounds listed in Table 2 (active ingredient A) and the compounds listed in Tables 4 to 27 (active ingredient B) were prepared according to formulation examples (emulsions). Each of these drugs was diluted with water to a concentration of 100 ppm to prepare a test drug solution. 300 ⁇ l of the prepared chemical solution was sprayed per 30 g of test soil and mixed. After filling the test soil after chemical solution treatment into the cell tray, cucumber was sown quickly. 21 days after sowing, the degree of root disease was observed. The degree of disease onset was expressed as a disease index (0: not diseased to 10: enormous disease onset). The control value (observed value) was calculated from the following formula using the disease index of the treated group and the disease index of the non-treated group.
  • Control value (%) (1-Disease index of treated area / Disease index of untreated area) ⁇ 100
  • E Theoretical value (%) expected when mixing active ingredient A and active ingredient B
  • Test Example 2 Nematocidal test against sweet potato nematode
  • the test drug solution was prepared by adding distilled water to a solution obtained by adding 100 ⁇ l of dimethyl sulfoxide to 1 mg of the compound described in Table 2 to a concentration of 100 ppm. After dispensing 60 ⁇ l of 1% agar medium to a 96-well plate, 30 ⁇ l of sterile water (10 eggs / 3 ⁇ l) containing eggs of Meloidogyne incognita was added to each well. The drug solution was added at 10 ⁇ l per well and allowed to stand at 25 ° C. under dark conditions.
  • Nematicidal rate (%) [(number of untreated eggs in treated area + number of inactive larvae) / number of active larvae in untreated area] ⁇ 100
  • the following compounds showed a nematicidal rate (%) of 50% or more.
  • Test Example 3 Nematicidal test for soybean cyst nematode
  • a test chemical solution having a concentration of 100 ppm of the compounds described in Table 2 was prepared. After dispensing 60 ⁇ l of 1% agar medium to a 96-well plate, sterile water (10 eggs / 3 ⁇ l) containing soybean cyst nematode (Heterodera glycines) eggs was added in an amount of 30 ⁇ l per well. The drug solution was added at 10 ⁇ l per well and allowed to stand at 25 ° C. under dark conditions.
  • the number of unhatched eggs and the number of inactive larvae 4 days after the addition of the chemical solution were measured, and the nematicidal rate (%) with respect to the untreated group was calculated by the calculation formula described in Test Example 2. As a result, the following compounds showed a nematicidal rate (%) of 50% or more.
  • Test Example 4 Soil irrigation treatment test for sweet potato nematode A test chemical solution having a concentration of 100 ppm of the compounds listed in Table 2 was prepared in the same manner as in Test Example 2. The chemical solution was treated at 1 ml per strain on a cell tray planted spinach seedling (about 2 weeks after germination) filled with 10 g of soil per cell. One hour after the treatment, water containing 2 L larvae of Meloidogyne incognita (2 L larvae: 100 heads / 1 ml) was inoculated to the strain, 1 ml per cell. 21 days after treatment, the degree of root disease was observed. The severity of the disease was expressed as a disease index (0: not diseased to 3: severe disease). The control value (%) was calculated from the calculation formula described in Test Example 1 using the disease index of the treated group and the disease index of the non-treated group.
  • Compound No . 1, 2, 3, 4, 5, 6, 7, 8, 11, 13, 14, 15, 18, 23, 24, 26, 27, 31, 32, 33, 34, 35, 38, 39, 40, 41, 43, 44, 45, 46, 47, 51, 53, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 73, 74, 75, 76, 78, 81, 84, 85, 86, 87, 89, 97, 101, 102, 104, 106.
  • Test Example 5 Soil admixture treatment test for sweet potato nematode A test chemical solution having a concentration of 300 ppm was prepared from the compounds listed in Table 2 in accordance with Formulation Example (emulsion). Test eggs were prepared by mixing 6 eggs of Meloidogyne incognita per gram of soil. The chemical solution was treated at 300 ⁇ l per 30 g of test soil, and then the test soil was mixed. After the test soil after mixing was filled in a cell tray, cucumber was quickly sown. 21 days after sowing, the degree of root disease was observed. The degree of disease onset was expressed as a disease index (0: not diseased to 10: enormous disease onset).
  • the control value (%) was calculated from the calculation formula described in Test Example 1 using the disease index of the treated group and the disease index of the non-treated group. As a result, the following compounds showed a control value (%) of 50% or more.
  • the control value (%) was calculated from the calculation formula described in Test Example 1 using the disease index of the treated group and the disease index of the non-treated group. As a result, the following compounds showed a control value (%) of 50% or more.
  • Test Example 7 Soil admixture treatment test for Kitagususa nematode A test chemical solution having a concentration of 300 ppm was prepared from the compounds listed in Table 2 according to the formulation example (emulsion). 400 ⁇ l each of the chemical solution was treated to 40 g of soil contaminated with Pratylenchus penetrans, and then the test soil was mixed. After the test soil after mixing was filled in a cell tray, burdock was quickly sown. Thirty days after sowing, the degree of root disease was observed. The degree of disease onset was expressed as a disease index (0: not diseased to 5: severe disease).
  • the control value (%) was calculated from the calculation formula described in Test Example 1 using the disease index of the treated group and the disease index of the non-treated group. As a result, the following compounds showed a control value (%) of 50% or more.
  • Test Example 8 Nematode test against sweet potato nematode (Comparative test 1) After adding 100 ⁇ l of dimethyl sulfoxide to 1 mg of the compound of the present invention and 1 mg of the comparative compound, distilled water was added to prepare a test chemical solution having the following predetermined concentration. A test similar to Test Example 2 was performed using these chemical solutions. Table 43 shows the nematicidal ratio (%) of each compound at a predetermined concentration.
  • Test Example 9 Nematode test against soybean cyst nematode (Comparative test 2) After adding 100 ⁇ l of dimethyl sulfoxide to 1 mg of the compound of the present invention and 1 mg of the comparative compound, distilled water was added to prepare a test chemical solution having the following predetermined concentration. A test similar to Test Example 3 was performed using these chemical solutions. Table 44 shows the nematicidal ratio (%) of each compound at a predetermined concentration.
  • composition of the present invention and the method of the present invention exhibit excellent control effects against various nematodes.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une nouvelle composition d'agent de lutte contre les organismes nuisibles, destinée en particulier à un agent nématicide. Cette composition d'agent nématicide contient : une ou plusieurs substances actives A choisies parmi des composés amides substitués par oxime représentés par la formule (I) ou des N-oxydes de ceux-ci ou des sels de ceux-ci ; et une ou plusieurs substances actives B choisies parmi des composés ayant une activité germicide, bactéricide, insecticide ou acaricide. [Dans laquelle : G1 représente une structure représentée par G1-1 et G1-2 ; G2 représente une structure représentée par G2-1, G2-2, etc. ; W représente un atome d'oxygène, etc. ; X1 représente trifluorométhyle, etc. ; Y1 représente un atome d'halogène, etc. ; Y2 représente un atome d'hydrogène, etc. ; Y3 représente un atome d'halogène, un alcynyle en C2-C6, etc. ; Y4 et Y5 représentent chacun indépendamment un atome d'hydrogène, etc. ; R1 représente un alkyle en C1-C6, etc. ; R2 et R3 représentent chacun indépendamment un atome d'hydrogène, méthyle, etc. ; et R4 représente un atome d'hydrogène, etc.]
PCT/JP2017/013020 2016-03-29 2017-03-29 Composition nématicide et procédé de lutte contre les nématodes WO2017170743A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2016-066420 2016-03-29
JP2016066420 2016-03-29
JP2017012004A JP2019094264A (ja) 2016-03-29 2017-01-26 殺線虫組成物及び線虫の防除方法
JP2017-012004 2017-01-26

Publications (1)

Publication Number Publication Date
WO2017170743A1 true WO2017170743A1 (fr) 2017-10-05

Family

ID=59965696

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/013020 WO2017170743A1 (fr) 2016-03-29 2017-03-29 Composition nématicide et procédé de lutte contre les nématodes

Country Status (1)

Country Link
WO (1) WO2017170743A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115160219A (zh) * 2021-07-20 2022-10-11 江苏中旗科技股份有限公司 含吡啶酰胺类结构的化合物及其制备方法和应用、杀菌剂

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014010737A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composé amide substitué par oxime et agent de lutte contre les organismes nuisibles
WO2015119246A1 (fr) * 2014-02-07 2015-08-13 日産化学工業株式会社 Composition bactéricide ou de stérilisation et méthode de lutte contre les maladies
WO2015147199A1 (fr) * 2014-03-28 2015-10-01 日産化学工業株式会社 Composition nématicide et procédé de lutte contre les nématodes
JP2016011286A (ja) * 2014-01-15 2016-01-21 日産化学工業株式会社 オキシム置換アミド化合物及び有害生物防除剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014010737A1 (fr) * 2012-07-12 2014-01-16 日産化学工業株式会社 Composé amide substitué par oxime et agent de lutte contre les organismes nuisibles
JP2016011286A (ja) * 2014-01-15 2016-01-21 日産化学工業株式会社 オキシム置換アミド化合物及び有害生物防除剤
WO2015119246A1 (fr) * 2014-02-07 2015-08-13 日産化学工業株式会社 Composition bactéricide ou de stérilisation et méthode de lutte contre les maladies
WO2015147199A1 (fr) * 2014-03-28 2015-10-01 日産化学工業株式会社 Composition nématicide et procédé de lutte contre les nématodes
JP2017095354A (ja) * 2014-03-28 2017-06-01 日産化学工業株式会社 殺線虫組成物及び線虫の防除方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115160219A (zh) * 2021-07-20 2022-10-11 江苏中旗科技股份有限公司 含吡啶酰胺类结构的化合物及其制备方法和应用、杀菌剂

Similar Documents

Publication Publication Date Title
CA2953903C (fr) Composition insecticide, acaricide, nematocide, molluscicide, de sterilisation ou bactericide, et procede de lutte contre les insectes nuisibles
CN109068648B (zh) 杀菌或杀细菌组合物和病害的防除方法
CN101686679B (zh) 杀线虫剂组合物及其使用方法
CA2878247C (fr) Compose amide substitue par oxime et agent de lutte contre les organismes nuisibles
TWI304324B (en) Pestcide composition and uses thereof
WO2018052136A1 (fr) Composition d'agent de lutte contre des nuisibles et procédé de lutte contre des nuisibles
CA2937876A1 (fr) Compositions comprenant des composes d'amide substitues par oxime et agents fongicides ou bactericides pour controler les malades de plantes
BR112013016460A2 (pt) compostos amidínicos e seu uso para o controle de doenças de plantas
JP2014114246A (ja) 殺虫、殺ダニ、殺線虫、殺軟体動物、殺菌又は殺バクテリア組成物及び病害虫の防除方法
JPWO2015125824A1 (ja) アルキニルピリジン置換アミド化合物及び有害生物防除剤
CN109863150B (zh) 1h-吡咯并吡啶化合物或其n-氧化物或其盐类以及含有该化合物的农业园艺用杀虫剂及其使用方法
JP2014037382A (ja) 殺虫、殺ダニ、殺線虫、殺軟体動物、殺菌又は殺バクテリア剤組成物及び病害虫の防除方法
IL277412A (en) Phenoxyurea compounds and pesticides
WO2017213137A1 (fr) Nouveau composé et produit chimique agricole/horticole l'utilisant comme ingrédient actif
WO2015147199A1 (fr) Composition nématicide et procédé de lutte contre les nématodes
JP2018024660A (ja) アミド化合物及び有害生物防除剤
WO2017170743A1 (fr) Composition nématicide et procédé de lutte contre les nématodes
CN114401633B (zh) 有害生物防除方法、以及有害生物防除剂组合物和有害生物防除剂套装
JP2019094264A (ja) 殺線虫組成物及び線虫の防除方法
CN114008045A (zh) 以新的咪唑并吡啶-2-羧酰胺衍生物为有效成分的农业园艺用药剂
JP2015155401A (ja) 置換ヘテロ環化合物及び有害生物防除剤
JP2017001958A (ja) 有用生物防除剤組成物およびその使用方法
JP2015214536A (ja) Ｎ−アルケニル置換アミド化合物及び有害生物防除剤
JP2013241403A (ja) マロン酸アミド化合物および有害生物防除剤
JP2019196310A (ja) 殺虫、殺ダニ、殺線虫、殺軟体動物、殺菌又は殺バクテリア組成物及び病害虫の防除方法

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 17775277

Country of ref document: EP

Kind code of ref document: A1