WO2017110862A1 - Composé d'oxadiazole et son utilisation - Google Patents

Composé d'oxadiazole et son utilisation Download PDF

Info

Publication number
WO2017110862A1
WO2017110862A1 PCT/JP2016/088076 JP2016088076W WO2017110862A1 WO 2017110862 A1 WO2017110862 A1 WO 2017110862A1 JP 2016088076 W JP2016088076 W JP 2016088076W WO 2017110862 A1 WO2017110862 A1 WO 2017110862A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
ring
hch
compound
substituents selected
Prior art date
Application number
PCT/JP2016/088076
Other languages
English (en)
Japanese (ja)
Inventor
貞幸 有森
将起 山本
Original Assignee
住友化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Publication of WO2017110862A1 publication Critical patent/WO2017110862A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N47/20—N-Aryl derivatives 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
    • C07D413/10—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 carbon chain containing aromatic rings

Definitions

  • the present invention relates to an oxadiazole compound and its use.
  • 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 compound having an excellent control effect against plant diseases.
  • the present inventor has found that the compound represented by the following formula (1) has an excellent control effect against plant diseases. That is, the present invention is as follows. [1] Formula (1) [Where, G is a benzene ring, thiophene ring, furan 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, The thiophene ring, the furan ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyrazine ring, the pyrimidine ring, and the pyridazine ring (the benzene ring, The thiophene ring, the
  • a C1-C6 alkoxy group optionally having one or more substituents selected from group A, a C3-C6 alkenyl group optionally having one or more halogen atoms, or one or more halogen atoms Represents an optionally substituted C3-C6 alkynyl group, Q represents an oxygen atom or a sulfur atom, X is CR 2 R 3 R 4 , NR 5 R 6 , OR 7 , a C3-C6 cycloalkyl group optionally having one or more substituents selected from group C, one or more selected from group C A phenyl group which may have a substituent, or a 5- or 6-membered heteroaryl group which may have one or more substituents selected from group C; R 2 , R 3 and R 4 are each independently selected from a hydrogen atom, a halogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, and group A A C3-C6
  • R 1 and R 2 are bonded to each other to form a 5- or 6-membered ring (the ring may have one or more substituents selected from group C)
  • X is NR 5 R 6
  • R 1 and R 5 are bonded to each other to form a 5- or 6-membered ring (the ring may have one or more substituents selected from group C).
  • X is OR 7
  • R 1 and R 7 are bonded to each other to form a 5- or 6-membered ring (the ring may have one or more substituents selected from group C).
  • R 2 and R 3 may have one or more substituents selected from group C together with the carbon atom to which they are attached.
  • a 7-membered non-aromatic heterocyclic group may be formed
  • R 5 and R 6 may have one or more substituents selected from group C together with the nitrogen atom to which they are bonded.
  • a non-aromatic heterocyclic group may be formed.
  • Group A halogen atom, nitro group, cyano 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 A C3-C6 cycloalkyl group and a phenyl group which may have one or more halogen atoms (the phenyl group has a C1-C6 alkyl group which may have one or more halogen atoms or one or more halogen atoms). And optionally having a C1-C6 alkoxy group).
  • Group B A group consisting of a halogen atom, a nitro group, and a cyano group.
  • Group C a C1-C6 alkyl group optionally having one or more substituents selected from Group B, a C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms
  • An oxadiazole compound represented by the following hereinafter referred to as the present compound).
  • G is a benzene ring optionally having one or more substituents selected from group C.
  • G is a benzene ring
  • Q is an oxygen atom
  • X is CR 2 R 3 R 4
  • R 1 and R 2 are bonded to each other to form a 5- or 6-membered ring
  • R 3 and R 4 are each independently a hydrogen atom or C1-C6
  • An alkyl group or X is NR 5 R 6 , and R 1 and R 5 are bonded to each other to form a 5- or 6-membered ring
  • R 6 is selected from the group consisting of a halogen atom and a C3-C6 cycloalkyl group
  • X is OR 7 , and R 1 and R 7 are bonded to each other to form 5 or 6 Forming a member ring,
  • X is CR 2 R 3 R 4 and R 1 and R 2 are bonded to each other to form a 5- or 6-membered ring, and R 3 and R 4 are hydrogen atoms
  • X is NR 5 R 6
  • R 1 and R 5 are bonded to each other to form a 5- or 6-membered ring
  • R 6 may have one or more halogen atoms, a C1-C6 alkyl group, A hydrogen atom, a C3-C6 alkynyl group, or a cyclopropylmethyl group
  • X is OR 7 , and R 1 and R 7 are bonded to each other to form a 5- or 6-membered ring, [3 ] The compound as described in this.
  • a plant disease control agent containing an oxadiazole compound represented by the formula (1) (hereinafter referred to as the present invention control agent).
  • a composition containing more than a seed is selected from the group consisting of an oxadiazole compound represented by the formula (1), and insecticides, acaricides, nematocides, plant growth regulators, synergists and other plant disease control agents.
  • plant diseases can be controlled.
  • halogen atoms when two or more halogen atoms are present, these halogen atoms may be the same or different from each other.
  • Cn—Cm means that the number of carbon atoms is n to m.
  • C1-C6 means 1 to 6 carbon atoms.
  • 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.
  • the “5- or 6-membered heteroaryl group” means a 5-membered heteroaryl group or a 6-membered heteroaryl group, and the 5-membered heteroaryl group is a pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, triazolyl group.
  • “3-7-membered non-aromatic heterocyclic group” means an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine Ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, 1,4-thiazepane ring, etc. To express.
  • R 1 and R 2 may be bonded to each other to form a 5- or 6-membered ring.
  • the ring include the following rings ( ⁇ represents a binding site with G).
  • R 1 and R 5 may be bonded to each other to form a 5- or 6-membered ring.
  • examples of the ring include the following rings ( ⁇ represents a binding site with G).
  • OR 7 R 1 and R 7 may be bonded to each other to form a 5- or 6-membered ring.
  • the ring include the following rings ( ⁇ represents a binding site with G).
  • the compound of the present invention may have one or more stereoisomers.
  • Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • the present invention includes each stereoisomer and any ratio of stereoisomer mixtures.
  • the compound of the present invention is mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • Examples of the compound of the present invention include the following.
  • G is a benzene ring
  • R 1 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • X is CR 2 R 3 R 4 , NR 5 R 6 , OR 7 or a phenyl group which may have one or more substituents selected from group C
  • R 2 , R 3 and R 4 are each independently selected from a hydrogen atom, a halogen atom and group A
  • a C1-C6 chain hydrocarbon group which may have one or more substituents, or a C3-C6 cycloalkyl group which may have one or more substituents selected from group A
  • R 5 And R 6 each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, or one or more substituents selected from group A.
  • a C3-C6 cycloalkyl group optionally having, When X is CR 2 R 3 R 4 , R 1 and R 2 are bonded to each other to form a 5- or 6-membered ring (the ring may have one or more substituents selected from group C) ) When X is OR 7 , R 1 and R 7 are bonded to each other to form a 5- or 6-membered ring (the ring may have one or more substituents selected from group C).
  • G is a benzene ring, thiophene ring, furan ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyrimidine ring or pyridazine ring (this The benzene ring, the thiophene ring, the furan ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyrazine ring, the pyrimidine ring, and the pyridazine ring are selected from group C 1 R 1 is a C1-C6 alkyl group which may have one or more halogen atoms, and X is CR 2 R 3 R 4 ,
  • G is a benzene ring
  • Q is an oxygen atom
  • X is CR 2 R 3 R 4
  • R 1 and R 2 are bonded to each other to form a pyrrolidinone ring or piperidinone ring (provided that the pyrrolidinone ring and piperidinone ring may have one or more halogen atoms).
  • R 3 and R 4 are each independently a hydrogen atom or a C1-C6 alkyl group, A compound in which N (R 1 ) C (Q) X is bonded to the oxadiazole ring at the para position on the benzene ring.
  • G is a benzene ring
  • Q is an oxygen atom
  • X is CR 2 R 3 R 4
  • R 1 and R 2 are bonded to each other to form a pyrrolidinone ring or piperidinone ring
  • R 3 and R 4 are hydrogen atoms
  • a compound in which N (R 1 ) C (Q) X is bonded to the oxadiazole ring at the para position on the benzene ring.
  • G is a benzene ring
  • Q is an oxygen atom
  • X is NR 5 R 6
  • R 1 and R 5 are bonded to each other to form an imidazolidinone ring or a tetrahydropyrimidinone ring
  • R 6 is a C1-C6 chain hydrocarbon group or hydrogen atom which may have one or more substituents selected from the group consisting of a halogen atom, a phenyl group and a C3-C6 cycloalkyl group
  • a compound in which N (R 1 ) C (Q) X is bonded to the oxadiazole ring at the para position on the benzene ring.
  • G is a benzene ring
  • Q is an oxygen atom
  • X is OR 7
  • R 1 and R 7 are bonded to each other to form an oxazolidinone ring or an oxazinan-2-one ring.
  • N (R 1 ) C (Q) X is bonded to the oxadiazole ring at the para position on the benzene ring.
  • control agent The following are mentioned as an aspect of this invention control agent.
  • G is a benzene ring
  • R 1 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • X is CR 2 R 3 R 4 , NR 5 R 6 , OR 7 or a phenyl group optionally having one or more substituents selected from group C
  • R 2 , R 3 and R 4 are each independently selected from a hydrogen atom, a halogen atom and group A
  • a C1-C6 chain hydrocarbon group optionally having one or more substituents
  • R 5 and R 6 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, or one or more substituents selected from group A A C3-C6 cycloalkyl group optionally having
  • R 5 and R 6 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, or one or more substituents selected from group
  • the compound of the present invention can be produced, for example, by the following production method.
  • the compound of the present invention comprises 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)) in the presence of a base. It can manufacture by making it react. [Wherein, Xa represents a halogen atom, and G, R 1 , Q and X have the same meaning as defined in [1]. ] The reaction is usually performed in a solvent.
  • hydrocarbons such as hexane, cyclohexane, toluene and xylene (hereinafter referred to as hydrocarbons), diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert.
  • ethers such as butyl ether and diisopropyl ether (hereinafter referred to as ethers), halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene (hereinafter referred to as halogenated hydrocarbons), dimethylformamide, 1, 3 -Acid amides such as 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), dimethyl sulfoxide Such as sulfoxides (hereinafter referred to as Nitrides such as acetonitrile and propionitrile (hereinafter referred to as nitriles), alcohols such as methanol, ethanol, propanol and butanol (hereinafter referred to as alcohols), water, and these Of the mixture.
  • ethers such as butyl ether and diis
  • 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), and carbonates such as sodium carbonate and potassium carbonate.
  • organic bases such as triethylamine, pyridine, 2,2′-bipyridine, diazabicycloundecene (hereinafter referred to as organic bases)
  • carbonates sodium hydrogen carbonate
  • potassium hydrogen carbonate hereinafter referred to as hydrogen carbonates
  • metal hydrides such as sodium hydride, potassium hydride, lithium hydride (hereinafter referred to as hydrogenation).
  • metals metals
  • compound (A2) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (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 of the present invention can be isolated by performing post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, and drying and concentrating the organic layer.
  • a compound represented by formula (1A) (hereinafter referred to as compound (1A)) is represented by a compound represented by formula (A3) (hereinafter referred to as compound (A3)) and formula (A5-1). It can be produced by reacting a compound (hereinafter referred to as compound (A5-1)) in the presence of a base.
  • a compound represented by formula (A5-1) (wherein, Xb represents a halogen atom, G represents the same meaning as defined in [1], n and X 1 represent the same meaning as defined in Embodiment 7, and Xa represents the same meaning as defined in Production Method A. To express. ]
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
  • Examples of the base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • compound (A5-1) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (A3).
  • 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 (1A) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • compound (1A) can be produced by ring-closing a compound represented by formula (A4) (hereinafter referred to as compound (A4)) in the presence of a base.
  • A4 a compound represented by formula (A4)
  • G represents the same meaning as defined in [1]
  • n and X 1 represent the same meaning as defined in Embodiment 7, and
  • Xb represents the same meaning as defined in Production Method B.
  • 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 base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • the base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (A4).
  • 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 (1A) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • Compound (A4) is known or can be produced according to a known method (for example, Bioorganic & Medicinal Chemistry, 2012, 20, 3575).
  • a compound represented by formula (1A-4) (hereinafter referred to as compound (1A-4)) is a compound represented by formula (A111) (hereinafter referred to as compound (A111)) and trifluoroacetic anhydride. (Hereinafter referred to as the compound (A7)) in the presence of a base.
  • G, R 1 and X have the same meanings as defined in [1].
  • the reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
  • Examples of the base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • compound (A7) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (A111).
  • 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 (1A-4) can be isolated by performing post-treatment operations such as mixing of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • a compound represented by formula (1A-3) (hereinafter referred to as compound (1A-3)) is a compound represented by formula (1A-2) (hereinafter referred to as compound (1A-2)) and a formula. It can be produced by reacting a compound represented by (A2-1) (hereinafter referred to as compound (A2-1)) in the presence of a base.
  • a compound represented by (A2-1) hereinafter referred to as compound (A2-1)
  • n represents the same meaning as defined in Embodiment 7
  • Xa represents the same meaning as defined in Production Method A.
  • the reaction is carried out according to the method described in Production Method A.
  • Compound (1A-2) can be produced according to the method described in Production Method A.
  • Reference manufacturing method A Compound (A1) can be produced by reacting compound (A3) with a compound represented by formula (A5-2) (hereinafter referred to as compound (A5-2)) in the presence of a base.
  • A5-2 a compound represented by formula (A5-2)
  • 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 base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • compound (A5-2) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (A3).
  • 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 (A1) 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.
  • Reference manufacturing method B Compound (A3) can be produced by reacting a compound represented by formula (A6) (hereinafter referred to as compound (A6)) with compound (A7) in the presence of a base.
  • a compound represented by formula (A6) hereinafter referred to as compound (A6)
  • compound (A7) in the presence of a base.
  • G represents the same meaning as defined in [1].
  • 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 base used in the reaction include organic bases, carbonates, hydrogen carbonates, and metal hydrides.
  • compound (A7) is usually used in a proportion of 1 to 10 mol and base is used in a proportion of 1 to 10 mol with respect to 1 mol of compound (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 (A3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with water and extraction with an organic solvent, and drying and concentration of the organic layer.
  • Compound (A6) is publicly known or can be produced according to a known method (for example, Patent Document 1).
  • Reference manufacturing method C Compound (A111) can be produced by reacting a compound represented by formula (A112) (hereinafter referred to as compound (A112)) with hydroxylamine. Wherein, G, R 1 and X have the same meanings as defined in [1]. ] The reaction is carried out according to a known method (for example, International Publication No. 2009/081891).
  • Reference manufacturing method D Compound (A112) can be produced by reacting a compound represented by formula (A113) (hereinafter referred to as compound (A113)) with compound (A2). [Wherein G, R 1 and X represent the same meaning as defined in [1], and Xa represents the same meaning as defined in Production Method A. ] The reaction is carried out according to the method described in Production Method A.
  • the compound represented by the formula (A112-1) (hereinafter referred to as the compound (A112-1)) is the base represented by the compound represented by the formula (A113-1) (hereinafter referred to as the compound (A113-1)).
  • A113-1 the base represented by the compound represented by the formula (A113-1) (hereinafter referred to as the compound (A113-1)).
  • G represents the same meaning as defined in [1]
  • n and X 1 represent the same meaning as defined in Embodiment 7
  • Xb represents the same meaning as defined in Production Method B.
  • the reaction is carried out according to the method described in Production Method C.
  • Compound (A113-1) is known or can be produced according to a known method (for example, Bioorganic & Medicinal Chemistry, 2012, 20, 3575).
  • Compound (A113) is a reaction of a compound represented by Formula (A114) (hereinafter referred to as Compound (A114)) with a compound represented by Formula (A5) (hereinafter referred to as Compound (A5)).
  • Compound (A5) a compound represented by Formula (A5)
  • G and X represent the same meaning as defined in [1]
  • Xa represents the same meaning as defined in Production Method A.
  • the reaction is known or carried out according to a known method (for example, Bioorganic & Medicinal Chemistry, 2012, 20, 3575).
  • Compound (A114) is known.
  • Reference manufacturing method G Compound (A1) can be produced by reacting a compound represented by the formula (A115) (hereinafter referred to as compound (A115)) with compound (A5-2) in the presence of a base.
  • a compound represented by the formula (A115) hereinafter referred to as compound (A115)
  • compound (A5-2) in the presence of a base.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, acid amides, esters, sulfoxides, nitriles, alcohols, water, and mixtures thereof.
  • the base used in the reaction include organic bases, carbonates, bicarbonates, and metal hydrides.
  • Compound (A115) may be in the form of a salt.
  • the salt of compound (A115) include hydrochloride and sulfate.
  • compound (A5-2) is usually used at a ratio of 1 to 10 mol
  • base is usually used at a ratio of 1 to 20 mol.
  • the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 120 hours.
  • the compound (A1) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (A115) is known or can be produced according to a known method (for example, International Publication No. 2016/031815).
  • 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 form of the compound of the present invention may be the compound of the present invention alone.
  • the compound of the present invention is mixed with a solid carrier, a liquid carrier, a surfactant, etc., and if necessary, a fixing agent or a dispersing agent.
  • Additives for preparations such as stabilizers, wettable powder, granular wettable powder, flowable, granule, dry flowable, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule It is used by formulating it.
  • These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
  • the solid support examples include clays (for example, kaolin, diatomaceous earth, fubasami clay, bentonite, acid clay), synthetic hydrous silicon oxide, talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples thereof include fine powders such as calcium carbonate) and granular materials.
  • clays for example, kaolin, diatomaceous earth, fubasami clay, bentonite, acid clay
  • synthetic hydrous silicon oxide for example, sericite, quartz powder, sulfur powder, activated carbon
  • examples thereof include fine powders such as calcium carbonate
  • liquid carrier examples include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (For example, 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 Formula example, 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 (Erysiphe) graminis), red mold (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P.
  • 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
  • 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.
  • Noctuidae such as vine borer (Hydraecia immanis); Pieridae, such as Pieris rapae; Grapholita molesta, Grapholita dimorpha, glycine Matsumuraeses azukivora, Adoxophyes orana fasciata, Chanocok's leaflet (Adoxophyes honmai), Chamonaki (Homona magnanima), Midarekamon leaflet (Archips fuscocupreanus), Kodlinga ella, Mocha schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana) and other species of Tortricidae; Caloptilia ⁇ theivora; Carposin e (Carposina sasakii), etc.
  • Carposinidae Coffee Leaf miner (Leucoptera coffeela), 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; Plutellidae such as Plumellidae; Species of Helicodiae (Helcystogramma triannulellum), Cotton moth (Pectinophora gossypiella), Potato moth (Phthorimaea operculella), Tuta absoluta, etc. 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 Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), tiger beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), pheasant horn beetle (Phyllotretatlebetreta black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryza
  • Carabidae Carabidae; ), Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), Black marsh (Tomarus gibbosus), Holotrichia (Holotrichia s) Phyllophaga genus (Phyllophaga spp.) Such as Phyllophaga crinita), Scarabaeidae such as Diloboderus spp.
  • Tribolium castaneum, Tribolium confusum, etc . Tribolium castaneum, Tribolium confusum, etc .; Tenebrionidae; Epilachna vigintioctopunctata, etc .; Bostrychidae; Leopardidae (Ptinidae); Anoplophora malasiaca, Migdolus fryanus, etc. collis), Menotus legatus, Ashitus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus ppspp. Elateridae such as; 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 antaceae such as Athalia rosae and Athalia japonica; Tenthredinidae; fire ant (Solenopsis spp.) (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 compound of the present invention produced according to the method described in Production Example 1-1 and the physical properties thereof are shown below.
  • Production Example 2-2 The compound 8 of the present invention shown below was produced according to the method described in Production Example 2-1.
  • Compound 8 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.16-8.12 (2H, m), 7.56-7.53 (2H, m), 4.46 (2H, t), 3.81 (2H, t), 2.29-2.23 (2H, m).
  • Production Example 3-2 The compound 10 of the present invention shown below was produced according to the method described in Production Example 3-1.
  • Compound 10 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.64-7.67 (2H, m), 7.40-7.43 (2H, m), 3.68 (2H, t), 2.58 (2H, t), 1.91-2.01 (4H, m).
  • Production Example 5-1 A mixture of 0.4 g of the compound 11 of the present invention described in Production Example 4-1 and 4 mL of dimethylformamide was cooled to 0 ° C., 0.06 g of sodium hydride (60%, mineral oil dispersion) was added, and then at room temperature. Stir for 0.5 hour. The reaction mixture was cooled to 0 ° C. and 0.5 g of methyl iodide was added. After stirring the reaction mixture for 10 hours at room temperature, 10 mL of water was added. After extraction with ethyl acetate, the organic layer was dried and concentrated under reduced pressure.
  • sodium hydride 50%, mineral oil dispersion
  • Production Example 5-2 The compound of the present invention produced according to the method described in Production Example 5-1 and the physical properties thereof are shown below.
  • Production Example 7-1 The compound of the present invention produced according to the method described in Production Example 5-1, and the physical properties thereof are shown in the following formula (1c) Wherein R 6 is any one of the substituents described in [Table 3].
  • Reference production example 4 A mixture of 6.3 g of 4- (2-oxo-1-imidazolidinyl) benzenecarbonitrile, 100 mL of ethanol, and 8.4 mL of 50% -hydroxylamine aqueous solution was stirred under reflux for 8 hours. After cooling to room temperature, the resulting precipitate was collected by filtration, washed with ethanol, and dried under reduced pressure to obtain 7.1 g of intermediate (A15) shown below.
  • H represents a hydrogen atom
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • i-Pr represents an isopropyl group
  • c-Pr represents a cyclopropyl group.
  • Bu represents a butyl group
  • t-Bu represents a tert-butyl group
  • OMe represents a methoxy group
  • OEt represents an ethoxy group
  • Ph represents a phenyl group
  • Bn represents a benzyl group.
  • substituted a compound in which the combination of R 1 , R 21 , R 22 and R 23 is a combination described in any one of the substituent numbers RA1 to RA1376 shown below (hereinafter referred to as substituted)
  • the compounds of the group numbers RA1 to RA1376 are represented as compounds of the present invention RA1 to RA1376, respectively, and the compounds of the present invention RA1 to RA1376 are collectively represented as the compound of the present invention RA), and can be obtained according to the method described in the above production method it can.
  • the substituent number RA4 represents a combination in which R 1 is a methyl group, R 21 and R 22 are hydrogen atoms, and R 23 is an isopropyl group.
  • the compound RA4 of the present invention means a compound whose substituent number is RA4, and in the compound represented by the formula (III), R 1 is a methyl group, R 21 and R 22 are hydrogen atoms, R 23 represents a compound having an isopropyl group.
  • substitution a compound in which the combination of n, R 21 , R 22 and R 24 is a combination described in any one of the substituent numbers RB1 to RB158 shown below (hereinafter referred to as substitution)
  • the compounds of the group numbers RB1 to RB158 are represented as the present compounds RB1 to RB158, respectively, and the present compounds RB1 to RB158 are collectively represented as the present compound RB), which can be obtained according to the method described in the above production method. it can.
  • the substituent numbers RB1 to RB158 represent combinations of n, R 21 , R 22 and R 24 in the compound represented by the formula (IV). 21 , R 22 , R 24 ].
  • the substituent number RB4 represents a combination in which n is 1, R 21 and R 22 are hydrogen atoms, and R 24 is MeCH.
  • the compound RB4 of the present invention means a compound whose substituent number is RB4, and in the compound represented by the formula (IV), n is 1, R 21 and R 22 are hydrogen atoms, R 24 Represents a compound in which is CH.
  • the compound RA of the present invention and the compound RB of the present invention are referred to as the present compound A.
  • 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.
  • plant disease control agents such as 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 this component is not particularly limited, but is 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 1 in weight ratio (the compound of the present invention: this component).
  • Formulation Example 1 A formulation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds A of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide.
  • Formulation Example 2 20 parts of any one of the compounds A of the present invention 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 pulverization method. Thereafter, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, 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 any one of the compounds A of the present invention, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the compounds A of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 2 parts of any one of the compounds A of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, and then kneaded with water. The preparation is obtained by combining and granulating and drying.
  • Formulation Example 6 20 parts of any one compound of the present compound A; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make a total amount of 100 parts, and pulverized The preparation is obtained by processing using a machine.
  • test examples are shown.
  • the untreated section in Test Example 1 or Test Example 2 was performed under the same conditions as described in each test example except that dimethyl sulfoxide was dispensed instead of the dimethyl sulfoxide diluting solution containing the compound of the present invention. Represents a test zone.
  • the term “no treatment” in Test Example 3 to Test Example 9 indicates that the mixture of the preparation containing the compound of the present invention and water was not sprayed.
  • Test Example 1 Control test against tomato leaf mold (Cladosporium fulvum)
  • the present compound 1, 2, 7, 9, 17, 20 or 22 was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and 1 ⁇ L in a titer plate (96 well).
  • the spores of tomato leaf mold QoI resistant strain whose base sequence was mutated so that the 129th amino acid residue of cytochrome b was replaced with phenylalanine from leucine among the genes encoding cytochrome b
  • 150 ⁇ L of the inoculated potato broth liquid medium (PDB medium) was dispensed. This plate was cultured at 18 ° C.
  • the growth degree in the section treated with the present compound 1, 2, 7, 9, 17, 20, or 22 was 40% or less of the growth degree in the untreated section.
  • Test Example 2 Control test against wheat leaf blight fungus (Septoria tritici)
  • the present compound 1, 2, 3, 4, 6, 7, 8, 9, 10, 11 or 12 was diluted with dimethyl sulfoxide so as to contain 1500 ppm, After 1 ⁇ L was dispensed into a titer plate (96 well), 150 ⁇ L of a potato broth liquid medium (PDB medium) previously inoculated with spores of wheat leaf blight fungus was dispensed. This plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight fungi. Then, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of wheat leaf blight fungi. As a result, the growth in the group treated with the compound 1, 2, 3, 4, 6, 7, 8, 9, 10, 11 or 12 of the present invention was 40% or less of the growth in the untreated group. It was.
  • PDB medium potato broth liquid medium
  • Test Example 3 Control Test for Soybean Rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown there, grown in a greenhouse for 10 days, and an aqueous suspension of soybean rust fungus spores. Was spray-inoculated. After inoculation, the present compound 1 was formulated according to the method described in Formulation Example 6 after placing soybeans in a humid room at 23 ° C. in the daytime and 20 ° C. for 1 day in a humid room and then cultivating in the greenhouse for 2 days.
  • Test Example 4 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and soybean (cultivar; Kurosengoku) was sown therein and allowed to grow in a greenhouse for 13 days.
  • the present compound 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19 formulated according to the method described in Formulation Example 6 , 20, 21 or 22 was mixed with water to a concentration of 200 ppm, and the mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the soybean. After spraying, the soybeans were air-dried, and after 4 days, sprayed with a water suspension of soybean rust spores. After inoculation, soybeans were placed in a humid room at 23 ° C.
  • soybeans treated with the compounds 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21 or 22 of the present invention were treated with the compounds 1, 2, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21 or 22 of the present invention.
  • the lesion area was 30% or less of the lesion area in untreated soybean.
  • Test Example 5 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days.
  • the compound 6, 7, 13 or 16 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 500 ppm, and the mixture adheres sufficiently to the leaf surface of the rice. So that the foliage was sprayed. 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 present compound 6, 7, 13 or 16 was 30% or less of the lesion area in untreated rice.
  • Test Example 6 Control Trial against Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and then wheat (cultivar: Apogee) was sown therein and cultivated in a greenhouse for 10 days.
  • the compound of the present invention 2, 7, 8, 9, 10, 11, 13, 14, 15, 18, 19, 20, 21, or 22 formulated according to the method described in Formulation Example 6 has a concentration of 500 ppm. Then, the mixture was sprayed with foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried, and after 4 days, a water suspension containing spores of wheat leaf blight was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C.
  • the lesion areas in the wheat treated with the compound 2, 7, 8, 9, 10, 11, 13, 14, 15, 18, 19, 20, 21 or 22 of the present invention are all in the untreated wheat. It was 30% or less of the lesion area.
  • Test Example 7 Control Trial against Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and then wheat (cultivar: Apogee) was sown therein and cultivated in a greenhouse for 10 days.
  • the compound 2, 6, 10, 11, 13, 14 or 17 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 mixed with the above wheat The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the wheat was air-dried, and after 4 days, a water suspension containing spores of wheat leaf blight was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C.
  • the lesion area in the wheat treated with the compound 2, 6, 10, 11, 13, 14 or 17 of the present invention was 30% or less of the lesion area in the untreated wheat.
  • Test Example 8 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, sowed with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days.
  • the present compound 2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 17, 20, 21, or 22 formulated according to the method described in Formulation Example 6 has a concentration of 500 ppm. Then, the mixture was sprayed with foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried and cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus. After inoculation, the wheat was placed in a dark and humid environment at 23 ° C.
  • the lesion area in the wheat treated with the compound 2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 17, 20, 21 or 22 of the present invention was not treated. It was 30% or less of the lesion area in wheat.
  • Test Example 9 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, seeded with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days.
  • the compound 2, 8, 9, 10, 11 or 17 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 added to the leaf surface of the wheat. The foliage was sprayed so as to adhere well. 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. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination. As a result, the lesion area in the wheat treated with the compound 2, 8, 9, 10, 11 or 17 of the present invention was 30% or less of the lesion area in the untreated wheat.
  • the compound of the present invention has a controlling effect against plant diseases and is useful as an active ingredient of a plant disease controlling agent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Toxicology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Le composé d'oxadiazole représenté dans la formule (1) se révèle très efficace dans le cadre de la lutte contre les maladies des plantes. Dans la formule, G représente un noyau benzène, un noyau thiophène, un noyau furane, etc., R1 représente un groupe alkyle en C1-C6, un groupe cycloalkyle en C3-C6, etc., Q représente un atome d'oxygène ou un atome de soufre, X représente CR2R3R4, NR5R6, OR7, etc., R2, R3 et R4 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, etc., R5, R6 et R7 représentent chacun indépendamment un atome d'hydrogène, un groupe hydrocarboné à chaîne en C1-C6, etc.
PCT/JP2016/088076 2015-12-25 2016-12-21 Composé d'oxadiazole et son utilisation WO2017110862A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2015253228 2015-12-25
JP2015-253228 2015-12-25
JP2016190828 2016-09-29
JP2016-190828 2016-09-29

Publications (1)

Publication Number Publication Date
WO2017110862A1 true WO2017110862A1 (fr) 2017-06-29

Family

ID=59089439

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/088076 WO2017110862A1 (fr) 2015-12-25 2016-12-21 Composé d'oxadiazole et son utilisation

Country Status (1)

Country Link
WO (1) WO2017110862A1 (fr)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180362515A1 (en) * 2015-12-02 2018-12-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
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
US20190185462A1 (en) * 2016-06-23 2019-06-20 Merck Sharp & Dohme Corp. 3-aryl- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histonedeacetylase 6 (hdac6) inhibitors
WO2019122323A1 (fr) 2017-12-22 2019-06-27 Bayer Aktiengesellschaft Oxadiazoles fongicides
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
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
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
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
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
WO2020254494A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Oxadiazoles fongicides
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
WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022129190A1 (fr) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
WO2022249074A1 (fr) 2021-05-26 2022-12-01 Pi Industries Ltd. Composition fongicide contenant des composés oxadiazoles
WO2023286855A1 (fr) 2021-07-15 2023-01-19 クミアイ化学工業株式会社 Dérivé de formamide et agent de lutte contre les maladies des plantes agricoles ou horticoles
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

Citations (5)

* 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
WO1997030047A1 (fr) * 1996-02-17 1997-08-21 Agrevo Uk Limited 1,2,4 oxadiazoles fongicides et analogues
WO1998025912A1 (fr) * 1996-12-13 1998-06-18 E.I. Du Pont De Nemours And Company Amides heterocycliques herbicides
JPH11512423A (ja) * 1995-09-16 1999-10-26 アグレボ・ユー・ケイ・リミテツド 殺真菌剤としての置換された安息香酸アニリドまたはチオ安息香酸アニリド
WO2009133861A1 (fr) * 2008-04-28 2009-11-05 武田薬品工業株式会社 Composé amine cyclique

Patent Citations (5)

* 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
JPH11512423A (ja) * 1995-09-16 1999-10-26 アグレボ・ユー・ケイ・リミテツド 殺真菌剤としての置換された安息香酸アニリドまたはチオ安息香酸アニリド
WO1997030047A1 (fr) * 1996-02-17 1997-08-21 Agrevo Uk Limited 1,2,4 oxadiazoles fongicides et analogues
WO1998025912A1 (fr) * 1996-12-13 1998-06-18 E.I. Du Pont De Nemours And Company Amides heterocycliques herbicides
WO2009133861A1 (fr) * 2008-04-28 2009-11-05 武田薬品工業株式会社 Composé amine cyclique

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11066375B2 (en) 2015-10-02 2021-07-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11180462B2 (en) 2015-10-02 2021-11-23 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US20180362515A1 (en) * 2015-12-02 2018-12-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
JP2019506364A (ja) * 2015-12-02 2019-03-07 シンジェンタ パーティシペーションズ アーゲー 殺微生物性オキサジアゾール誘導体
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
US11066396B2 (en) * 2016-06-23 2021-07-20 Merck Sharp & Dohme Corp. 3-aryl- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histonedeacetylase 6 (HDAC6) inhibitors
US20190185462A1 (en) * 2016-06-23 2019-06-20 Merck Sharp & Dohme Corp. 3-aryl- heteroaryl substituted 5-trifluoromethyl oxadiazoles as histonedeacetylase 6 (hdac6) inhibitors
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
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
US11365193B2 (en) 2017-07-27 2022-06-21 Nippon Soda Co., Ltd. Oxadiazole compound and fungicide for agricultural and horticultural use
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
EP3660007A4 (fr) * 2017-07-27 2021-01-13 Nippon Soda Co., Ltd. Composé oxadiazole et fongicide pour utilisation agricole et horticole
US11266147B2 (en) 2017-12-22 2022-03-08 Bayer Aktiengesellschaft Fungicidal oxadiazoles
CN111683944A (zh) * 2017-12-22 2020-09-18 拜耳股份公司 杀真菌的噁二唑类
WO2019122323A1 (fr) 2017-12-22 2019-06-27 Bayer Aktiengesellschaft Oxadiazoles fongicides
US11286242B2 (en) 2018-01-30 2022-03-29 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
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
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
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
WO2020254494A1 (fr) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Oxadiazoles fongicides
WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022129190A1 (fr) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
WO2022249074A1 (fr) 2021-05-26 2022-12-01 Pi Industries Ltd. Composition fongicide contenant des composés oxadiazoles
WO2023286855A1 (fr) 2021-07-15 2023-01-19 クミアイ化学工業株式会社 Dérivé de formamide et agent de lutte contre les maladies des plantes agricoles ou horticoles

Similar Documents

Publication Publication Date Title
WO2017110862A1 (fr) Composé d&#39;oxadiazole et son utilisation
WO2018117034A1 (fr) Composé oxadiazole et procédé de lutte contre des maladies des plantes
RU2734971C2 (ru) Соединение пиразина и содержащее его средство для борьбы с членистоногими вредителями
WO2017111152A1 (fr) Composés oxadiazole et leur utilisation
WO2017110861A1 (fr) Agent de lutte contre les maladies des plantes contenant un compose oxadiazole
JP6914322B2 (ja) オキサジアゾール化合物及び農薬としてのその用途
EP3483144B1 (fr) Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant
WO2017213252A1 (fr) Composé d&#39;oxadiazole et son utilisation comme pesticide
WO2017169893A1 (fr) Composé oxadiazole et utilisation associée
CN113412050A (zh) 杂环化合物和含有该杂环化合物的有害节肢动物防除组合物
JP2019151553A (ja) オキサジアゾール化合物及びその用途
AU2018277980B2 (en) Heterocyclic compound and composition containing same
WO2017073733A1 (fr) Composition antiparasitaire et son utilisation
CA3145378A1 (fr) Derive d&#39;ester (meth)acrylique, et application et intermediaire de production de celui-ci
WO2021153786A1 (fr) Dérivé d&#39;acide phénylacétique, utilisation associée et intermédiaire de production associé
JP2019089711A (ja) オキサジアゾール化合物及びその用途
JP2017071604A (ja) 有害生物防除組成物およびその用途
WO2019003956A1 (fr) Composé oxadiazole et utilisation associée
WO2019124568A2 (fr) Composition et procédé de lutte contre les organismes nuisibles
WO2019083008A1 (fr) Composé pyridine, et composition de lutte contre des organismes nuisibles comprenant celui-ci
JP2017039751A (ja) 有害生物防除組成物およびその用途
JP2016222720A (ja) 有害生物防除組成物およびその用途
JP2017031193A (ja) 有害生物防除組成物およびその用途
JP2017043627A (ja) 有害生物防除組成物およびその用途

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16878749

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16878749

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP