WO2018117034A1 - Composé oxadiazole et procédé de lutte contre des maladies des plantes - Google Patents

Composé oxadiazole et procédé de lutte contre des maladies des plantes Download PDF

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WO2018117034A1
WO2018117034A1 PCT/JP2017/045355 JP2017045355W WO2018117034A1 WO 2018117034 A1 WO2018117034 A1 WO 2018117034A1 JP 2017045355 W JP2017045355 W JP 2017045355W WO 2018117034 A1 WO2018117034 A1 WO 2018117034A1
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group
optionally
substituents selected
substituents
ring
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PCT/JP2017/045355
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博人 玉島
将起 山本
貞幸 有森
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住友化学株式会社
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    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to an oxadiazole compound and a method for controlling plant diseases.
  • Patent Document 1 describes an oxadiazole compound for pharmaceutical use.
  • An object of the present invention is to provide an excellent control method for plant diseases.
  • the present inventor has found that the compound represented by the following formula (I) has an excellent control effect against plant diseases. That is, the present invention is as follows. [1] Formula (I) [Where, G is a thiophene ring, furan ring, pyrrole ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, oxadiazole ring, thiadiazole ring, pyrazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine Ring or benzene ring ⁇ the thiophene ring, the furan ring, the pyrrole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the isothiazole ring, the pyrazo
  • Group A a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylthio group optionally having one or more halogen atoms, one or more substituents selected from group C
  • Group B C1-C6 alkylthio group optionally having one or more halogen atoms, phenyl group optionally having one or more substituents selected from Group F, one or more substituents selected from Group F A group consisting of a 5-6-membered aromatic heterocyclic group, a halogen atom, a nitro group and a cyano group, which may have a group;
  • Group C Group consisting of halogen atom, nitro group and cyano group.
  • Group D a C1-C6 alkyl group optionally having one or more substituents selected from group C, a C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, C1-C6 alkoxy group which may have one or more halogen atoms, C3-C6 alkenyloxy group which may have one or more halogen atoms, C3 which may have one or more halogen atoms -C6 alkynyloxy group, C1-C6 alkylthio group optionally having one or more halogen atoms, C1-C6 alkylsulfonyloxy group optionally having one or more halogen atoms, halogen atom, cyano group, A group consisting of a nitro group, a hydroxy group and an amino group.
  • Group E (C1-C6 alkyl) carbonylamino group optionally having one or more substituents selected from group C, or one or more substituents selected from group C (C1-C6) C6 alkyl) aminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group optionally having one or more substituents selected from group C, having one or more substituents selected from group C A C1-C6 alkylsulfonylamino group, a C1-C6 alkylaminosulfonyl group optionally having one or more substituents selected from group C, and one or more substituents selected from group C.
  • Group F a group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a halogen atom and a cyano group.
  • G X represents thiophene ring, furan ring, pyrrole ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, oxadiazole ring, thiadiazole ring, pyrazole ring, pyridine ring, pyrazine ring, pyridazine ring, Pyrimidine ring or benzene ring ⁇ the thiophene ring, the furan ring, the pyrrole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the isothiazole ring, the pyrazole ring, the pyridine ring, the pyrazine
  • the ring, the pyridazine ring, the pyrimidine ring, and the benzene ring may have
  • the ring may have one or more substituents selected from group D X ),
  • R 3X is one or more substituents optionally may C1-C6 alkyl group which may have one or more substituents may C3-C6 alkenyl which may have a selected from the group A X selected from the group A X A group, a C3-C6 alkynyl group optionally having one or more substituents selected from group A X , a C1-C6 alkoxy group optionally having one or more halogen atoms, selected from group D X 1 or may C3-C6 have a substituent of the cycloalkyl group, one or more substituents phenyl group which may have a selected from the group D X, one or more substituents selected from the group D X A 6-membered aromatic heterocyclic group which may have a group or a hydrogen atom, Z X represents C3-C6 cycloalkyl group, phenyl group, 6-membered
  • Group A X C1-C6 alkoxy group optionally having one or more halogen atoms, C1-C6 alkylthio group optionally having one or more halogen atoms, one or more substitutions selected from Group C X optionally may be C3-C6 cycloalkyl group having a group, one or more substituents phenyl group which may have a selected from the group F X, have one or more substituents selected from the group F X A group consisting of a 5-6 membered aromatic heterocyclic group, a halogen atom, a nitro group and a cyano group, which may be Group B X: 1 or more halogen atoms optionally may C1-C6 alkylthio group which may have one or more substituents phenyl group which may have a selected from the group F X, 1 is selected from the group F X A group consisting of a 5-6 membered aromatic heterocyclic group, a halogen atom, one or
  • Group C X a halogen atom, the group consisting of a nitro group and a cyano group.
  • Group D X: 1 or more substituents optionally may C1-C6 alkyl group which may have one or more substituents may C3-C6 cycloalkyl which may have a selected from the group C X selected from the group C X
  • Group E X may have one or more substituents selected from group C X (C1-C6 alkyl) carbonylamino group, may have one or more substituents selected from group C X (C1-C6 alkyl) aminocarbonyl group, one or more may have a substituent di (C1-C6 alkyl) aminocarbonyl group, one or more substituents selected from the group C X selected from the group C X the a and may C1-C6 alkylsulfonylamino group, one or more may C1-C6 be substituted alkylaminosulfonyl group selected from the group C X, one or more selected from the group C X A group consisting of a di (C1-C6 alkyl) aminosulfonyl group, a hydroxy group and an amino group, which may have a substituent.
  • Group F X A group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a halogen atom and a cyano group.
  • Group G X C1-C6 alkoxy group optionally having one or more halogen atoms, C1-C6 alkylthio group optionally having one or more halogen atoms, one or more substitutions selected from Group C X optionally may be C3-C6 cycloalkyl group having a group, one or more substituents phenyl group which may have a selected from the group F X, have one or more substituents selected from the group F X A group consisting of a 5-membered aromatic heterocyclic group, a halogen atom, a nitro group, and a cyano group, which may be ] (Hereinafter referred to as the present compound).
  • G X is a benzene ring optionally having one or more substituents selected from the group consisting of a halogen atom and a C1-C6 alkyl group
  • L X is C a (O)
  • X X is a NR 3X or an oxygen atom
  • R 2X is C1-C6 alkyl group, or a combination of a hydrogen atom or halogen atom
  • L X is S (O) 2
  • X X is NR 3X
  • R 2X is a combination of a C1-C6 alkyl group or a halogen atom
  • R 1X is a C1-C6 alkyl group, a hydrogen atom or a halogen atom
  • R 3X may have one or more substituents selected from group A X, and may have one or more substituents selected from group A X, C3-C6 alkynyl group, one or
  • An optionally substituted C3-C6 cycloalkyl group, a phenyl group optionally having one or more substituents selected from group D X , and an optionally substituted one or more substituents selected from group D X 5 A 6-membered aromatic heterocyclic group or a hydrogen atom, or R 7X and R 8X together with the nitrogen atom to which they are bonded (the 3-6-membered heterocyclic ring is have one or more substituents selected from the group D X forms also may), The compound according to 2].
  • G X is a benzene ring optionally having one or more halogen atoms, m is 1, The combination of L X, X X and R 2X is, L X is C (O), X X is an oxygen atom, R 2X is a combination of hydrogen atoms, or L X is S (O) 2 , X X is NR 3X , R 2X Is a C1-C3 alkyl group, R 1X is a hydrogen atom, R 3X is a hydrogen atom, Z X is CR 4X R 5X R 6X or NR 7X R 8X ; G X on the Z X -L X -X X - ( CR 1X R 2X) m is attached at the para position relative to the oxadiazole ring, R 4X , R 5X and R 6X are the same or different and are a C1-C6 alkyl group or a hydrogen atom, R 7X and R
  • a pest control agent containing the compound according to [2], [3] or [4] (hereinafter referred to as the present invention control agent).
  • [8] One or more selected from the group consisting of bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients and plant growth regulating ingredients, and [2], [3] or [4] A composition containing a compound.
  • plant diseases can be controlled.
  • the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, isobutyl group, tert- A butyl group, a pentyl group, and a hexyl group are mentioned.
  • alkenyl group examples include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, Examples include 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group and 5-hexenyl group.
  • alkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples thereof include 2-butynyl group, 4-pentynyl group and 5-hexynyl group.
  • “5-6-membered aromatic heterocyclic group” means a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group
  • the 5-membered aromatic heterocyclic group means a pyrrolyl group, a furyl group, a thienyl group, A pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group. Or represents a pyrazinyl group.
  • 3-6-membered non-aromatic heterocyclic group means oxirane group, oxacyclobutane group, tetrahydrofuran group, pyran group, dihydropyran group, aziridine group, azacyclobutane group, pyrrolidine group, piperidine group, oxazoline group, Represents an isoxazoline group, a thiazoline group, or an isothiazoline group;
  • cycloalkyl group represents a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.
  • the “3-7 membered cycloalkylene group” represents any one of the structures shown below (ZAA1 to ZAA5) ( ⁇ represents a bonding position).
  • Examples of the “3-7 membered saturated heterocyclic group” include an oxirane ring, oxetane ring, oxolane ring, oxane ring, oxepane ring, thiirane ring, thietane ring, thiolane ring, thiane ring, thiepan ring, 1,3-dioxolane ring. 1,3-dioxane ring, 1,3-dithiolane ring, and 1,3-dithiane ring.
  • R 7 and R 8 together with the nitrogen atom to which they are attached form a 3-8 membered heterocycle
  • R 7X and R 8X are together with the nitrogen atom to which they are attached
  • the “8-membered heterocycle” in the “form 8-membered heterocycle” represents any of the structures shown in the following (ZC1 to ZC21) ( ⁇ represents the bonding position).
  • X and Z together with L to which they are attached form a 4-7 membered heterocycle” and “X X and Z X together with L X to which they are attached are 4-7 membered heterocycles.
  • the “4-7 membered heterocycle” in “form a ring” represents, for example, any one of the structures shown below (ZF1 to ZF22) (• represents a bonding position).
  • the compound of the present invention may have one or more stereoisomers.
  • Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • the present invention includes each stereoisomer and any ratio of stereoisomer mixtures.
  • the compound of the present invention is mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • Examples of the compound of the present invention include the following compounds.
  • G X is a benzene ring optionally having one or more fluorine atoms
  • L X is C (O)
  • X X is NR 3X or an oxygen atom
  • R 2X is a C1-C6 alkyl group, hydrogen atom or halogen atom A combination, or a combination in which L X is S (O) 2
  • X X is NR 3X
  • R 2X is a C1-C6 alkyl group or a halogen atom
  • R 1X is a C1-C6 alkyl group, a hydrogen atom or a halogen atom
  • R 3X may have one or more substituents selected from group A X, and may have one or more substituents selected from group A X, C3-C6 alkynyl group, one or more halogen atoms optionally may C1-C6 al
  • the 5-6 membered heterocycle may have one or more substituents selected from group D X ), Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring, R 4X, R 5X and R 6X are the same or different phases, one or more substituents optionally may C1-C6 alkyl group which may have a selected from the group consisting of the group A X and the group E X, from the group A X C3-C6 alkynyl group optionally having one or more substituents selected, C1-C6 alkoxy group optionally having one or more substituents selected from group B X , selected from group D X 1 or may C3-C6 have a substituent of the cycloalkyl group, one or more substituents phenyl group which may have a selected from the group D X, one or more
  • G X is a benzene ring
  • L X is S (O) 2
  • X X is NR 3X
  • R 2X is a C1-C6 alkyl group or a halogen atom
  • Z X is a C3-C6 cycloalkyl group
  • CR 4X R 5X R 6X or NR 7X R 8X which may have one or more substituents selected from group D X ;
  • G X is a benzene ring
  • L X is S (O) 2
  • X X is NR 3X
  • R 2X is a C1-C6 alkyl group or a halogen atom
  • R 3X is a C1-C6 alkyl group, a C3-C6 alkynyl group or a C3-C6 cycloalkyl group optionally having one or more halogen atoms
  • Z X is a C3-C6 cycloalkyl group, CR 4X R 5X R 6X or NR 7X R 8X
  • R 4X , R 5X and R 6X are the same or different and each is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a hydrogen atom or a halogen atom which may have one or more halogen atoms
  • a compound in which R 7X and R 8X are the same or different and are
  • G X is a benzene ring optionally having one or more fluorine atoms
  • L X is C (O)
  • X X is an oxygen atom
  • R 1X and R 2X are the same or different and are a C1-C6 alkyl group, a hydrogen atom or a halogen atom
  • m is 1
  • Z X is NR 7X R 8X
  • Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the meta or para position with respect to the oxadiazole ring
  • R 7X and R 8X are the same or different and are a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of group A X and group E X , 1 selected from group A X A C3-C6 alkynyl group optionally having one or more substituents, a C1-C6 alkoxy
  • G X is a benzene ring
  • R 1X and R 2X are hydrogen atoms
  • a compound in which Z X -L X -X X- (CR 1X R 2X ) m is bonded to the para position relative to the oxadiazole ring on G X.
  • R 1X is a hydrogen atom
  • R 2X is a hydrogen atom or a methyl group
  • R 7X and R 8X are the same or different and each may have one or more substituents selected from the group consisting of group A X and group E X, a C1-C6 alkyl group, a C3-C6 alkenyl group, C3 -C6 alkynyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, phenyl group or a hydrogen atom, or R 7X and R 8X together with the nitrogen atom to which they are attached
  • a compound that forms a membered heterocycle (the 5-6 membered heterocycle may have one or more substituents selected from group D X ).
  • G X is a benzene ring
  • R 1X and R 2X are hydrogen atoms
  • Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring
  • R 7X and R 8X are the same or different and each may have one or more substituents selected from the group consisting of group A X and group E X, a C1-C6 alkyl group, a C3-C6 alkenyl group, C3 -C6 alkynyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, phenyl group or a hydrogen atom, or R 7X and R 8X together with the nitrogen atom to which they are attached
  • a compound that forms a membered heterocycle (the 5-6 membered heterocycle may have one or more substituents selected from group D X ).
  • R 1X is a hydrogen atom
  • R 2X is a hydrogen atom or a methyl group
  • R 7X and R 8X are the same or different and each may have one or more substituents selected from the group consisting of a C1-C3 alkoxy group and a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group Or a compound which is a hydrogen atom.
  • G X is a benzene ring
  • R 1X and R 2X are hydrogen atoms
  • Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring
  • R 7X and R 8X are the same or different and each may have one or more substituents selected from the group consisting of a C1-C3 alkoxy group and a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group Or a compound which is a hydrogen atom.
  • G X is a benzene ring optionally having one or more fluorine atoms
  • L X is C (O)
  • X X is NR 3X
  • R 1X and R 2X are the same or different and are a C1-C6 alkyl group, a hydrogen atom or a halogen atom
  • m is 1 or 2 Yes
  • R 3X may have one or more substituents selected from group A X, and may have one or more substituents selected from group A X, C3-C6 alkynyl group
  • one or more halogen atoms optionally may C1-C6 alkoxy group which may have one or more substituents have may be C3-C6 cycloalkyl group selected from the group D X, selected from the group D X is one or more substituents phenyl group which may have a one or more 6-membered aromatic or substituted heterocyclic group or a hydrogen atom selected from the group D
  • R 9X is 1 or more substituents optionally may C1-C3 alkyl group which may have a selected from the group consisting of the group E X and the group G X, have one or more substituents selected from the group A X
  • G X is a benzene ring, A compound in which R 1X and R 2X are a hydrogen atom and m is 1.
  • R 1X is a hydrogen atom
  • R 2X is a hydrogen atom or a methyl group
  • R 3X is 1 or more substituents optionally may C1-C6 alkyl group which may have a selected from the group A X, C3-C6 alkynyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, a phenyl group or A hydrogen atom
  • R 4X , R 5X and R 6X are the same or different and each may have one or more substituents selected from the group consisting of group A X and group E X, C1-C6 alkenyl group, C3-C6 alkenyl A group, a C3-C6 alkynyl group, a C1-C6 alkoxy group,
  • G X is a benzene ring
  • R 1X and R 2X are hydrogen atoms
  • m is 1
  • R 3X is 1 or more substituents optionally may C1-C6 alkyl group which may have a selected from the group A X, C3-C6 alkynyl group, C1-C6 alkoxy group, C3-C6 cycloalkyl group, a phenyl group or A hydrogen atom
  • Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring
  • R 4X , R 5X and R 6X are the same or different and each may have one or more substituents selected from the group consisting of group A X and group E X, C1-C6 alkenyl group, C3-C6 alkenyl A group, a C3-C6 alkynyl group, a C
  • R 1X is a hydrogen atom
  • R 2X is a hydrogen atom or a methyl group
  • m is 1
  • R 3X is 1 or more substituents optionally C1-C6 may be alkyl groups having a selected from the group A X, a phenyl group or a hydrogen atom
  • Z X is CR 4X R 5X R 6X or OR 9X
  • X X and Z X are taken together with L X to which they are attached to form a 5-6 membered heterocycle (the 5-6 membered heterocycle forms may) have one or more substituents selected from the group D X, Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring
  • R 4X , R 5X and R 6X are the same or different and are a C1-C6 alkyl group, a C3-C6 cycl
  • G X is a benzene ring
  • R 1X and R 2X are hydrogen atoms
  • m is 1
  • R 3X is 1 or more substituents optionally C1-C6 may be alkyl groups having a selected from the group A X, a phenyl group or a hydrogen atom
  • Z X is CR 4X R 5X R 6X or OR 9X , or X X and Z X together with L X to which they are attached form a pyrrolidinone ring or piperidinone ring
  • Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded to the para position with respect to the oxadiazole ring
  • R 4X , R 5X and R 6X are the same or different and are a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a phenyl group, a hydrogen atom or
  • G X is a benzene ring optionally having one or more fluorine atoms
  • L X is C (O)
  • X X is NR 3X or an oxygen atom
  • R 1X is a hydrogen atom
  • R 2X is a hydrogen atom or a methyl group
  • m is 1
  • R 3X is 1 or more substituents optionally C1-C6 may be alkyl groups having a selected from the group A X, a phenyl group or a hydrogen atom
  • Z X is CR 4X R 5X R 6X , NR 7X R 8X or OR 9X , or X X and Z X together with L X to which they are attached are 5-6 membered heterocycles
  • the 5-6 membered heterocyclic ring may have one or more substituents selected from group D X ), Z X -L X -X X- (CR 1X R 2X ) m on G X is bonded
  • G X is a benzene ring
  • R 2X is a hydrogen atom
  • R 3X is a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, or a hydrogen atom
  • Z X is CR 4X R 5X R 6X , NR 7X R 8X, or OR 9X , or X X and Z X together with L X to which they are attached, a pyrrolidinone ring or piperidinone ring
  • R 9X is a C1-C3 alkyl group or a phenyl group.
  • This compound can be produced by the following production method and the like.
  • This compound can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with trifluoroacetic anhydride in the presence of a base. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons such as hexane, cyclohexane, toluene and xylene (hereinafter referred to as hydrocarbons), diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert- Ethers such as butyl ether and diisopropyl ether (hereinafter referred to as ethers), halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene (hereinafter referred to as halogenated hydrocarbons), dimethylformamide (hereinafter referred to as DMF).
  • hydrocarbons such as hexane, cyclohexane, toluene and xylene
  • diethyl ether diethyl ether
  • tetrahydrofuran 1,4-dioxane
  • 1,4-dioxane 1,4
  • amides 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone
  • esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters), acetonitrile , Propionitrile, etc.
  • Lil hereinafter, referred to as nitriles.
  • Water and mixtures thereof.
  • Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, 2,2′-bipyridine, diazabicycloundecene (hereinafter referred to as organic bases), carbonates such as sodium carbonate and potassium carbonate ( Hereinafter, it is referred to as carbonates.), And bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as bicarbonates).
  • organic bases such as triethylamine, pyridine, 2,2′-bipyridine, diazabicycloundecene
  • carbonates such as sodium carbonate and potassium carbonate
  • bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as bicarbonates).
  • trifluoroacetic anhydride is usually used in a proportion of 1 to 10 mol
  • base is usually used in a proportion of 1 to 10 mol, relative to 1 mol of compound (A1).
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C
  • a compound represented by formula (2A2) (hereinafter referred to as compound (2A2)) is a compound represented by formula (2A1) (hereinafter referred to as compound (2A1)) and a compound represented by formula (M1) ( Hereinafter, it can be produced by reacting the compound (M1)) in the presence of a base.
  • X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, methanol and ethanol and other alcohols (hereinafter referred to as alcohols), water, and these. A mixture etc. are mentioned.
  • Examples of the base used in the reaction include organic bases, carbonates, hydrogen carbonates, and metal hydrides such as sodium hydride, potassium hydride, and lithium hydride (hereinafter referred to as metal hydrides). It is done.
  • compound (M1) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (2A1).
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (2A2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • the compound (M1) is known or can be produced according to a known method.
  • a compound represented by formula (2A3) (hereinafter referred to as compound (2A3)) is a compound represented by formula (A3) (hereinafter referred to as compound (A3)) and a compound represented by formula (M3) ( Hereinafter, it can be produced by reacting the compound (M3) in the presence of a base.
  • Z 1 represents NR 7 R 8 or OR 9 , and other symbols have the same meaning as described above.
  • the reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures thereof.
  • the compound (M3) may be in the form of an acid addition salt.
  • the acid addition salt of compound (M3) include hydrochloride and sulfate.
  • the base used in the reaction include organic bases, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides), carbonates, and bicarbonates. It is done.
  • compound (M3) is usually used at a ratio of 1 to 10 mol, and base is used at a ratio of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (2A3) can be isolated by performing post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M3) is publicly known or can be produced according to a publicly known method.
  • a compound represented by formula (2A4) (hereinafter referred to as compound (2A4)) is a compound represented by formula (A3-2) (hereinafter referred to as compound (A3-2)) and formula (M4). It can be produced by reacting the compound shown below (hereinafter referred to as compound (M4)) in the presence of a base or a Lewis acid. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures thereof. Examples of the base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • Lewis acid used in the reaction examples include aluminum (III) oxide.
  • compound (M4) is usually used in a proportion of 1 to 10 mol and base or Lewis acid is used in a proportion of 1 to 10 mol per 1 mol of compound (A3-2).
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (2A4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • Compound (M4) is publicly known or can be produced according to a publicly known method.
  • Reference manufacturing method A Compound (A1) can be produced by reacting a compound represented by formula (A2) with hydroxylamine. [Wherein the symbols have the same meaning as described above. ] The reaction can be carried out, for example, according to the method described in WO2009 / 081891.
  • the compound represented by the formula (A2-2) is a compound represented by the formula (A2-3) (hereinafter referred to as the compound (A2-3)) and a compound represented by the formula (M2) (hereinafter referred to as the compound (M2 And) in the presence of a base.
  • A2-3) a compound represented by the formula (A2-3)
  • M2 a compound represented by the formula (M2)
  • the reaction can be carried out according to the method described in International Publication No. 2015/004282.
  • Compound (A2-3) is known or can be produced according to the method described in International Publication No. 2011/142356.
  • Compound (M2) is known or can be produced according to a known method.
  • Reference manufacturing method C Compound (A3) can be produced by reacting compound (A3-2) with phosgene, diphosgene, or triphosgene in the presence of a base.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures thereof.
  • the base used in the reaction include organic bases, alkali metal hydroxides, carbonates, and hydrogen carbonates.
  • phosgene is usually used at a ratio of 1 to 10 mol, and base is used at a ratio of 1 to 10 mol.
  • diphosgene is usually used at a ratio of 0.5 to 5 mol, and the base is used at a ratio of 1 to 10 mol.
  • triphosgene is usually used in a proportion of 0.3 to 3 mol, and the base is used in a proportion of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (A3) can be obtained by concentrating the reaction mixture. Moreover, you may use for the method as described in the manufacturing method C, without concentrating a reaction mixture.
  • the compound (A3-2) is produced by reacting a compound represented by the formula (A3-3) (hereinafter referred to as the compound (A3-3)) and an acid in the presence of water or alcohols.
  • A3-3 a compound represented by the formula (A3-3)
  • the reaction is usually carried out using water and / or alcohols as a solvent, but a solvent may be further added.
  • solvents include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures thereof.
  • the acid used in the reaction include hydrochloric acid, sulfuric acid, and paratoluenesulfonic acid.
  • the acid is usually used at a ratio of 1 to 1000 mol per 1 mol of the compound (A3-3).
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (A3-2) can be isolated by performing post-treatment operations such as mixing of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • Reference manufacturing method E Compound (A3-3) is produced by reacting a compound represented by formula (A1-2) (hereinafter referred to as Compound (A1-2)) with trifluoroacetic anhydride in the presence of a base.
  • A1-2 a compound represented by formula (A1-2)
  • trifluoroacetic anhydride in the presence of a base.
  • Reference manufacturing method F Compound (A1-2) can be produced by reacting a compound represented by formula (A2-4) (hereinafter referred to as compound (A2-4)) with hydroxylamine. [Wherein the symbols have the same meaning as described above. ] The reaction can be carried out, for example, according to the method described in WO2009 / 081891.
  • Compound (A2-4) can be produced by reacting a compound represented by the formula (A2-5) (hereinafter referred to as compound (A2-5)) with chloromethyl methyl ether. [Wherein the symbols have the same meaning as described above. ] The reaction is described in, for example, J. Am. Chem. Soc. , 1977, 99, 1275.
  • Compound (A2-5) is publicly known or can be produced according to the method described in US Patent Application Publication No. 2007/270438.
  • the compound represented by formula (A2-6) is a compound represented by formula (A4-1) (hereinafter referred to as compound (A4-1)) and a compound represented by formula (M5) (hereinafter referred to as compound (M5 And) in the presence of a base.
  • A4-1) a compound represented by formula (A4-1)
  • M5 a compound represented by formula (M5 And) in the presence of a base.
  • the reaction can be carried out according to the method described in Angew. Chem. Int. Ed., 2016, 55, 8452.
  • Compound (A4-1) is publicly known or can be produced according to the method described in International Publication No. 2011/142356.
  • Compound (M5) is publicly known or can be produced according to a publicly known method.
  • This compound is usually mixed with a solid carrier, liquid carrier, oil, and / or surfactant, etc., and if necessary, an adjuvant for formulation such as a sticking agent, a dispersing agent, a stabilizer and the like, It is formulated into granular wettable powder, flowable powder, granule, dry flowable liquid, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like. These preparations contain the present compound in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
  • the control agent of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier, liquid carrier, oil, and / or surfactant, and if necessary, an auxiliary agent for formulation such as a fixing agent, a dispersant, a stabilizer and the like.
  • an auxiliary agent for formulation such as a fixing agent, a dispersant, a stabilizer and the like.
  • preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
  • These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
  • solid support examples include clays (for example, kaolin, diatomaceous earth, scissors clay, bentonite, acidic clay), dry silica, wet silica, talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate) and the like.
  • clays for example, kaolin, diatomaceous earth, scissors clay, bentonite, acidic clay
  • dry silica wet silica
  • talc and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate) and the like.
  • liquid carrier examples include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons ( Examples thereof include n-hexane, kerosene), esters, nitriles, ethers, amides, and halogenated hydrocarbons.
  • ketones eg, acetone, methyl ethyl ketone, cyclohexanone
  • aromatic hydrocarbons eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene
  • aliphatic hydrocarbons examples thereof include n-hexane, kerosene
  • esters nitriles, ethers, amides, and halogenated hydrocarbons.
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Is mentioned.
  • formulation adjuvants include, for example, a fixing agent, a dispersant, and a stabilizer.
  • a fixing agent for example, a fixing agent, a dispersant, and a stabilizer.
  • casein gelatin, polysaccharides (for example, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, Saccharides, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4 -Mixtures of -methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
  • the present compound may be used for controlling plant diseases by mixing with mineral oil, oil such as vegetable oil, or surfactant.
  • the compound of the present invention may be used for controlling pests by mixing with oils such as mineral oil and vegetable oil, or surfactants.
  • Oils that can be used in combination, or surfactants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru ( (Registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (Registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGLAR 90 (registered trademark), AGROTIN
  • the method is not particularly limited as long as the present compound can be applied.
  • seed treatment such as seed disinfection.
  • the method of applying the compound of the present invention is not particularly limited as long as the compound of the present invention can be applied.
  • the application amount of the present compound or the present compound varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc. In the case of the treatment, the amount is usually 1 to 500 g, preferably 2 to 200 g per 1000 m 2 . In the case of treating seeds, the amount of the present compound or the compound of the present invention is usually applied in the range of 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg of seeds. Emulsions, wettable powders, suspensions and the like are usually diluted with water before use. In this case, the concentration of the present compound or the present compound after dilution is usually 0.0005 to 2% by weight, preferably 0. 0.005 to 2% by weight. Powders, granules and the like are usually applied as they are without dilution.
  • the present compound or the present compound can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards.
  • This compound or this invention compound can control the disease of the said agricultural land in the agricultural land etc. which grow the plant etc. which are mentioned below.
  • this invention compound can control the harmful arthropod of the said agricultural field.
  • Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc. Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, coral rabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables ( Burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery vegetables (carrots, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.), perilla Vegetables (Perilla, Mint, Basil) Etc.), strawberry, sweet potato, yam, taro, etc., flower bud, houseplant, Fruit trees; pears (apples, pears, Japanese pears, quince, quince
  • Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
  • the above plants include genetically modified crops.
  • Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Erysiphe) graminis), red mold (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P.
  • plague (Phytophthora parasitica, Phytophthora citrophthora); apple monilinia (Monilinia) mali), rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black star disease (Venturia inaequalis), anthracnose (Glomerella cingulata), brown spot disease (Diplocarpon mali) Botryosphaeria berengeriana, plague (Phytophtora cactorum); pear black spot (Venturia nashicola, V.
  • pirina black spot (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); Disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp.
  • Rice seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease.
  • Viral diseases of various crops mediated by Polymyxa genus or Olpidium genus.
  • Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citri); carotovora) etc.
  • Examples of harmful arthropods that can be controlled by the compounds of the present invention include the following. Hemiptera: Japanese brown planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted plant (Javesella pellucida), black-tailed squid (Delphacidae); Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Eki ca ), Corn Leaf Hopper (Dalbulus maidis), Cofana spectra, etc., Cicadellidae; Mahanarva posticata, Mahanarva fimbriolata, etc., Cercopidae; Aphis fabae, soybean aphids (Aphis glycines), cotton a
  • Leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae) and other aphids (Phylloxeridae); ; Scotinophara lurida, Malayan rice black bug (Scotinophara coarctata), Nezara antennata, Eysarcoris aeneus, Eysarcoris ysori village Eysarcoris annamita, Hailyomorpha halys, Southern stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalchel pugnax Pentatomidae); Burrower brown bug (Scaptocoris castanea) and other hornworms (Cydnidae); ); Coleus punctiger, Leptoglossus australis, etc.
  • Lepidoptera Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itteno eel moth (Scirpophaga incertulas), Rupela albina medina, Hacasino maiga (Marasmia exigua), cotton moth (Notarcha derogata), yellow corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), yellow moth (Hellula undalis), monk black moth terrel Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc.
  • Thysanoptera Citrus thrips (Frankliniella occidentalis), Thrips palmiet (Sriptos etbisiton) ), Thripidae such as Echinothrips americanus; Phthaothripripae such as Haplothrips aculeatus.
  • Diptera Drosophila (Delia platura), onion flies (Delia antiqua), etc., Anthomyiidae; Tomato leafhopper (Liriomyza sativae), bean leafworm (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafworms (Agromyzidae); ), Eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quinzland fruit fly (Bactrocera tryoni), CeratitisCcapitata, etc.
  • Coleoptera Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cue Diabrotica balteata), Cucurbit tle Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Bark beetle (Oulema melanopus), potato beetle (Aulacophora femoralis), Phyllotreta bb Cabe black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Inedro beetle (Oulema oryzae), Grape colaspi
  • Carabidae Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), Black marsh (Tomarus gibbosus), Holotrichiall Haga crinita) and other genus Phyllophaga genus (Phyllophaga spp.), Diloboderus usabderus genus Diloboderus genus (Diloboderus spp.) and other scarab beetles (Scarabaeidae); Eusces Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus S subsignatus), Sugarcane weevil (Sphenophorus levis), Sabihyo weevil (Scepticus griseus) mis), Brazilian weevil (Zabrotes subfasciat
  • Tribolium castaneum, Tribolium confusum, etc . Tribolium castaneum, Tribolium confusum, etc .; Tenebrionidae; Epilachna vigintioctopunctata, etc .; Bostrychidae; Leopardidae (Ptinidae); Anoplophora malasiaca, Migdolus fryanus, etc. , Melanotus legatus, Anchastus spp., Connoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., Etc. Elateridae; Staphylinidae such as Paederus fuscipes.
  • Orthoptera Tosama locust (Locusta migratoria),ixie flying grasshopper (Dociostaurus maroccanus), Australian flying grasshopper (Chortoicetes terminifera), Red-spotted grasshopper (Nomadacris septemfasciata), Brown Locust ina Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoula femurrubrum) gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Red-tailed hawk (Oxya japonica), Grasshopper Locust (Patanga succincta), etc. ridi
  • Hymenoptera bee (Athalia rosae), Japanese bee (Athalia japonica) and other bees (Tenthredinidae); Department (Formicidae) etc.
  • Cockroaches (Blattodea): German cockroaches (Blattellidae) such as the German cockroach (Blattella germanica); Family (Blattidae); Yamato termite (Reticulitermes speratus), Japanese termite (Coptotermes formosanus), American ant termite (Incisitermes orminor), Great white termite (Cryptotermes domesticus), Thai one termite (Odontotermes ⁇ ant hunter) (Glyptotermes satsumensis), Nakajima Termites (Glyptotermes nakajimai), Caterpillars (Glyptotermes fuscus), Termites (Hodotermopsis sjostedti), Coptotermes guangzhouen sis), Amite Termites (Reticulitermes amamianus), Miyatake Termites (Reticulitermes miyatakei), Camellia Termites (Reticuli
  • the present compound 1 1 H-NMR (CDCl 3 ) ⁇ : 8.15-8.11 (2H, m), 7.53-7.50 (2H, m), 4.76-4.72 (1H, m), 4.59 (1H, d), 2.86 -2.79 (1H, m), 2.76-2.69 (1H, m), 1.59 (3H, d), 1.24 (3H, t).
  • the present invention compounds 7 (R 11: CH 3, R 12: c-Hex): 1 H-NMR (CDCl 3 ) ⁇ : 8.11 (2H, d), 7.51 (2H, d), 5.21 (2H, s), 4.07-3.82 (1H, m), 2.83 (3H, s), 1.90-1.02 (10H, m).
  • Production Example 4-2 The compounds produced according to the method described in Production Example 4-1, and their physical properties are shown below.
  • Production Example 6-2 The compounds produced according to the method described in Production Example 6-1 and their physical properties are shown below.
  • Production Example 6-3 The compounds produced according to the method described in Production Example 6-1 and their physical properties are shown below.
  • Compound 63 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.10 (2H, d), 7.98 (1H, s), 7.49 (2H, d), 6.68-6.95 (2H, m), 4.70 (2H, d ), 3.94 (3H, s)
  • Compound 64 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.17-8.18 (1H, m), 8.10 (2H, d), 7.61-7.63 (1H, m), 7.48 (2H, d), 6.58-6.61 (1H, m), 6.35-6.35 (3H, m), 4.67-4.69 (2H, m)
  • Reference production example 4-2 The compounds produced according to the method described in Reference Production Example 4-1 and their physical properties are shown below.
  • Reference production example 5-2 At room temperature, 3.6 mL of potassium tert-butoxide (1.0 M, tetrahydrofuran solution) was added to a mixture of 0.50 g of phenylurethane and 15 mL of tetrahydrofuran. To the mixture, 0.58 g of 4-cyanobenzyl bromide was added and stirred at room temperature for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • potassium tert-butoxide 1.0 M, tetrahydrofuran solution
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • i-Pr represents an isopropyl group
  • c-Pr represents a cyclopropyl group
  • Bu represents a butyl group.
  • I-Bu represents an isobutyl group
  • t-Bu represents a tert-butyl group
  • c-Bu represents a cyclobutyl group
  • Pen represents a pentyl group
  • c-Pen represents a cyclopentyl group
  • Hex represents hexyl C-Hex represents a cyclohexyl group
  • OCH 2 CH ⁇ CH 2 represents an allyloxy group
  • OCH 2 C ⁇ CH represents a propargyloxy group
  • Ph represents a phenyl group
  • Bn represents a benzyl group.
  • 2-Py represents a 2-pyridyl group
  • 3-Py represents a 3-pyridyl group
  • 4-Py represents a 4-pyridyl group
  • Pyr represents a 1-pyrrolidinyl group
  • Pip represents - represents a piperidyl group
  • Mor represents a morpholin-4-yl group.
  • the substituent number RA4 represents a combination in which R 21 , R 22 , R 24 and R 25 are hydrogen atoms, R 23 is a methyl group, and R 26 is an isopropyl group.
  • the present compound RA4 means a compound having a substituent number of RA4 in the compound represented by the formula (III), and R 21 , R 22 , R 24 and R in the compound represented by the formula (III).
  • 25 represents a hydrogen atom
  • R 23 represents a methyl group
  • R 26 represents an isopropyl group.
  • the substituent numbers ZA1 to ZA8289 are combinations of R 31 , R 32 , R 33 , R 34 and R 35 in the compound represented by the formula (IV) or the compound represented by the formula (V). In the following, it will be referred to as [substituent group number; R 31 , R 32 , R 33 , R 34 , R 35 ].
  • the substituent number ZA2 represents a combination in which R 31 , R 32 , R 33 and R 34 are hydrogen atoms and R 35 is NHEt.
  • the present compound RB2 means a compound having a substituent number ZA2 in the compound represented by the formula (IV), and R 31 , R 32 , R 33 and R in the compound represented by the formula (IV).
  • 34 represents a hydrogen atom
  • R 35 represents NHEt.
  • [ZA5751; H, F, H, H, O (CH 2 ) 2 OPr], [ZA5752; H, F, H, H, O (CH 2 ) 3 OPr], [ZA5753; H, F, H, H , OCH 2 CN], [ZA5754; H, F, H, H, O (CH 2 ) 2 CN], [ZA5755; H, F, H, H, O (CH 2 ) 3 CN], [ZA5756; H , F, H, H, O (CH 2 ) 4 CN], [ZA5757; H, F, H, H, O (CH 2 ) 5 CN], [ZA5758; H, F, H, H, OCH 2 CH CH 2 ], [ZA5759; H, F, H, H, OCH 2 C ⁇ CH], [ZA5760; H, F, H, H, OCH 2 C ⁇ CCH 3 ], [ZA5761; H, F, H , H, OCH 2 Ph], [ZA5762; H, F, H
  • the present compound RD2 means a compound having the substituent number ZA2 in the compound represented by the formula (V), and in the compound represented by the formula (V), R 31 , R 32 , R 33 and R 34 are It represents a compound represented by the following, which is a hydrogen atom and R 35 is NHEt.
  • R 41 , R 42 , R 43 , R 44 , R 45 , R 46 the substituent number RC4 represents a combination in which R 41 , R 42 , R 43 , R 44 and R 45 are hydrogen atoms and R 46 is an isopropyl group.
  • the present compound RC4 means a compound whose substituent number is RC4 in the compound represented by the formula (VI), and R 41 , R 42 , R 43 , R in the compound represented by the formula (VI). 44 and R 45 represent a hydrogen atom and R 46 represents an isopropyl group.
  • the present compound RA, the present compound RB, the present compound RC and the present compound RD are referred to as the present compound A.
  • the present compound or the present compound can be used in combination or in combination with a bactericidal active ingredient, an insecticidal active ingredient, an acaricidal active ingredient, a nematocidal active ingredient or a plant growth regulating ingredient (hereinafter collectively referred to as this ingredient).
  • a bactericidal active ingredient an insecticidal active ingredient, an acaricidal active ingredient, a nematocidal active ingredient or a plant growth regulating ingredient
  • this ingredient treating a plant or soil with one or more selected from the group consisting of bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients and plant growth regulating ingredients, and a composition containing the compound of the present invention It is possible to control pests such as harmful arthropods, harmful linear animals, and plant pathogens.
  • a bactericidal active ingredient is an ingredient used to protect plants from diseases caused by phytopathogenic fungi (filamentous fungi and bacteria). For example, it is prescribed by FRAC (Fungicide Resistance Action Committee) etc. Can be mentioned. Examples of the insecticidal active ingredient, acaricidal active ingredient and nematocidal active ingredient include those prescribed by, for example, IRAC (Insecticide Resistance Action Committee).
  • the plant growth regulating component means a component that regulates plant growth, such as fruiting promotion and rooting promotion, and examples thereof include indole butyric acid.
  • tebuconazole + SX means a combination of tebuconazole and SX.
  • the abbreviation SX means any one compound selected from Compound A.
  • the numbers in parentheses represent CAS registration numbers.
  • the ratio of the present compound or the present compound and the present component is not particularly limited, but is 1000: 1 to 1: 1000, 500: 500 by weight ratio (the present compound: the present component or the present compound: the present component).
  • Formulation Example 1 A formulation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the present compounds A, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of wet silica.
  • Formulation Example 2 After mixing 20 parts of any one of the present compounds A and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, To this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.
  • Formulation Example 3 A formulation is obtained by thoroughly crushing and mixing 2 parts of any one of the present compounds A, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the present compounds A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 After thoroughly mixing 2 parts of any one of the present compounds A, 1 part of wet silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, add water and knead well. The preparation is obtained by grain drying.
  • Formulation Example 6 A mixture of 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of any one of the present compounds A, and 45 parts of water is sufficiently mixed. Get.
  • Test Example 1 or Test Example 2 is a test conducted under the same conditions as described in each test example except that dimethyl sulfoxide was dispensed instead of the dimethyl sulfoxide diluting solution containing this compound. Represents a ward.
  • the term “no treatment” in Test Example 3 to Test Example 15 means that the foliage spraying of the water-diluted solution of the preparation containing the present compound was not performed.
  • Test Example 1 Control test against tomato leaf mold fungus (Cladosporium fulvum) Compound 2, 6, 8, 9, 11, 14, 19, 21, 26, 28, 33-37, 39, 46, 49, 51, 56 of the present invention , 63 or 64 is diluted with dimethyl sulfoxide so as to contain 1500 ppm, and 1 ⁇ L is dispensed into a titer plate (96-well), and then the tomato leaf blight fungus (cytochrome b encoding gene 129th of cytochrome b) 150 ⁇ L of a potato broth liquid medium (PDB medium) inoculated with spores of a QoI resistant strain whose nucleotide sequence was mutated so that the amino acid residue was substituted from phenylalanine to leucine was dispensed.
  • PDB medium potato broth liquid medium
  • This plate was cultured at 18 ° C. for 5 days to proliferate the tomato leaf mold, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of the tomato leaf mold.
  • Test Example 2 Control Test Against Wheat Leaf Blight Fungus (Septoria tritici) Compound 2, 4, 9, 12, 15-18, 22-27, 30, 33-40, 42, 46, 50, 56, 61, 63 of the present invention
  • PDB medium potato broth liquid medium
  • the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of wheat leaf blight fungi.
  • the growth degree in the section treated with the compound 2, 4, 9, 12, 15-18, 22-27, 30, 33-40, 42, 46, 50, 56, 61, 63 or 64 of the present invention is increased.
  • Test Example 3 Control Test for Soybean Rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown there, grown in a greenhouse for 10 days, and an aqueous suspension of soybean rust fungus spores. Was spray-inoculated. After inoculation, the present compound 1 was formulated according to the method described in Formulation Example 6 after placing soybeans in a humid room at 23 ° C. in the daytime and 20 ° C. for 1 day in a humid room and then cultivating in the greenhouse for 2 days.
  • soybean -7, 9-26, 28-46, 49-51, 53, 56-59, 61, 63, 64 or the present compound 1 is mixed with water to a concentration of 200 ppm, The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and then the lesion area was examined. As a result, there was no lesion area in soybeans treated with the present compounds 1-7, 9-26, 28-46, 49-51, 53, 56-59, 61, 63, 64 or the present compound 1. It was 30% or less of the lesion area in the treated soybean.
  • Test Example 4 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and soybean (cultivar; Kurosengoku) was sown therein and allowed to grow in a greenhouse for 13 days.
  • the present compounds 1-26, 28-44, 46-59, 61-64 or the present compound 1 formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 200 ppm, The mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the soybean. After spraying, the soybeans were air-dried, and after 4 days, sprayed with a water suspension of soybean rust spores. After inoculation, soybeans were placed in a humid room at 23 ° C.
  • the lesion area in the soybean treated with the present compounds 1-26, 28-44, 46-59, 61-64 or the present compound 1 was 30% or less of the lesion area in the untreated soybean. there were.
  • Test Example 5 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days.
  • the compound 1, 4, 5, 6, 37, 43 or 44 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 500 ppm, and the mixture is mixed with the above rice The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the rice is air-dried and left for 6 days in contact with a rice seedling (variety: Hinohikari) that has been treated with the rice blast fungus under a high humidity of 24 ° C in the daytime and 20 ° C in the nighttime.
  • the lesion area was investigated. As a result, the lesion area in the rice treated with the present compound 1, 4, 5, 6, 37, 43 or 44 was 30% or less of the lesion area in the untreated rice.
  • Test Example 6 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days. Thereafter, the present compound 2, 5, 14, 15, 19, 31, 34, 43, 44 or 46 formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm. The mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the rice. After spraying, the rice is air-dried and left for 6 days in contact with a rice seedling (variety: Hinohikari) that has been treated with the rice blast fungus under a high humidity of 24 ° C in the daytime and 20 ° C in the nighttime. The lesion area was investigated. As a result, the lesion area in the rice treated with the present compound 2, 5, 14, 15, 19, 31, 34, 43, 44 or 46 is 30% or less of the lesion area in the untreated rice. there were.
  • Test Example 7 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was sown therein and cultivated in a greenhouse for 10 days.
  • the present compound 1-7, 9-18, 22-24, 38, 43 or the present compound 1 formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 500 ppm, The mixture was sprayed on the foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried, and after 4 days, a water suspension containing spores of wheat leaf blight was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C.
  • the lesion area in the wheat treated with the present compounds 1-7, 9-18, 22-24, 38, 43 or the present compound 1 was 30% or less of the lesion area in the untreated wheat. there were.
  • Test Example 8 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was sown therein and cultivated in a greenhouse for 10 days. Compound 1, 2, 6, 9-20, 22-24, 26, 28-34, 38, 44, 46, 48, 50, 51, 53 of the present invention formulated according to the method described in Formulation Example 6 ⁇ 59, 63, or 64 was mixed with water to a concentration of 200 ppm, and the mixture was sprayed on the foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried, and after 4 days, a water suspension containing spores of wheat leaf blight was spray-inoculated.
  • the wheat was placed under high humidity at 18 ° C. for 3 days, then cultivated under illumination for 14 to 18 days, and then the lesion area was examined.
  • the lesion area was 30% or less of the lesion area in untreated wheat.
  • Test Example 9 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, seeded with wheat (variety; apoge), cultivated in a greenhouse for 10 days, and water suspension of wheat leaf blight fungus spores The solution was spray inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, and then the compound 9 of the present invention formulated according to the method described in Formulation Example 6 was mixed with water to a concentration of 200 ppm. The foliage was sprayed so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried and placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with Compound 9 of the present invention was 30% or less of the lesion area in the untreated wheat.
  • Test Example 10 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, seeded with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days. The present compound 1-7, 9-18, 22-25, 27-29, 37, 38, 40, 42-44 or the present compound 1 formulated according to the method described in Formulation Example 6 at a concentration of 500 ppm Then, the mixture was sprayed with foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried and cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus.
  • the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination.
  • the lesion areas in the wheat treated with the present compounds 1-7, 9-18, 22-25, 27-29, 37, 38, 40, 42-44 or the present compound 1 were all untreated. It was 30% or less of the lesion area in wheat.
  • Test Example 11 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, seeded with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days. Compounds of the present invention 1, 4, 6, 9 to 26, 28 to 31, 37, 38, 42 to 44, 46 to 48, 51 to 54, 56 to 59 formulated according to the method described in Formulation Example 6 61-64 or the present compound 1 was mixed with water to a concentration of 200 ppm, and the mixture was sprayed on the foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried and cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus.
  • the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination.
  • the present compound 1, 4, 6, 9 to 26, 28 to 31, 37, 38, 42 to 44, 46 to 48, 51 to 54, 56 to 59, 61 to 64 or the present compound 1 was treated.
  • the lesion area in wheat was 30% or less of the lesion area in untreated wheat.
  • Test Example 12 Control test against soybean powdery mildew (Microsphaera diffusa) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown, cultivated in a greenhouse for 10 days, and soybean affected with soybean powdery mildew The seedlings (variety: Kurosengoku) were sprinkled and inoculated. Soybeans are cultivated in a greenhouse at 24 ° C. during the daytime and 20 ° C. during the night for 2 days, and then formulated according to the method described in Formulation Example 6, Compounds 1, 4-6, 10-20, 22-29, 31 of the present invention.
  • this compound 1 is mixed with water to a concentration of 200 ppm, and the mixture adheres sufficiently to the leaf surface of the soybean. So that the foliage was sprayed. After spraying, the soybean was air-dried and cultivated in a greenhouse for 9 days, and then the lesion area was examined. As a result, the present compound 1, 4-6, 10-20, 22-29, 31, 33, 34, 37, 38, 42, 46, 50, 58, 61, 63 or soybean treated with the present compound 1 The lesion area was 30% or less of the lesion area in untreated soybean.
  • Test Example 13 Control test against soybean powdery mildew (Microsphaera diffusa) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown therein and cultivated in a greenhouse for 13 days.
  • the present compound 1, 5, 6, 10 to 18, 22, 23, 28, 37 or 38 formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm, The mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the soybean. After spraying, the soybeans were air-dried, and one day later, they were sprinkled with spores of soybean seedlings (variety: Kurosengoku) afflicted with soybean powdery mildew.
  • soybeans were cultivated in a greenhouse at 24 ° C. during the day and 20 ° C. during the night for 11 days, and then the lesion area was examined.
  • the lesion area in the soybean treated with the compound 1, 5, 6, 10 to 18, 22, 23, 28, 37 or 38 of the present invention was 30% or less of the lesion area in the untreated soybean. there were.
  • Test Example 14 Pyrephorophora teres control test A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days.
  • the compound 6, 9, 11, 14, 18 or 24 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 500 ppm, and the mixture is mixed with the above-mentioned barley leaves.
  • the foliage was sprayed so as to adhere well to the surface. After spraying, the barley was air-dried, and two days later, a water suspension of barley reticular fungus spores was spray-inoculated.
  • the barley was placed under high humidity in a greenhouse at 23 ° C. during the daytime and 20 ° C. during the night for 3 days and then cultivated in the greenhouse for 7 days.
  • the lesion area in the barley treated with the present compound 6, 9, 11, 14, 18 or 24 was 30% or less of the lesion area in the untreated barley.
  • This compound has a controlling effect against plant diseases and can be used for controlling plant diseases.

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Abstract

L'invention concerne un procédé de lutte contre des maladies des plantes, ledit procédé comprenant l'application d'un composé représenté par la formule (I) à une plante ou à un sol, et le composé. [Dans la formule (I) : G représente un cycle thiophène, un cycle furane, etc. ; n représente 1, 2, 3 ou 4 ; dans la combinaison de L, X et R2, L représente C(O), X représente une liaison simple, NR3 ou un atome d'oxygène, et R2 représente un groupe alkyle en C1-C6 ayant facultativement un ou plusieurs substituants choisis dans le groupe A, etc. ; R1 représente un groupe alkyle en C1-C6 ayant facultativement un ou plusieurs substituants choisis dans le groupe A, etc., ou R1 et R2 peuvent former, conjointement avec l'atome de carbone auquel R1 et R2 sont attachés, un groupe cycloalkylène à 3 à 7 chaînons, etc. ; R3 représente un groupe alkyle en C1-C6 ayant facultativement un ou plusieurs substituants choisis dans le groupe A, etc. ; et Z représente un groupe cycloalkyle en C3-C6, etc., ou X et Z peuvent former, avec L auquel X et Z sont attachés, un hétérocycle à 4 à 7 chaînons, etc. ]
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WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
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CN112225710A (zh) * 2020-10-14 2021-01-15 华南农业大学 一类含砜杂环类衍生物及其制备方法和应用
CN113024379A (zh) * 2021-03-12 2021-06-25 华东理工大学 一种含羰基化合物及其制备方法和用途
US11091447B2 (en) 2020-01-03 2021-08-17 Berg Llc UBE2K modulators and methods for their use
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WO2021251274A1 (fr) * 2020-06-08 2021-12-16 日本曹達株式会社 Procédé de réduction ou de prévention de l'effet de stress non biologique sur une plante
WO2022138017A1 (fr) * 2020-12-22 2022-06-30 日本農薬株式会社 Composé d'oxadiazole ou son sel, microbicide agricole/horticole contenant ledit composé, et procédé d'utilisation associé
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US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11425910B2 (en) * 2017-02-21 2022-08-30 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2019010192A1 (fr) * 2017-07-05 2019-01-10 Fmc Corporation Oxadiazoles à activité fongicide
TWI821191B (zh) * 2017-07-05 2023-11-11 美商富曼西公司 殺真菌之噁二唑
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US11286242B2 (en) 2018-01-30 2022-03-29 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
US11964967B2 (en) 2018-06-26 2024-04-23 Cytokinetics, Inc. Cardiac sarcomere inhibitors
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
WO2020256113A1 (fr) * 2019-06-21 2020-12-24 日本農薬株式会社 Composé d'oxadiazole ou sels de celui-ci, bactéricide agricole/horticole contenant ledit composé, et procédé d'utilisation associé
CN114585620A (zh) * 2019-06-21 2022-06-03 日本农药株式会社 噁二唑化合物或其盐类及含有该化合物的农园艺用杀菌剂、以及其使用方法
CN114585620B (zh) * 2019-06-21 2024-02-23 日本农药株式会社 噁二唑化合物或其盐类及含有该化合物的农园艺用杀菌剂、以及其使用方法
JP7485667B2 (ja) 2019-06-21 2024-05-16 日本農薬株式会社 オキサジアゾール化合物又はその塩類及び該化合物を含有する農園芸用殺菌剤並びにその使用方法
US11091447B2 (en) 2020-01-03 2021-08-17 Berg Llc UBE2K modulators and methods for their use
WO2021251274A1 (fr) * 2020-06-08 2021-12-16 日本曹達株式会社 Procédé de réduction ou de prévention de l'effet de stress non biologique sur une plante
CN112225710A (zh) * 2020-10-14 2021-01-15 华南农业大学 一类含砜杂环类衍生物及其制备方法和应用
WO2022138017A1 (fr) * 2020-12-22 2022-06-30 日本農薬株式会社 Composé d'oxadiazole ou son sel, microbicide agricole/horticole contenant ledit composé, et procédé d'utilisation associé
CN113024379A (zh) * 2021-03-12 2021-06-25 华东理工大学 一种含羰基化合物及其制备方法和用途

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