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WO2017110861A1 - Agent de lutte contre les maladies des plantes contenant un compose oxadiazole - Google Patents

Agent de lutte contre les maladies des plantes contenant un compose oxadiazole Download PDF

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Publication number
WO2017110861A1
WO2017110861A1 PCT/JP2016/088074 JP2016088074W WO2017110861A1 WO 2017110861 A1 WO2017110861 A1 WO 2017110861A1 JP 2016088074 W JP2016088074 W JP 2016088074W WO 2017110861 A1 WO2017110861 A1 WO 2017110861A1
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group
nme
optionally
eza14
substituents selected
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Japanese (ja)
Inventor
博人 玉島
祐也 吉本
将起 山本
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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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
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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 a plant disease control agent.
  • Patent Documents 1 and 2 Conventionally, various compounds have been developed to control plant diseases (see Patent Documents 1 and 2).
  • An object of the present invention is to provide a plant disease control agent having an excellent control effect.
  • the present inventors have found that an agent containing a compound represented by the following formula (I) has an excellent control effect against plant diseases. I found it. That is, the present invention is as follows.
  • R twenty three , R twenty four , R twenty five , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 131 And R 132 Each independently has a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A, and may have one or more substituents selected from group A.
  • a C3-C6 cycloalkyl group, a 3-8 membered heterocyclic group optionally having one or more substituents selected from group A, or one or more substituents selected from group A Represents a C6-C10 aryl group, t represents 0, 1 or 2; Y 1 , Y 2 , Y Three , Y Four , Y Five , Y 6 , Y 7 , Y 8 , Y 9 , Y Ten , Y 11 , Y 12 , Y 13 , Y 14 , Y 15 , Y 61 , Y 62 , Y 63 , Y 64 And Y 65
  • Group L a group consisting of a halogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, a C1-C3 alkoxy group optionally having one or more halogen atoms, a cyano group, and a nitro group .
  • Group M halogen atom, hydroxy group, sulfanyl group, C1-C6 alkoxy group optionally having one or more halogen atoms, C1-C6 alkylthio group optionally having one or more halogen atoms, 1 or more A group consisting of a C1-C3 alkylamino group optionally having one halogen atom, a di (C1-C3 alkyl) amino group optionally having one or more halogen atoms, a nitro group, and a cyano group.
  • C3 alkoxy) carbonylimino group (C1-C3 alkyl optionally having one or more halogen atoms) carbonylimino group, C1-C3 alkylimino group optionally having one or more halogen atoms, oxo group A thioxo group, a cyano group, a nitro group, a hydroxy group, a sulfanyl group, a carboxy group, an amino group, or one or more halogen atoms Represents a have C1-C3 chain hydrocarbon group, and one or more of the group consisting or C3-C6 cycloalkyl group which may have a halogen atom.
  • Formula (II) [Where, G x Benzene ring, thiophene ring, furan ring, pyrazole ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyrimidine ring or pyridazine ring (the benzene ring)
  • x which may have one or more substituents selected from A x Is NR 12x Represents an oxygen atom or a sulfur atom
  • R 12x Is the group M x A C1-C6 chain hydrocarbon group optionally having one or more substituents selected from the group M x A C3-C6 cycloalkyl group optionally having one or more substituents selected from Group M x A C1-C6 alkoxy group optionally having one or more substituents selected from (C1-C6 alkyl) carbonyl group
  • R 201x Represents R 200x And R 201x Together with the nitrogen atom to which they are attached, a 3-8 membered non-aromatic heterocyclic group ⁇ the 3-8 membered non-aromatic heterocyclic group is group E x Any one substituent selected from the group D x May have one or more substituents selected from Group D
  • Group E x Group A x A 3- to 8-membered heterocyclic group optionally having one or more substituents selected from Group A x A C6-C10 aryl group optionally having one or more substituents selected from the group A x A group consisting of a C3-C6 cycloalkyl group optionally having one or more substituents selected from.
  • R 23x , R 24x , R 25x , R 26x , R 27x , R 28x , R 29x , R 30x , R 31x , R 32x , R 33x , R 34x , R 35x , R 36x , R 37x , R 38x , R 39x , R 40x , R 41x , R 42x , R 43x , R 44x , R 45x , R 46x , R 47x , R 48x , R 49x , R 50x , R 51x , R 52x , R 53x , R 54x , R 55x , R 56x And R 57x Are each independently group A x A C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group A x A C3-C6 cycloalkyl group optionally having one or more substituents selected from Group A x A 3-8-membered heterocyclic group optionally having one or more substituents selected
  • Group L x A group consisting of a halogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, a C1-C3 alkoxy group optionally having one or more halogen atoms, a cyano group, and a nitro group.
  • Group M x Halogen atom, hydroxy group, sulfanyl group, 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 halogens A group consisting of a C1-C3 alkylamino group optionally having atoms, a di (C1-C3 alkyl) amino group optionally having one or more halogen atoms, a nitro group, and a cyano group.
  • R 59x , R 60x , R 61x , R 62x , R 63x , R 64x , R 65x , R 66x , R 67x , R 68x , R 69x , R 70x , R 71x , R 72x , R 73x , R 74x , R 75x , R 76x , R 77x , R 78x , R 79x , R 80x , R 81x , R 82x , R 83x , R 84x , R 85x , R 86x , R 87x , R 88x , R 89x , R 90x , R 91x , R 92x And R 93x Are each independently group B x A C1-C3 chain hydrocarbon group optionally having one or more substituents selected from Group B x A C3-C6 cycloalkyl group optionally having one or more substituents selected from
  • C3 alkoxy) carbonylimino group (C1-C3 alkyl optionally having one or more halogen atoms) carbonylimino group, C1-C3 alkylimino group optionally having one or more halogen atoms, oxo group A thioxo group, a cyano group, a nitro group, a hydroxy group, a sulfanyl group, a carboxy group, an amino group, or one or more halogen atoms Represents a have C1-C3 chain hydrocarbon group, and one or more of the group consisting or C3-C6 cycloalkyl group which may have a halogen atom. ] (Hereinafter referred to as the present compound).
  • R 200x And R 201x Together with the nitrogen atom to which they are attached form a 4-7 membered non-aromatic heterocyclic group, the 4-7 membered non-aromatic heterocyclic group comprising a group D x May have one or more substituents selected from the group E. x A plurality of groups D which may have one substituent selected from x The substituent selected from [2] may be the same or different.
  • [4] 4-7 membered non-aromatic heterocyclic group is group D x
  • Group D x A plurality of groups D which may have one substituent selected from x The substituents selected may be the same or different.
  • Group D x A 4-7-membered non-aromatic heterocyclic group optionally having 1 or 2 substituents selected from azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, Oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, 1,3-thiazinyl group, piperazinyl group, or hexahydropyridazinyl Group (the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1
  • NR 200x R 201x Is represented by formula (E1) -formula (E27) ⁇ Wherein # represents the bonding position with the carbon atom, R 1 , R 2 , R Three , R Four , R Five , R 6 , R 7 , R 8 , R 9 And R Ten Each independently represents a hydrogen atom, a halogen atom, a C1-C3 chain hydrocarbon group optionally having one or more halogen atoms, and a C1-C3 alkoxy group optionally having one or more halogen atoms.
  • R 11 Is a hydrogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, a (C1-C3 alkyl optionally having one or more halogen atoms) carbonyl group, or (one or more halogen atoms).
  • a C1-C3 alkyl) carbonyloxy group which may have a (C1-C3 alkyl optionally having one or more halogen atoms) carbonylthio group.
  • One group selected from the group consisting of formulas (E1) to (E27) is one group selected from the group consisting of formula (E14) to formula (E26), and A x Is an oxygen atom and X x Is an oxygen atom and G x Is group L x
  • C1-C6 Alky Group oxo group, (C1-C6 alkoxy) carbonyl group, hydroxy group, C1-C6 alkoxy group, C1-C3 alkylamino group, di (C1-C3 alkyl) amino group, cyano group and C1-C6 alkoxyimino group It may have one or more substituents selected from the group consisting of, and may have one phenyl group.
  • ⁇ The compound according to [2].
  • R 300 And R 301 Together with the nitrogen atom to which they are attached form a 4-7 membered non-aromatic heterocyclic group, the 4-7 membered non-aromatic heterocyclic group comprising the group D x May have one or more substituents selected from the group E.
  • x A plurality of groups D which may have one substituent selected from x
  • the plant disease control agent according to [1], wherein the substituents selected may be the same or different.
  • NR 300 R 301 Azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group, 1,2-oxazinyl group 1,3-oxazinyl group, 1,3-thiazinyl group, piperazinyl group, or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, Oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group,
  • a plurality of groups D which may have one substituent selected from x The substituents selected may be the same or different.
  • G is group L x
  • a pest control composition further comprising:
  • plant diseases can be controlled.
  • the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “chain hydrocarbon group” represents an alkyl group, an alkenyl group, and an alkynyl group. Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group 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.
  • Examples of the “di (C1-C3 alkyl) amino group optionally having one or more halogen atoms” include a dimethylamino group, a methyl (3,3,3-trifluoropropyl) amino group, and 2,2 -Difluoroethyl (3-chloro-3,3-difluoropropyl) amino group.
  • (C1-C6 alkyl) carbonyl group means a carbonyl group to which a C1-C6 alkyl group is bonded, and examples thereof include an acetyl group and a hexylcarbonyl group.
  • “(C1-C6 alkoxy) carbonylimino group optionally having one or more substituents selected from group A” means C1-C1 optionally having one or more substituents selected from group A. It means a carbonyl group to which C6 alkoxy is bonded, and examples thereof include benzyloxycarbonylimino group and ethoxycarbonylimino group.
  • (C1-C6 alkyl optionally having one or more substituents selected from group A) carbonylimino group means C1-C1 optionally having one or more substituents selected from group A. This means a carbonyl group to which C6 alkyl is bonded, and examples thereof include a benzylcarbonylimino group and an ethylcarbonylimino group.
  • the “3-8 membered heterocyclic group” represents a 3-8 membered non-aromatic heterocyclic group or a 5-6 membered aromatic heterocyclic group.
  • the 3-8 membered non-aromatic heterocyclic group include aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, azacyclooctyl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, Isoxazolidinyl group, morpholino group, thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, 1,3-thiazinyl group, piperazinyl group, tetrahydropyridazinyl group, hexahydropyridazini Group, tetrahydropyrimidiny
  • Examples of the 5-6-membered aromatic heterocyclic group include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl Group, pyridyl group, pyridazinyl group, pyrimidinyl group and pyrazinyl group.
  • Examples of the 3-8-membered non-aromatic heterocyclic group optionally having one or more substituents selected from group D include the groups shown below ( ⁇ represents the bonding position with a carbon atom). Can be mentioned.
  • the “C6-C10 aryl group” represents a phenyl group or a naphthyl group.
  • the compound of the present invention containing one or more asymmetric centers includes each optical isomer and a mixture containing them in an arbitrary ratio.
  • 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 acid addition salts such as hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. May form.
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby acid addition salts such as hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. May form.
  • Examples of the compound of the present invention include the following compounds.
  • E x is E14, E18 or E26, compound.
  • a compound of the present invention, wherein E x is any one of E14-E26.
  • the compound of the present invention, wherein A x is an oxygen atom.
  • the compound of the present invention, wherein X x is an oxygen atom.
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x .
  • the compound of the present invention, wherein G x is a phenyl group.
  • a x is an oxygen atom and X x is an oxygen atom.
  • E x is E14, E18 or E26
  • a x is an oxygen atom
  • X x is an oxygen atom.
  • E x is E14, E18 or E26
  • G x is a phenyl group which may have one or more atoms or groups selected from group L x .
  • E x is E14, E18 or E26
  • G x is a phenyl group.
  • E x is any one of E14 to E26, A x is an oxygen atom, and X x is an oxygen atom.
  • the compound of the present invention, wherein E x is any one of E14-E26 and G x is a phenyl group.
  • a x is an oxygen atom
  • X x is an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from the group L x .
  • a x is an oxygen atom
  • X x is an oxygen atom
  • G x is a phenyl group.
  • E x is E14, E18 or E26
  • a x is an oxygen atom
  • X x is an oxygen atom
  • G x has one or more atoms or groups selected from the group L x
  • a compound that is an optionally substituted phenyl group In the compound of the present invention, E x is any one of E14 to E26, A x is an oxygen atom, X x is an oxygen atom, and G x has one or more atoms or groups selected from the group L x.
  • E x is E14, E18 or E26
  • a x is an oxygen atom
  • X x is an oxygen atom
  • G x is a phenyl group.
  • E x is any one of E14 to E26
  • a x is an oxygen atom
  • X x is an oxygen atom
  • G x is a phenyl group.
  • E x is azetidinyl, pyrrolidinyl, piperidinyl, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, a morpholino group, Thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, piperazinyl group or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group
  • E x is a pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group or thiomorpholino group ⁇ the pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group and thiomorpholino group are selected from group D x And may further have one substituent selected from the group E x . ⁇ The compound which is.
  • E x is a pyrrolidinyl group or piperidinyl group (the pyrrolidinyl group and piperidinyl group may have one or more substituents selected from group D x, and are selected from group E x It may further have one substituent.
  • ⁇ The compound which is.
  • E x is a pyrrolidinyl group (the pyrrolidinyl group may have one or more substituents selected from group D x, and one substituent selected from group E x is further added). You may have. ⁇ The compound which is.
  • E x is a piperidinyl group (the piperidinyl group may have one or more substituents selected from group D x, and one substituent selected from group E x is further added). You may have. ⁇ The compound which is.
  • E x is a morpholino group (the morpholino group may have one or more substituents selected from group D x, and further includes one substituent selected from group E x You may have. ⁇ The compound which is.
  • E x is a thiomorpholino group (the thiomorpholino group may have one or more substituents selected from group D x , and one substituent selected from group E x May further be included.
  • ⁇ The compound which is.
  • E x is a piperazinyl group (the piperazinyl group may have one or more substituents selected from group D x, and one substituent selected from group E x is further added. You may have. ⁇ The compound which is.
  • E x is an oxazolidinyl group (the oxazolidinyl group may have one or more substituents selected from group D x, and further includes one substituent selected from group E x You may have. ⁇ The compound which is.
  • E x is a thiazolidinyl group (the thiazolidinyl group may have one or more substituents selected from group D x, and one substituent selected from group E x is further added. You may have. ⁇ The compound which is.
  • E x is azetidinyl, pyrrolidinyl, piperidinyl, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, a morpholino group, Thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, piperazinyl group or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group, 1,
  • E x is a pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group or thiomorpholino group ⁇ the pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group and thiomorpholino group are selected from group D x It may have one or more substituents. ⁇ The compound which is.
  • E x may have a pyrrolidinyl group or a piperidinyl group (the pyrrolidinyl group and piperidinyl group may have one or more substituents selected from the group D x .
  • the compound which is. [Aspect 14] A compound in which E x is a pyrrolidinyl group optionally having one or more substituents selected from group D x in the compound of the present invention.
  • a compound in which E x is a piperidinyl group optionally having one or more substituents selected from group D x in the compound of the present invention.
  • E x is a piperazinyl group optionally having one or more substituents selected from group D x .
  • E x is azetidinyl, pyrrolidinyl, piperidinyl, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, a morpholino group, Thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, piperazinyl group or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group, 1,
  • E x is a pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group or thiomorpholino group ⁇ the pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholino group and thiomorpholino group are selected from group D x It may have one substituent. ⁇ The compound which is. [Aspect 23] In the compound of the present invention, E x may have a pyrrolidinyl group or a piperidinyl group (the pyrrolidinyl group and piperidinyl group may have one substituent selected from the group D x .
  • E x is azetidinyl, pyrrolidinyl, piperidinyl, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, a morpholino group, Thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, piperazinyl group or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholin
  • E x is a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholino group or a thiomorpholino group ⁇ said pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholino group and a thiomorpholino group, a phenyl group, a phenyl it may have one or more substituents selected from the group consisting of optionally C1-C3 may be alkyl groups and the group B x has a group.
  • E x is a pyrrolidinyl group or piperidinyl group (the pyrrolidinyl group and piperidinyl group are a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and a group consisting of group B x It may have one or more substituents selected.
  • ⁇ The compound which is.
  • E x has a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x has a phenyl group, a C1-C3 alkyl group which may have a phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x has a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one or more substituents selected from the group consisting of group B x.
  • a compound that is a good morpholino group is
  • E x has a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x has a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x has a phenyl group, a C1-C3 alkyl group which may have a phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x has a phenyl group, a C1-C3 alkyl group which may have a phenyl group, and one or more substituents selected from the group consisting of group B x.
  • E x is azetidinyl, pyrrolidinyl, piperidinyl, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, a morpholino group, Thiomorpholino group, 1,2-oxazinyl group, 1,3-oxazinyl group, piperazinyl group or hexahydropyridazinyl group ⁇ the azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl group, pyrazolidinyl group, imidazolidinyl group Group, oxazolidinyl group, thiazolidinyl group, isoxazolidinyl group, morpholino group, thiomorpholino group, 1,
  • E x is a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholino group or a thiomorpholino group ⁇ said pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholino group and a thiomorpholino group, a phenyl group, a phenyl it may have one substituent chosen from the group consisting of may also be C1-C3 alkyl group and the group B x have group.
  • E x is a pyrrolidinyl group or a piperidinyl group ⁇ the pyrrolidinyl group and piperidinyl group are a phenyl group, a C1-C3 alkyl group optionally having a phenyl group, and a group consisting of group B x You may have 1 substituent chosen from more. ⁇ The compound which is. [Aspect 44] In the compound of the present invention, E x may have a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one substituent selected from the group consisting of group B x. A compound that is a good pyrrolidinyl group.
  • E x may have a phenyl group, a C1-C3 alkyl group which may have a phenyl group, and one substituent selected from the group consisting of group B x.
  • E x may have a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one substituent selected from the group consisting of group B x.
  • a compound that is a good morpholino group is a compound that is a good morpholino group.
  • E x may have a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one substituent selected from the group consisting of group B x.
  • E x may have a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one substituent selected from the group consisting of group B x.
  • E x may have a phenyl group, a C1-C3 alkyl group optionally having phenyl group, and one substituent selected from the group consisting of group B x.
  • E x may have a phenyl group, a C1-C3 alkyl group which may have a phenyl group, and one substituent selected from the group consisting of group B x.
  • Aspect 52 The compound according to any one of Aspects 1 to 50, wherein A x is an oxygen atom.
  • Aspect 53 The compound according to any one of Aspects 1 to 50, wherein X x is an oxygen atom.
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x
  • a x is a para group with respect to the oxadiazole ring.
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x , and A x is a para group with respect to the oxadiazole ring.
  • a compound that binds to a position [Aspect 56] The compound according to any one of aspects 1 to 50, wherein G x is a phenyl group, and A x is bonded to the para-position or the meta-position with respect to the oxadiazole ring.
  • Aspect 57 The compound according to any one of aspects 1 to 50, wherein G x is a phenyl group and A x is bonded to the para-position relative to the oxadiazole ring.
  • Aspect 58 The compound according to any one of Aspects 1 to 50, wherein A x is NR 12x or an oxygen atom, and X x is an oxygen atom.
  • a x is NR 12x or an oxygen atom
  • X x is an oxygen atom.
  • Embodiment 1 ⁇ 50 A x is an oxygen atom, and X x is an oxygen atom.
  • X x is an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x
  • a x is A compound bonded to the para-position or meta-position with respect to the oxadiazole ring.
  • X x is an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x
  • a x is A compound bonded to the para position relative to the oxadiazole ring.
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x , A compound in which A x is bonded to the para-position or the meta-position with respect to the oxadiazole ring.
  • a x is an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x
  • a x is A compound bonded to the para-position or meta-position with respect to the oxadiazole ring.
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group optionally having one or more atoms or groups selected from group L x , A compound in which A x is bonded to the para-position relative to the oxadiazole ring.
  • a x is an oxygen atom
  • G x is a phenyl group which may have one or more atoms or groups selected from group L x
  • a x is A compound bonded to the para position relative to the oxadiazole ring.
  • a x is an oxygen atom
  • G x is a phenyl group
  • a x is bonded to the para position or the meta position with respect to the oxadiazole ring.
  • Aspect 70 The compound according to any one of Aspects 1 to 50, wherein A x is NR 12x or an oxygen atom, G x is a phenyl group, and A x is bonded to the para position with respect to the oxadiazole ring.
  • Aspect 71 The compound according to any one of Aspects 1 to 50, wherein A x is an oxygen atom, G x is a phenyl group, and A x is bonded to the para position with respect to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x has one or more atoms or groups selected from group L x.
  • X x may be an oxygen atom
  • a x may be an oxygen atom
  • G x may have one or more atoms or groups selected from group L x.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x has one or more atoms or groups selected from group L x.
  • X x may be an oxygen atom
  • a x may be an oxygen atom
  • G x may have one or more atoms or groups selected from the group L x.
  • a compound which is a phenyl group and A x is bonded to the para position with respect to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group
  • a x is a para group relative to the oxadiazole ring.
  • Embodiment 1 ⁇ 50 X x is an oxygen atom
  • a x is an oxygen atom
  • G x is a phenyl group
  • para or meta A x is relative to the oxadiazole ring A compound that binds to a position.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group
  • a x is para to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is an oxygen atom
  • G x is a phenyl group
  • a x is bonded to the para position with respect to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group
  • a x is in a para-position or meta to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is an oxygen atom
  • G x is a phenyl group
  • a x is bonded to the para position or the meta position with respect to the oxadiazole ring.
  • X x is an oxygen atom
  • a x is NR 12x or an oxygen atom
  • G x is a phenyl group
  • a x is bonded to the para position with respect to the oxadiazole ring.
  • G x is a benzene ring
  • a x is an oxygen atom
  • X x is an oxygen atom
  • E x is an azetidinyl group, pyrrolidinyl group, piperidinyl group, azepan-1-yl Group
  • pyrazolidinyl group imidazolidinyl group
  • oxazolidinyl group thiazolidinyl group
  • the compound represented by the formula (I) can be produced, for example, by the following production method.
  • the compound represented by formula (I) is a compound represented by formula (A1) (hereinafter referred to as compound (A1)) and a compound represented by formula (A2) (hereinafter referred to as compound (A2)) or It can be produced by reacting the salt in the presence of a base.
  • the reaction is usually performed in a solvent.
  • 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.
  • Ethers such as methyl tert-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, Acid amides such as 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone (hereinafter referred to as acid amides), esters such as ethyl acetate and methyl acetate (hereinafter referred to as esters) , Sulfoxides such as dimethyl sulfoxide (hereinafter referred to as "su Referred to as sulfoxide compound.), Nitriles such as acetonitrile and propionitrile (hereinafter, referred to as nitriles.) And mixtures thereof.
  • ethers Ethers such as methyl tert-butyl ether and diisoprop
  • 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. , Bicarbonates such as sodium bicarbonate, and mixtures thereof.
  • Examples of the salt of compound (A2) include hydrochloride or sulfate.
  • the compound (A2) is usually used in a proportion of 1 to 10 mol and the base is used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (A1).
  • 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 represented by the formula (I) can be isolated by performing post-treatment operations such as extraction of the mixture with an organic solvent, and drying and concentration of the organic layer.
  • Compound (A1) and compound (A2) or a salt thereof are known or can be produced according to known methods.
  • the compound of the present invention can be produced by reacting the compound represented by the formula (A x 1) with the compound represented by the formula (A x 2) or a salt thereof in the presence of a base. [Wherein the symbols have the same meaning as described above. ] The reaction can be carried out according to the method described in Production Method A.
  • the compound represented by formula (I) is a compound represented by formula (A3) (hereinafter referred to as compound (A3)) and a compound represented by formula (A4) (hereinafter referred to as compound (A4)) or It can be produced by reacting the salt in the presence of a base.
  • the salt of compound (A4) include hydrochloride or sulfate. The reaction was carried out in Org. Lett. , 2002, 4 (11), 1859-1862.
  • Compound (A3) and compound (A4) or a salt thereof are known or can be produced according to a known method.
  • Manufacturing method B x The compound of the present invention can be produced by reacting a compound represented by the formula (A x 3) with a compound represented by the formula (A x 4) or a salt thereof in the presence of a base. [Wherein the symbols have the same meaning as described above. ] The reaction can be carried out according to the method described in Production Method B.
  • a compound represented by formula (A6) (hereinafter referred to as compound (A6)) is a compound represented by formula (A5) (hereinafter referred to as compound (A5)), an oxidizing agent, and the like.
  • A represents NR 12XX or an oxygen atom
  • R 12XX represents C1 —C6 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C6 alkoxy group, or (C1-C6 alkyl) carbonyl group.
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, and mixtures thereof.
  • Examples of the oxidizing agent used in the reaction include Dess-Martin periodinane and pyridinium chlorochromate.
  • 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 (A6) 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.
  • a compound represented by formula (A8) (hereinafter referred to as compound (A8)) is represented by compound (A6) and a compound represented by formula (A7) (hereinafter referred to as compound (A7)).
  • the reaction is usually performed in a solvent. Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, methanol, ethanol and other alcohols (hereinafter referred to as alcohols). , Water and mixtures thereof.
  • Compound (A7) may be in the form of a salt.
  • Examples of the salt of compound (A7) include hydrochloride or sulfate.
  • compound (A7) is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (A6).
  • 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 (A8) 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.
  • a compound represented by formula (A10) (hereinafter referred to as compound (A10)) is represented by compound (A6) and a compound represented by formula (A9) (hereinafter referred to as compound (A9)).
  • compound (A10) is represented by compound (A6) and a compound represented by formula (A9) (hereinafter referred to as compound (A9)).
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
  • the acid used for the reaction examples include p-toluenesulfonic acid, hydrochloric acid, trifluoroacetic acid and the like.
  • the acid salt used in the reaction examples include O-methylhydroxylamine hydrochloride and O-ethylhydroxylamine hydrochloride.
  • 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 (A10) 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.
  • Each compound produced by the above production method and reference production method can also be isolated by other known means such as concentration, concentration under reduced pressure, extraction, phase transfer, crystallization, recrystallization, chromatography, etc. -It can be purified.
  • the compound of the present invention may be used alone.
  • the compound of the present invention is mixed with a solid carrier, a liquid carrier, and / or a surfactant, and if necessary, a fixing agent.
  • Dispersants, stabilizers and other formulation aids added, wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol It is used in the form of pharmaceutical preparations and microcapsules.
  • 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, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, calcium carbonate, hydration) And fine particles such as silica) or granular materials.
  • clays for example, kaolin, diatomaceous earth, fusami clay, bentonite, acidic clay
  • talc and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, calcium carbonate, hydration) And fine particles such as silica) or granular materials.
  • 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, acid 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, acid amides, and halogenated hydrocarbon
  • 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, fixing agents, dispersants, and stabilizers.
  • casein gelatin, polysaccharides (eg, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, Saccharides, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2 A mixture of -tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
  • polysaccharides eg, starch, arabic gum, cellulose derivatives, alginic acid
  • lignin derivatives bentonite
  • Saccharides synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrol
  • the compound of the present invention may be used by mixing with various oils such as mineral oil and vegetable oil, or surfactants.
  • Oils that can be specifically mixed and used as surfactants are 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), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N ( Recorded trademark), BANOLE (register
  • the compound of the present invention is applied as the control agent of the present invention.
  • the method of the present invention is not particularly limited as long as the control agent of the present invention can be practically applied, but for example, treatment to plants such as foliage spraying, soil treatment, etc.
  • Treatment seed treatment such as seed disinfection, treatment of harmful arthropods, and the like.
  • the treatment amount of the compound of the present invention depends on the type of plant to be treated, the type and occurrence frequency of plant diseases to be controlled, formulation form, treatment time, treatment method, treatment place, weather conditions, etc.
  • the compound of the present invention is usually 1 to 500 g per 1000 m 2 when it is treated on the foliage of the plant or on the soil where the plant is grown.
  • Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying.
  • the concentration of the compound of the present invention is usually 0.0005 to 2% by weight.
  • Powders, granules, etc. are usually processed without dilution.
  • the compound of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards.
  • the compound of the present invention can control diseases of the cultivated land in the cultivated lands where the “plants” and the like listed below are cultivated.
  • this invention compound can control the harmful arthropod of the said agricultural field.
  • Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplant, tomato, pepper, pepper, potato Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery vegetables (carrots, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants, Fruit trees; pears (apples, pears, Japanese
  • 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.
  • 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 (Blumeria) graminis), red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red snow rot (Microdochium nivale) , Microdochium majus), Snow rot microbe nuclei (Typhula incarnata, Typhula ishikariensis), Bare smut (Ustilago tritici), pine scab (Tilletia
  • 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.
  • Carposinidae Coffee Leaf miner (Leucoptera coffeella), peach leaf moth (Lyonetia clerkella), winged leaf moth (Lyonetia prunifoliella), etc. Lymantriidae such as Euproctis spp.
  • Eumantis genus (Lymantria spp.), Euproctis pseudoconspersa; Plutellidae such as Plutella xylostella; Plumellidae; Helicopteraceae (Gelchiidae) such as Helcystogramma triannulella, Pectinophora gossypiella, potato moth (Phthorimaea operculella); Castnii family (Castnii) dae); Arcticidae (Cossus insularis), etc. (Cossidae); Ascotis selenaria, etc. Staphmopodidae, etc .; Sphingidae, such as Acherontia lachesis; Ssiidae, such as Nokona feralis;
  • 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), Species (Oxya japonica), grasshopper (Patanga succincta), etc. rididae); Gryllotalpida
  • Hymenoptera bee (Athalia rosae), Japanese bee (Athalia japonica) and other bees (Tenthredinidae); fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara) and other ants 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
  • Production Example 1-2 The compounds produced according to the method described in Production Example 1-1 and their physical properties are shown below.
  • Compound 2 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.14 (2H, dt), 7.30 (2H, dt), 3.77 (4H, t), 3.68-3.62 (4H, m).
  • Compound 3 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.13 (2H, dt), 7.30 (2H, dt), 3.69-3.64 (4H, m), 2.48 (4 H, t), 2.36 (3H, s).
  • Production Example 1-3 The compounds produced according to the method described in Production Example 1-1 and their physical properties are shown below.
  • Reference production example 1-1 7.25 g of trifluoroacetic anhydride was added dropwise to a mixture of 5.34 g of N ′, 4-dihydroxy-3-fluorobenzenecarboximidamide, 7.44 g of pyridine, and 48 mL of dimethylformamide, and the mixture was stirred at 80 ° C. for 5 hours.
  • the reaction mixture was diluted with ethyl acetate and washed successively with 2N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine.
  • the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 7.22 g of intermediate 2 shown below.
  • Intermediate 2 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 7.87-7.84 (2H, m), 7.16-7.12 (1H, m), 5.75 (1H, br s).
  • Reference production example 1-2 The compounds produced according to the method described in Reference Production Example 1-1 and their physical properties are shown below.
  • Intermediate 5 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 7.99-7.95 (1H, m), 6.81-6.75 (2H, m), 6.32 (1H, br s).
  • Production Example 2-2 The compounds produced according to the method described in Production Example 2-1 and their physical properties are shown below.
  • Formula (a) [Wherein E Y represents a corresponding substituent shown in each of [Table 1] to [Table 4]. ] Wherein Y is any one of those listed in [Table 1] to [Table 4]. However, ⁇ in [Table 1] to [Table 4] represents a bonding position with a carbon atom.
  • compound 5 is the following compound.
  • Compound 5 of the present invention is the following compound.
  • Production Example 4-2 The compounds produced according to the method described in Production Example 4-1, and their physical properties are shown below.
  • Compound 32 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.15 (2H, d), 7.34-7.28 (2H, m), 4.27 (1H, s), 4.18 (1H, s), 3.92-3.74 (2H, m ), 2.59 (2H, t), 2.20-2.07 (2H, m).
  • Compound 33 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.16 (2H, d), 7.38-7.31 (2H, m), 4.13-3.91 (4H, m), 2.79-2.68 (2H, m).
  • Production Example 5-2 The compounds produced according to the method described in Production Example 5-1 and their physical properties are shown below.
  • Compound 36 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.13 (2H, d), 7.29 (2H, d), 3.73-3.56 (4H, m), 3.24 (6H, s), 1.88-1.79 (4H, m ).
  • Compound 37 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.12 (2H, d), 7.35-7.29 (2H, m), 3.72-3.67 (2H, m), 3.63-3.50 (6H, m), 2.20-2.11 (2H, m), 1.27-1.21 (6H, m).
  • Production Example 6-2 The compounds produced according to the method described in Production Example 6-1 and their physical properties are shown below.
  • Compound 43 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.17 (2H, d), 7.38 (2H, d), 5.12 (1H, s), 4.11 (2H, t), 3.60 (2H, t).
  • Production Example 7-2 The compounds produced according to the method described in Production Example 7-1 and their physical properties are shown below.
  • Compound 53 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.02 (2H, d), 7.52 (2H, d), 6.58 (1H, s), 3.94-3.99 (1H, m), 3.81-3.87 (1H, m ), 3.48-3.54 (1H, m), 3.23-3.30 (1H, m), 2.85-2.92 (1H, m), 1.86-1.99 (2H, m), 1.48-1.65 (2H, m)
  • Compound 54 of the present invention 1 H-NMR (CDCl 3 , 25 ° C) ⁇ : 8.03 (2H, d), 7.51 (2H, d), 6.57 (1H, s), 3.37-3.74 (3H, m), 2.74-3.11 (3H, m ), 1.78-2.00 (3H, m)
  • H represents a hydrogen atom
  • O represents an oxygen atom
  • S represents a sulfur atom
  • N represents a nitrogen atom
  • Cl represents a chlorine atom
  • F represents a fluorine atom
  • Me represents methyl Et represents an ethyl group
  • Pr represents a propyl group
  • Ph represents a phenyl group
  • OMe represents a methoxy group
  • CF3 represents a trifluoromethyl group
  • CH2Ph represents a benzyl group
  • CN represents Represents a cyano group
  • NO2 represents a nitro group
  • COOH represents a carboxy group
  • OH represents a hydroxy group
  • SH represents a sulfanyl group
  • NH2 represents an amino group
  • Formula (T1) In which the combination of E Z , X and A is a combination described in any one of the substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by the formula (T1), the substituent number ZA1 To ZA3368 are represented as compounds of the present invention ZA1 to ZA3368, respectively, and the compounds of the present invention ZA1 to ZA3368 are collectively represented as compound of the present invention SX1) can be produced according to the above production method.
  • E Z represents one of the following formulas (EZA1) to (EZA44).
  • # represents a bonding position with a carbon atom.
  • Substituent number ZA1 to substituent number ZA3368 are a compound represented by formula (T1), a compound represented by formula (T2), a compound represented by formula (T3), a compound represented by formula (T4), (T5) compound represented by a compound represented by the formula (T6), in the compound represented by formula (T7) compounds or formula represented by (T8), E Z, X and a, and corresponds to the structure of E Z Represents a combination of substituents R 400 , R 401 , R 402 and R 403 , and hereinafter, [substituent numbers; E Z , R 400 , R 401 , R 402 , R 403 , X, A] and I write.
  • the substituent number ZA2 is that E Z is EZA1
  • R 400 is a methyl group
  • R 401 , R 402 and R 403 are hydrogen atoms
  • X is an oxygen atom
  • A is NH. Represents a combination.
  • [ZA1301; EZA1, H, CH2NH2, H, H, O, S], [ZA1302; EZA1, H, NHC ( O) CH3, H, H, O, S], [ZA1303; EZA1, H, CH2Ph, H, H, O, S], [ZA1304; EZA1, H, 1-pyrrolidinyl, H, H, O, S], [ZA1305; EZA1, H, 1-piperidinyl, H, H, O, S], [ZA1306; EZA1, H, Me, Me, H, O, S], [ZA1307; EZA1, H, Et, Et, H, O, S], [ZA1308; EZA1, H, OMe, OMe, H, O, S], [ZA1309; EZA1, H, OEt, OEt, H, O, S], [ZA1310; EZA1, H, OPr, OPr, H, O, S], [ZA1311; EZA2, H, H, H, H, O, S], [
  • [ZA2401; EZA27, H, CH2NH2, H, H, S, NMe], [ZA2402; EZA27, H, NHC ( O) CH3, H, H, S, NMe], [ZA2403; EZA27, H, CH2Ph, H, H, S, NMe], [ZA2404; EZA27, H, 1-pyrrolidinyl, H, H, S, NMe], [ZA2405; EZA27, H, 1-piperidinyl, H, H, S, NMe], [ZA2406; EZA28, H, H, H, S, NMe], [ZA2407; EZA28, Me, H, H, S, NMe], [ZA2408; EZA28, H, Me, H, H, S, NMe], [ZA2409; EZA29, H, H, H, S, NMe], [ZA2410; EZA29, Me, H, H, H, S, NMe], [ZA2410; EZA29,
  • the compound ZA2 of the present invention means a compound having the substituent number ZA2 in the compound represented by the formula (T1), E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T1).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • Formula (T2) In the compound represented by formula (T2), the combination of E Z , X and A is a combination described in any one of the substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by the formula (T2), the substituent number ZA1 To ZA3368 are represented as compounds of the present invention ZB1 to ZB3368, respectively, and the compounds of the present invention ZB1 to ZB3368 are collectively represented as compound of the present invention SX2).
  • the compound of the present invention ZB2 means a compound having the substituent number ZA2 in the compound represented by the formula (T2), E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T2).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • Formula (T3) In which the combination of E Z , X and A is a combination described in any one of the substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by the formula (T3), the substituent number ZA1 To ZA3368 are represented as compounds of the present invention ZC1 to ZC3368, and the compounds of the present invention ZC1 to ZC3368 are collectively represented as compound of the present invention SX3).
  • the compound of the present invention ZC2 means a compound having the substituent number ZA2 in the compound represented by the formula (T3), E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T3).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • Formula (T4) In which the combination of E Z , X and A is a combination described in any one of substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by formula (T4), the substituent number ZA1 To ZA3368 are represented by the present compounds ZD1 to ZD3368, and the present compounds ZD1 to ZD3368 are collectively represented by the present compound SX4).
  • the compound of the present invention ZD2 means a compound having the substituent number ZA2 in the compound represented by the formula (T4).
  • E Z is EZA1
  • R 400 is methyl.
  • R 401, R 402 and R 403 are hydrogen atoms
  • X is an oxygen atom
  • a compound represented by the following a is NH.
  • Formula (T5) In which the combination of E Z , X and A is a combination described in any one of the substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by the formula (T5), the substituent number ZA1 To ZA3368 are represented by the present compounds ZE1 to ZE3368, respectively, and the present compounds ZE1 to ZE3368 are collectively represented by the present compound SX5), and can be produced according to the above production method.
  • the compound ZE2 of the present invention means a compound having the substituent number ZA2 in the compound represented by the formula (T5), E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T5).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • Formula (T6) In which the combination of E Z , X and A is a combination described in any one of substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by formula (T6), the substituent number ZA1 To ZA3368 are represented by the present compounds ZF1 to ZF3368, and the present compounds ZF1 to ZF3368 are collectively represented by the present compound SX6).
  • the compound of the present invention ZF2 means a compound having the substituent number ZA2 in the compound represented by the formula (T6), E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T6).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • Formula (T7) In which the combination of E Z , X and A is a combination described in any one of the substituent numbers ZA1 to ZA3368 (hereinafter, in the compound represented by the formula (T7), the substituent number ZA1 To ZA3368 are represented by the compounds of the present invention ZG1 to ZG3368, respectively, and the compounds of the present invention ZG1 to ZG3368 are collectively represented by the present compound SX7).
  • the compound of the present invention ZG2 means a compound having the substituent number ZA2 in the compound represented by the formula (T7).
  • E Z is EZA1
  • R 400 is methyl.
  • R 401 , R 402 and R 403 are hydrogen atoms
  • X is an oxygen atom
  • A is NH.
  • the compound of the present invention ZH2 means a compound having the substituent number ZA2 in the compound represented by the formula (T8), and E Z is EZA1 and R 400 is methyl in the compound represented by the formula (T8).
  • R 401 , R 402 and R 403 are hydrogen atoms, X is an oxygen atom, and A is NH.
  • the compound of the present invention can be used in combination or in combination with plant disease control agents such as fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists (hereinafter referred to as “this component”). It can.
  • this component plant disease control agents
  • fungicides insecticides, acaricides, nematocides, plant growth regulators or synergists
  • this component fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists
  • this component fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists
  • the ratio of the compound of the present invention to the active ingredient is not particularly limited, but the weight ratio (the compound of the present invention: the active ingredient) is, for example, 1000: 1 to 1: 1000, 500: 1 to 1: 500. 100: 1 to 1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1 1: 1 to 1: 100, 1: 1 to 1:50, 1: 1 to 1:20, and 1: 1 to 1:10.
  • Formulation Example 1 A formulation is obtained by thoroughly pulverizing and mixing 50 parts of SX, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.
  • Formulation Example 2 After 20 parts of SX and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet grinding method, 0.05 parts of xanthan gum and 40 parts of an aqueous solution containing 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and mixed by stirring to obtain a preparation.
  • Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of SX, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of SX, 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 SX, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, adding water and kneading and granulating and drying, A formulation is obtained.
  • Formulation Example 6 SX 20 parts; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water were mixed to make a total amount of 100 parts, and processed using a pulverizer. A formulation is obtained.
  • test examples are shown.
  • the untreated section in Test Example 1 to Test Example 3 was performed under the same conditions as described in each test example, except that dimethyl sulfoxide was dispensed instead of the dimethyl sulfoxide diluted solution containing the compound of the present invention.
  • the term “no treatment” in Test Example 4 to Test Example 19 indicates that the mixture of the preparation containing the compound of the present invention and water was not sprayed.
  • the control effect is obtained by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion on the plant treated with the compound of the present invention with the area of the lesion on the untreated plant. evaluated.
  • Test Example 1 Control test against tomato leaf mold (Cladosporium fulvum) 1500 ppm of present compound 1, 4, 5, 8, 9, 16, 17, 20, 21, 25, 31, 35, 37, 38 or 42 After diluting with dimethyl sulfoxide and dispensing 1 ⁇ L into a titer plate (96-well), the 129th amino acid residue of cytochrome b was changed from phenylalanine to leucine in advance. 150 ⁇ L of a potato broth liquid medium (PDB medium) inoculated with spores of a QoI resistant strain whose base sequence was mutated so as to be replaced was dispensed. This plate was cultured at 18 ° C.
  • PDB medium potato broth liquid medium
  • the growth degree in the group treated with the compound 1, 4, 5, 8, 9, 16, 17, 20, 21, 25, 31, 35, 37, 38 or 42 of the present invention is all in the untreated group. It was 50% or less of the degree of growth.
  • Test Example 2 Control Test against Wheat Leaf Blight Fungus (Septoria tritici) Compound 1, 2, 4, 5, 8, 9, 10, 11, 14, 15, 16, 17, 18, 19, 20, 21, 24 of the present invention , 25, 27, 28, 29, 31, 33, 35, 38 or 42, diluted with dimethyl sulfoxide so as to contain 1500 ppm, dispensed 1 ⁇ L into a titer plate (96 well), and then pre-spores of wheat leaf blight fungus 150 ⁇ L of the potato broth liquid medium (PDB medium) inoculated with the above was dispensed. This plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight fungi.
  • 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 33, 35, 38 or 42 was 50% or less of the growth degree in the untreated section.
  • Test Example 3 Control test against soybean anthracnose fungus (Colletotrichum truncatum)
  • the compound 1, 4, 5, 8, 9, 20, 21 or 35 of the present invention was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and the titer plate (96 wells) was diluted. After 1 ⁇ L was dispensed, 150 ⁇ L of a potato broth liquid medium (PDB medium) inoculated with spores of soybean anthrax in advance was dispensed. This plate was cultured at 18 ° C.
  • PDB medium potato broth liquid medium
  • the growth degree in the group treated with the present compound 1, 4, 5, 8, 9, 20, 21 or 35 was 50% or less of the growth degree in the untreated group.
  • Test Example 4 Control test against Pyrenophora teres A plastic pot was filled with soil, and barley (cultivar; Nishinohoshi) was seeded there and allowed to grow in a greenhouse for 7 days.
  • the present compound 1, 8, 15, 16, 18, 25, 26, 27, 30, 34, 35, 45, 46, 49, 51 or 54 formulated according to the method described in Formulation Example 6, It mixed with water so that a density
  • 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. As a result, there was no lesion area in the barley treated with the compound 1, 8, 15, 16, 18, 25, 26, 27, 30, 34, 35, 45, 46, 49, 51 or 54 of the present invention. It was 30% or less of the lesion area in the treated barley.
  • Test Example 5 Pyrenophora teres control test A plastic pot was filled with soil, and barley (variety: Nishinohoshi) was seeded there and allowed to grow in a greenhouse for 7 days.
  • the compound of the present invention 7, 11, 17, 28, 31, 36, 39, 40, 46, 49, or 50 formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm. Then, the mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the barley. 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 7, 11, 17, 28, 31, 36, 39, 40, 46, 49 or 50 is 30% of the lesion area in the untreated barley. It was the following.
  • Test Example 6 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and allowed to grow in a greenhouse for 20 days. Thereafter, the present compound 2, 3, 4, 5, 9, 10, 14, 15, 18, 20, 24, 25, 26, 28, 45, 47 formulated according to the method described in Formulation Example 6. 49 or 50 was mixed with water to a concentration of 500 ppm, and the mixture was sprayed on the foliage so as to adhere well to the leaf surface of the rice.
  • 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 rice treated with the compound 2, 3, 4, 5, 9, 10, 14, 15, 18, 20, 24, 25, 26, 28, 45, 47, 49, or 50 of the present invention was All were 30% or less of the lesion area in untreated rice.
  • Test Example 7 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown therein, and allowed to grow in a greenhouse for 20 days. Thereafter, the compound of the present invention 17, 19, 27, 31, 38, 39 or 54 formulated according to the method described in Formulation Example 6 was mixed with water to a concentration of 200 ppm, and the mixture was The foliage was sprayed so as to adhere well to the leaf surface of 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 17, 19, 27, 31, 38, 39 or 54 was 30% or less of the lesion area in the untreated rice.
  • Test Example 8 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was seeded there and allowed to grow in a greenhouse for 10 days.
  • the compound of the present invention 12, 26, 32, 45, 46, 47, 48, 51, or 54 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. Then, the stems and leaves were sprayed so as to adhere well to the leaves of the wheat. After spraying, the wheat was air-dried, and after 4 days, an aqueous suspension of wheat leaf blight spores was spray-inoculated.
  • the wheat was placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined.
  • the lesion area in the wheat treated with the present compound 12, 26, 32, 45, 46, 47, 48, 51 or 54 was 30% or less of the lesion area in the untreated wheat. .
  • Test Example 9 Control Trial for Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was seeded there, and allowed to grow in a greenhouse for 10 days.
  • Compound 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 13, 14, 16, 17, 18, 19, 20 formulated according to the method described in Formulation Example 6 21, 22, 24, 27, 28, 29, 30, 31, 33, 34, 35, 36, 37, 38, 40, 41, 42, 44, 45, 46, 48, 49, 50, 53 or 54 was mixed with water so as to have 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.
  • the wheat After spraying, the wheat was air-dried, and after 4 days, an aqueous suspension of wheat leaf blight spores was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the compounds 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 13, 14, 16, 17, 18, 19, 20, 21, 22, 24, 27, 28, 29, 30, 31, 33, 34, 35, 36, 37, 38, 40, 41, 42, 44, 45, 46, 48, 49, 50, 53 or 54 The lesion area in untreated wheat was 30% or less.
  • Test Example 10 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and then wheat (cultivar; apogee) was seeded there, grown 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 formulated according to the method described in Formulation Example 6, 1, 2, 3, 4, 5, 8, 9, 10, 14, 17, 19, 20, 24, 27, 29, 30, 31, 33, 34, 35, 36, 37, 38, 40, 41, 45 or 50 is 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.
  • the wheat was air-dried and placed under illumination for 14 to 18 days, and then the lesion area was examined.
  • the lesion area in the wheat treated with 38, 40, 41, 45 or 50 was 30% or less of the lesion area in the untreated wheat.
  • Test Example 11 Control test against wheat rust (Puccinia recondita) A plastic pot was filled with soil, and then wheat (cultivar: Shirogane) was sown therein and allowed to grow in a greenhouse for 9 days.
  • the present compound 16, 20, 21, 22, 26, 28, 45, 49, 50, 51, or 52 formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration is 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 cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus. After inoculation, the wheat was placed in a dark and humid environment at 23 ° C.
  • the lesion area in the wheat treated with the present compound 16, 20, 21, 22, 26, 28, 45, 49, 50, 51 or 52 is 30% of the lesion area in the untreated wheat. It was the following.
  • Test Example 12 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, seeded with wheat (cultivar: Shirogane), and grown in a greenhouse for 9 days. Compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 17, 18 formulated according to the method described in Formulation Example 6 19, 24, 25, 27, 29, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 49, 50, 51, 52 or 53 so that the concentration is 200 ppm. The mixture was sprayed on the foliage so that the mixture was well attached to the leaf surface of the wheat. After spraying, the wheat was air-dried and cultivated under light at 20 ° C.
  • 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.
  • Test Example 13 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 compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 formulated according to the method described in Formulation Example 6 , 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42 , 43, 45, 46, 48, 49, 50, 51, 52, 53 or 54 are mixed with water so that the concentration is 200 ppm, and the mixture is sprayed on the foliage so that it adheres well to the leaves of the soybean. did.
  • soybeans After spraying, the soybeans were air-dried, and 4 days later, a water suspension of soybean rust fungus (Phakopsora pachyrhizi) was spray-inoculated. After inoculation, soybeans were placed in a humid room at 23 ° C. in the daytime and at 20 ° C. for one day under high humidity, then cultivated in the greenhouse for 14 days, and then the lesion area was examined.
  • a water suspension of soybean rust fungus Phakopsora pachyrhizi
  • Test Example 14 Control Test against Soybean Rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, soybean (variety: 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.
  • the lesion area in the treated soybean was 30% or less of the lesion area in the untreated soybean.
  • Test Example 15 Control test against cucumber anthracnose (Colletotrichum lagenarium) A plastic pot was filled with soil, and cucumber (variety; Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 19 days.
  • the present compound 1, 2, 10, 14, 17, 19, 20, 24, 27, 28, 31, 33, 37, 38, 40 or 41 formulated according to the method described in Formulation Example 6
  • the mixture was mixed with water so as to be 200 ppm, and the mixture was sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the cucumber was air-dried, and one day later, an aqueous suspension of cucumber anthracnose fungus spores was spray-inoculated. After inoculation, it was first placed at 23 ° C.
  • Test Example 16 Control test against barley cloud disease (Rhynchosporium secalis) A plastic pot was stuffed with soil, seeded with barley (variety: Nishinohoshi), and grown in a greenhouse for 7 days.
  • the compound 26, 28, 35, 39 or 46 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 200 ppm, and the mixture is sufficiently applied to the leaves of the barley. The foliage was sprayed to adhere. After spraying, the barley was air-dried, and one day later, an aqueous suspension of barley cloud fungus spores was spray-inoculated. After inoculation, the barley was placed under humid conditions at 15 ° C. for 3 days, and then cultivated in a greenhouse for 14 days. As a result, the lesion area in the barley treated with the compound 26, 28, 35, 39 or 46 of the present invention was 30% or less of the lesion area in the untreated barley.
  • Test Example 17 Control test against cucumber downy mildew (Pseudoperonospora cubensis) A plastic pot was filled with soil, and cucumber (variety; Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 19 days.
  • the compound 14 of the present invention formulated according to the method described in Formulation Example 6 was mixed with water so as to have a concentration of 200 ppm, and the mixture was sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the cucumber was air-dried, and one day later, a water suspension of cucumber downy mildew spores was spray-inoculated. After inoculation, it was first placed at 23 ° C.
  • the lesion area in the cucumber treated with the compound 14 of the present invention was 30% or less of the lesion area in the untreated cucumber.
  • Test Example 18 Control Test against Sclerotinia sclerotiorum
  • a plastic pot was filled with soil, and green beans (variety; Nagatake peas) were sown there and allowed to grow in a greenhouse for 8 days.
  • the compound 8 of the present invention formulated in accordance with the method described in Formulation Example 6 was mixed with water to a concentration of 500 ppm, and the mixture was sprayed on the foliage so that the mixture was sufficiently attached to the kidney leaf surface. After spraying, the kidney beans were air-dried and a mycelia-containing PDA medium of kidney bean sclerotia was placed on the leaf surface of kidney beans.
  • the lesion area in the kidney beans treated with Compound 8 of the present invention was 30% or less of the lesion area in the untreated kidney beans.
  • Test Example 19 Control test against cucumber powdery mildew (Sphaerotheca fuliginea) A plastic pot was filled with soil, and cucumber (cultivar; Sagamihanjiro) was sown therein and allowed to grow in a greenhouse for 12 days. Thereafter, the compound 25 or 46 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 500 ppm, and the mixture is sufficiently adhered to the leaf surface of the cucumber. The foliage was sprayed. After spraying, the cucumber was air-dried, placed in a greenhouse at 24 ° C. in the daytime and 20 ° C.
  • the lesion area in the cucumber treated with the compound 25 or 46 of the present invention was 30% or less of the lesion area in the untreated cucumber.
  • Reference test example 2 10% Color Coat Red aqueous solution (V / V) (Becker Underwood, Inc .: colorant) and 10% CF-Clear aqueous solution (V / V) (Becker Underwood, Inc .: binder) were mixed. A slurry solution was prepared. The compound 51 of the present invention formulated according to the method described in Formulation Example 6 is added to the resulting slurry solution, and the seed is coated on the corn so that 500 ⁇ g of the compound 51 of the present invention adheres per gram of corn seed. Treated. The treated corn was sown on a paper towel and cultivated at 27 ° C. for 3 days. Cultivated corn was wrapped in ice for 5 days (low temperature stress applied).
  • plant diseases can be controlled.

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

Abstract

La présente invention concerne un agent de lutte contre les maladies des plantes contenant un composé indiqué par la formule (I). [Dans la formule, G représente un noyau benzène, un noyau thiophène, un noyau furane, un noyau pyrazole, un noyau imidazole, un noyau oxazole, un noyau isoxazole, un noyau thiazole, un noyau oxadiazole, un noyau thiadiazole, un noyau pyridine, un noyau pyrazine, un noyau pyrimidine, un noyau pyridazine, ou analogue, A représente NR12, un atome d'oxygène ou un atome de soufre, R12 représente un groupe hydrocarbure à chaîne C1-C6 ou similaire pouvant présenter un ou plusieurs substituants choisis dans le groupe M, X représente un atome d'oxygène ou un atome de soufre, E représente NR300R301, et, de par l'atome d'azote lié à eux, R300 et R301 forment un groupe hétérocyclique non aromatique de 3 à 8 chaînons ou similaire.]
PCT/JP2016/088074 2015-12-25 2016-12-21 Agent de lutte contre les maladies des plantes contenant un compose oxadiazole Ceased WO2017110861A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2019003956A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Composé oxadiazole et utilisation associée
WO2019022061A1 (fr) 2017-07-27 2019-01-31 日本曹達株式会社 Composé oxadiazole et fongicide pour utilisation agricole et horticole
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
WO2019171234A1 (fr) 2018-03-09 2019-09-12 Pi Industries Ltd. Composés hétérocycliques en tant que fongicides
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2020208510A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte contre ou la prévention contre des champignons phytopathogènes
WO2020208511A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
WO2020208509A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
WO2020247504A1 (fr) 2019-06-06 2020-12-10 Aligos Therapeutics, Inc. Composés hétérocycliques
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
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
WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
CN116253727A (zh) * 2021-12-09 2023-06-13 浙江省化工研究院有限公司 一类含三氟甲基噁二唑连苯基的哌啶酰胺类化合物、其制备方法及应用
CN116253728A (zh) * 2021-12-09 2023-06-13 浙江省化工研究院有限公司 一类含三氟甲基噁二唑连噻吩的哌啶酰胺类化合物、其制备方法及应用
US11938134B2 (en) 2017-03-10 2024-03-26 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions
US12528767B2 (en) 2019-07-30 2026-01-20 Eikonizo Therapeutics, Inc. HDAC6 inhibitors and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63162680A (ja) * 1986-12-12 1988-07-06 チバーガイギー　アクチエンゲゼルシヤフト オキサジアゾール誘導体およびそれを含む有害生物防除剤組成物
JP2002114751A (ja) * 2000-08-04 2002-04-16 Aventis Cropscience Sa 殺菌性のフェニル（チオ）ウレア及びフェニル（チオ）カーバメートの誘導体
JP2002532497A (ja) * 1998-12-17 2002-10-02 アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング ４−トリフルオロメチル−３−オキサジアゾリルピリジン、その製造方法、その化合物を含有する薬剤、および農薬としてのその使用
JP2003535109A (ja) * 2000-06-08 2003-11-25 シンジエンタ パーテイスィペイシヨンズ アクチエンゲゼルシヤフト Ｎ−フェニル−（４−ピリジル）−２−ピリミジンアミン誘導体
JP2005520808A (ja) * 2002-01-17 2005-07-14 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺虫剤として使用される置換ピラゾリン
WO2015185485A1 (fr) * 2014-06-06 2015-12-10 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre des fongus phytopathogènes

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63162680A (ja) * 1986-12-12 1988-07-06 チバーガイギー　アクチエンゲゼルシヤフト オキサジアゾール誘導体およびそれを含む有害生物防除剤組成物
JP2002532497A (ja) * 1998-12-17 2002-10-02 アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング ４−トリフルオロメチル−３−オキサジアゾリルピリジン、その製造方法、その化合物を含有する薬剤、および農薬としてのその使用
JP2003535109A (ja) * 2000-06-08 2003-11-25 シンジエンタ パーテイスィペイシヨンズ アクチエンゲゼルシヤフト Ｎ−フェニル−（４−ピリジル）−２−ピリミジンアミン誘導体
JP2002114751A (ja) * 2000-08-04 2002-04-16 Aventis Cropscience Sa 殺菌性のフェニル（チオ）ウレア及びフェニル（チオ）カーバメートの誘導体
JP2005520808A (ja) * 2002-01-17 2005-07-14 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺虫剤として使用される置換ピラゾリン
WO2015185485A1 (fr) * 2014-06-06 2015-12-10 Basf Se Utilisation d'oxadiazoles substitués pour lutter contre des fongus phytopathogènes

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US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11180462B2 (en) 2015-10-02 2021-11-23 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11066375B2 (en) 2015-10-02 2021-07-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11259524B2 (en) 2016-01-08 2022-03-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US12370194B2 (en) 2017-03-10 2025-07-29 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US11938134B2 (en) 2017-03-10 2024-03-26 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions
WO2019003956A1 (fr) * 2017-06-27 2019-01-03 住友化学株式会社 Composé oxadiazole et utilisation associée
KR20200033256A (ko) 2017-07-27 2020-03-27 닛뽕소다 가부시키가이샤 옥사디아졸 화합물 및 농원예용 살균제
WO2019022061A1 (fr) 2017-07-27 2019-01-31 日本曹達株式会社 Composé oxadiazole et fongicide pour utilisation agricole et horticole
US11365193B2 (en) 2017-07-27 2022-06-21 Nippon Soda Co., Ltd. Oxadiazole compound and fungicide for agricultural and horticultural use
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
US11286242B2 (en) 2018-01-30 2022-03-29 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
WO2019171234A1 (fr) 2018-03-09 2019-09-12 Pi Industries Ltd. Composés hétérocycliques en tant que fongicides
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
WO2020208511A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
WO2020208509A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
WO2020208510A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte contre ou la prévention contre des champignons phytopathogènes
US12486240B2 (en) 2019-04-08 2025-12-02 Pi Industries Ltd. Oxadiazole compounds for controlling or preventing phytopathogenic fungi
EP3980406A4 (fr) * 2019-06-06 2023-06-28 Aligos Therapeutics, Inc. Composés hétérocycliques
WO2020247504A1 (fr) 2019-06-06 2020-12-10 Aligos Therapeutics, Inc. Composés hétérocycliques
US12528767B2 (en) 2019-07-30 2026-01-20 Eikonizo Therapeutics, Inc. HDAC6 inhibitors and uses thereof
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
WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
CN116253727A (zh) * 2021-12-09 2023-06-13 浙江省化工研究院有限公司 一类含三氟甲基噁二唑连苯基的哌啶酰胺类化合物、其制备方法及应用
CN116253728A (zh) * 2021-12-09 2023-06-13 浙江省化工研究院有限公司 一类含三氟甲基噁二唑连噻吩的哌啶酰胺类化合物、其制备方法及应用
CN116253728B (zh) * 2021-12-09 2025-07-04 浙江省化工研究院有限公司 一类含三氟甲基噁二唑连噻吩的哌啶酰胺类化合物、其制备方法及应用

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