WO2017111152A1 - Composés oxadiazole et leur utilisation - Google Patents

Composés oxadiazole et leur utilisation Download PDF

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Publication number
WO2017111152A1
WO2017111152A1 PCT/JP2016/088634 JP2016088634W WO2017111152A1 WO 2017111152 A1 WO2017111152 A1 WO 2017111152A1 JP 2016088634 W JP2016088634 W JP 2016088634W WO 2017111152 A1 WO2017111152 A1 WO 2017111152A1
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group
ring
substituents selected
optionally
compound
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PCT/JP2016/088634
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Japanese (ja)
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貞幸 有森
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住友化学株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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 represents a thiophene ring, furan ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring or 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, and the pyridazine ring have one or more substituents selected from group D
  • the pyrimidine ring may have one or more substituents selected from group A
  • the benzene ring may have one or more substituents selected from group E).
  • J represents CR 1 R 2 , NR 3 or an oxygen atom
  • Q is an oxygen atom, N—CN, N—NO 2 , N—C (O) R 4 or N—C (O) OR 4 (however, when n is 2, Q may be the same or different)
  • X is CR 5 R 6 R 7 , NR 8 R 9 , OR 10 , a C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, one or more selected from group D
  • m represents 0 or 1
  • n represents 0, 1 or 2
  • R 1 is a halogen atom, a C1-C6 alkyl group optionally having one or more substituents selected from group A, and a C1-C6 optionally having one or more substituents selected from group A.
  • R 2 may have a hydrogen atom, a halogen atom, a C1-C6 alkyl group which may have one or more substituents selected from group A, and one or more substituents selected from group A.
  • R 3 may have a hydrogen atom, a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A, and one or more substituents selected from group A.
  • R 4 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A or a hydrogen atom
  • R 5 , R 6 and R 7 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 C1-C6 alkoxy group optionally having one or more substituents, C3-C6 cycloalkyl group optionally having one or more substituents selected from group D, one or more selected from group D Or a 5- or 6-membered heteroaryl group optionally having one or more substituents selected from group D (provided that R 5 , R 6 and R When any one of 7 is a chlorine atom, any one of the remaining is a halogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group A, from group A C1-C6 alkoxy group optionally having one or more substituents
  • One or more oxazolyl groups optionally having at least one substituent selected from group D An isoxazolyl group which may have a substituent, a thiazolyl group which may have one or more substituents selected from group D, and an oxadiazolyl which may have one or more substituents selected from group D A group, a thiadiazolyl group optionally having one or more substituents selected from group D, a pyrazinyl group optionally having one or more substituents selected from group D, one or more selected from group D
  • R 1 and R 5 may be bonded to each other to form a 5- or 6-membered ring (the 5 or 6
  • the member ring may have one or more substituents selected from group D)
  • J is CR 1 R 2 and X is NR 8 R 9
  • R 1 and R 8 may be bonded to each other to form a 5- or 6-membered ring (the 5- or 6-membered ring).
  • R 1 and R 10 may be bonded to each other to form a 5- or 6-membered ring (the 5- or 6-membered ring is a group) One or more substituents selected from D may be present),
  • J is NR 3 and X is CR 5 R 6 R 7
  • R 3 and R 5 may be bonded to each other to form a 5- or 6-membered ring (the 5- or 6-membered ring).
  • R 3 and R 8 may be bonded to each other to form a 5- or 6-membered ring (the 5- or 6-membered ring is a group) One or more substituents selected from D may be present),
  • J is NR 3 and X is OR 10
  • R 3 and R 10 may be bonded to each other to form a 5- or 6-membered ring (the 5- or 6-membered ring is from group D).
  • R 5 When X is CR 5 R 6 R 7 , R 5 may be bonded to G to form a 5- or 6-membered ring (the 5- or 6-membered ring is one or more substituents selected from Group D) You may have) When X is NR 8 R 9 , R 8 may be bonded to G to form a 5- or 6-membered ring (the 5- or 6-membered ring has one or more substituents selected from Group D).
  • R 10 may be bonded to G to form a 5- or 6-membered ring (the 5- or 6-membered ring has one or more substituents selected from Group D) May be)
  • 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, and phenyl group (The phenyl group may have a C1-C6 alkyl group optionally having one or more halogen atoms or a C1-C6 alkoxy group optionally having one or more halogen atoms).
  • Group B a C2-C6 alkyl group optionally having one or more substituents selected from Group C, a C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms
  • Group C a group consisting of a halogen atom, a nitro group, and a cyano group.
  • Group D a C1-C6 alkyl group optionally having one or more substituents selected from Group C, a C1-C6 alkoxy group optionally having one or more halogen atoms, and one or more halogen atoms
  • Group E a C1-C6 alkyl group optionally having one or more substituents selected from group C, a C1-C6 alkylthio group optionally having one or more halogen atoms, a halogen atom, a cyano group, And a group consisting of a nitro group.
  • An oxadiazole compound represented by the formula: (Hereinafter referred to as the present compound).
  • G is a benzene ring optionally having one substituent selected from group D, a pyridine ring optionally having one substituent selected from group D, a substituent selected from group D A pyrimidine ring optionally having one or a pyridazine ring optionally having one substituent selected from group D;
  • Q is an oxygen atom or an N—CN group;
  • X is a C3-C6 cycloalkyl group optionally having one or more substituents selected from CR 5 R 6 R 7 or Group D;
  • m is 0;
  • R 5 , R 6 and R 7 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, or group D
  • G is a benzene ring optionally having one or more fluorine atoms;
  • Q is an oxygen atom or N-CN;
  • J is CR 1 R 2 or NR 3 ;
  • R 1 is a C1-C3 alkyl group;
  • R 2 is a hydrogen atom;
  • R 3 is a hydrogen atom or a C1-C3 chain hydrocarbon group;
  • X is CR 5 R 6 R 7 or a C3-C6 cycloalkyl group;
  • R 5 , R 6 and R 7 are each independently a hydrogen atom, a halogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
  • G is a benzene ring; m is 0; The oxadiazole compound according to [2] or [3], wherein X is CR 5 R 6 R 7 .
  • a plant disease control agent containing the oxadiazole compound according to [1] (hereinafter also referred to as the present control agent).
  • a plant disease control agent further comprising:
  • 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.
  • CW-CY means that the number of carbon atoms is W to Y.
  • 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.
  • “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.
  • a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group, and a 6-membered heteroaryl group represents a pyridyl group, a pyridazinyl group, a pyrimidinyl group, or a pyrazinyl group.
  • the 5- or 6-membered ring formed by bonding R 1 and R 5 to each other has the following structure of ZA1 or ZA2. ( ⁇ represents the binding position).
  • the 5- or 6-membered ring formed by bonding R 1 and R 8 to each other represents the following structure of ZB1 or ZB2 ( ⁇ represents the bonding position.
  • the 5- or 6-membered ring formed by bonding R 1 and R 10 to each other represents the following structure of ZC1 or ZC2 ( ⁇ indicates Represents the bond position).
  • the 5- or 6-membered ring formed by bonding R 3 and R 5 to each other represents the following structure of ZD1 or ZD2 ( ⁇ represents the bonding position.
  • the 5- or 6-membered ring formed by bonding R 3 and R 8 to each other represents the structure of ZE1 or ZE2 below ( ⁇ indicates Represents the bond position).
  • the 5- or 6-membered ring formed by bonding R 3 and R 10 to each other represents the structure of ZF1 or ZF2 below ( ⁇ is the bonding position) Represents).
  • the compound in which R 5 is bonded to G to form a 5- or 6-membered ring is any of the structures shown below (ZG1 to ZG8) ( ⁇ represents the binding position).
  • the compound in which R 8 is bonded to G to form a 5- or 6-membered ring represents any of the structures shown in the following (ZH1 to ZH8) ( ⁇ represents the bonding position.
  • 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 adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • Examples of the compound of the present invention include the following compounds.
  • G is a benzene ring
  • Q is an oxygen atom
  • m is 1
  • X is CR 5 R 6 R 7 , R 5 , R 6 , and R 7 are Each independently an oxadiazole compound which is a C1-C6 alkyl group optionally having one or more substituents selected from a hydrogen atom, a halogen atom or group A;
  • G is a benzene ring
  • Q is an oxygen atom
  • m is 1
  • n 2
  • J is NR 3
  • R 3 is a hydrogen atom, C 1- A C6 alkyl group or a C1-C6 alkoxy group
  • X is CR 5 R 6 R 7
  • R 5 , R 6 , and R 7 are each independently selected from a hydrogen atom, a halogen atom, or group
  • An oxadiazole compound which is a C1-C6 alkyl group which may have the above substituent.
  • G is a benzene ring
  • Q is an oxygen atom
  • m is 1
  • X is CR 5 R 6 R 7
  • R 5 , R 6 , and R 7 are An oxadiazole compound which is a C1-C6 chain hydrocarbon group which may each independently have one or more substituents selected from a hydrogen atom, a halogen atom or group A.
  • G is a benzene ring
  • Q is an oxygen atom
  • m is 1
  • n 2
  • J is NR 3
  • R 3 is a hydrogen atom, C 1- A C6 alkyl group or a C1-C6 alkoxy group
  • X is CR 5 R 6 R 7
  • R 5 , R 6 , and R 7 are each independently selected from a hydrogen atom, a halogen atom, or group
  • An oxadiazole compound which is a C1-C6 chain hydrocarbon group which may have the above substituents.
  • G is a benzene ring optionally having one or more fluorine atoms
  • Q is an oxygen atom or N-CN
  • J is CR 1 R 2 or NR 3 .
  • R 1 is a C1-C3 alkyl group
  • R 2 is a hydrogen atom
  • R 3 is a hydrogen atom or a C1-C6 chain hydrocarbon group
  • X is CR 5 R 6 R 7 or C3-C6
  • R 5 , R 6 and R 7 are each independently a hydrogen atom, a halogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms
  • G is a benzene ring optionally having one or more fluorine atoms
  • Q is an oxygen atom or an N-CN group
  • m is 1
  • J is CR 1 R 2 or NR 3
  • X is CR 5 R 6 R 7 or a C3-C6 cycloalkyl group
  • R 5 , R 6 and R 7 are each independently a hydrogen atom, a halogen atom or one or more
  • An oxadiazole compound which is a C1-C6 chain hydrocarbon group which may have a halogen atom, and J is bonded to the para position with respect to the oxadiazole ring.
  • G is a benzene ring
  • Q is an oxygen atom or N-CN
  • m is 1
  • X is CR 5 R 6 R 7 , R 5 , R 6 , And R 7 are each independently a hydrogen atom, a halogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms
  • J is in the para position relative to the oxadiazole ring A bonded oxadiazole compound.
  • G is a benzene ring
  • Q is an oxygen atom or N-CN
  • m is 1
  • X is CR 5 R 6 R 7 , R 5 , R 6 , And R 7 each independently represents a hydrogen atom, a halogen atom or a C1-C6 chain hydrocarbon group, and J is bonded to the para position with respect to the oxadiazole ring.
  • G is a benzene ring optionally having one or more fluorine atoms
  • Q is an oxygen atom
  • n 2
  • J is CR 1 R 2
  • X is NR 8 R 9
  • R 1 is a C1-C3 alkyl group
  • R 2 is a hydrogen atom or a C1-C3 alkyl group
  • R 8 is one or more selected from the group consisting of a halogen atom and a cyano group
  • a C2-C6 alkyl group optionally having a substituent
  • R 9 is a C2-C6 alkyl group having one or more substituents selected from the group consisting of a halogen atom and a cyano group
  • G is a benzene ring
  • Q is an oxygen atom
  • n is 2
  • J is CR 1 R 2 or NR 3
  • R 1 is a C1-C3 alkyl group.
  • R 2 is a hydrogen atom
  • R 3 is a hydrogen atom or a C1-C3 chain hydrocarbon group
  • X is a CR 5 R 6 R 7 or C3-C6 cycloalkyl group
  • R 5 , R 6 And R 7 each independently represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group
  • J is bonded to the para-position relative to the oxadiazole ring on the benzene ring.
  • G is a benzene ring
  • Q is an oxygen atom
  • n is 2
  • J is CR 1 R 2
  • R 1 is a C1-C3 alkyl group
  • R 2 Is a hydrogen atom
  • X is CR 5 R 6 R 7
  • R 5 , R 6 and R 7 are each independently a hydrogen atom or a C1-C6 alkyl group
  • J is an oxadiazole on the benzene ring An oxadiazole compound bonded to the para position relative to the ring.
  • the compound of the present invention can be produced, for example, by the following production method.
  • the compound of the present invention can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with trifluoroacetic anhydride in the presence of a base.
  • A1 a compound represented by formula (A1)
  • trifluoroacetic anhydride 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), N, N Acid amides such as dimethylformamide, 1,3-dimethyl-2-imidazolidinone, 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 ( Below referred to as sulfoxide.), Nitriles such as acetonitrile and propionitrile (hereinafter, referred to as nitriles.), Water and mixtures thereof.
  • ethers Ethers such as methyl tert-butyl ether and diisopropyl ether (her
  • 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. (Hereinafter referred to as “carbonates”), and bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as bicarbonates).
  • organic bases such as triethylamine, pyridine, 2,2′-bipyridine, diazabicycloundecene
  • carbonates such as sodium carbonate and potassium carbonate
  • bicarbonates such as sodium bicarbonate and potassium bicarbonate
  • 1 to 10 mol of trifluoroacetic anhydride and 1 to 10 mol of base are used per 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 extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • the compound of the present invention can also be isolated by adding water to the reaction mixture and collecting the precipitate by filtration.
  • a compound represented by formula (1B) (hereinafter referred to as compound (1B)) and a compound represented by formula (1C) (hereinafter referred to as compound (1C)) are compounds represented by formula (1A) ( Hereinafter, it can be produced by reacting the compound (1A) with an oxidizing agent. [Wherein the symbols have the same meaning as described above. ] 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.
  • Examples of the oxidizing agent used in the reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, and potassium periodate.
  • a base may be added to the reaction, and examples of the base include carbonates such as sodium carbonate and potassium carbonate.
  • Additives may be added to the reaction, and examples thereof include trifluoroacetic acid and ruthenium (III) chloride hydrate.
  • the reaction is usually carried out in a proportion of 1 to 1.9 mol of the oxidizing agent, 1 to 10 mol of the base and 0.01 to 10 mol of the additive with respect to 1 mol of the compound (1A). Used in a proportion of 10 moles.
  • the reaction is usually carried out in a proportion of 2 to 10 mol of the oxidizing agent, 1 to 10 mol of the base, and 0.01 to 10 mol of the additive with respect to 1 mol of the compound (1A). It is used in the ratio.
  • 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 (1B) or the compound (1C) is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. Can do.
  • Manufacturing method C The compound represented by the formula (1E) can be produced according to the production method B using the compound represented by the formula (1D) and an oxidizing agent.
  • Q 1 represents CN, NO 2 , C (O) R 4 , or C (O) OR 4 , and other symbols represent the same meaning as described above.
  • the compound represented by the formula (1D1) (hereinafter referred to as the compound (1D1)) can be produced by reacting the compound (1A) with cyanamide (NH 2 CN) in the presence of an additive.
  • 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 additive used in the reaction include diacetoxyphenyl iodide and bis (trifluoroacetoxy) phenyl iodide.
  • cyanamide is usually used in a proportion of 1 to 10 mol and an additive is used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (1A).
  • 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 (1D1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer.
  • a compound represented by formula (1F2) (hereinafter referred to as compound (1F2)) is a compound represented by formula (1F1) (hereinafter referred to as compound (1F1)) and a compound represented by formula (M1) ( Hereinafter, it can be produced by reacting the compound (M1)) in the presence of a base.
  • X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, and the other symbols have the same meaning as described above]
  • the reaction is usually performed in a solvent.
  • Examples of the solvent used for the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixtures thereof.
  • Examples of the base used in the reaction include organic bases, carbonates, hydrogen carbonates, and metal hydrides such as sodium hydride, potassium hydride, and lithium hydride.
  • the compound (M1) 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 (1F1).
  • 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 (1F2) 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 A Compound (A1) can be produced by reacting hydroxylamine with a compound represented by formula (A2) (hereinafter referred to as compound (A2)). [Wherein the symbols have the same meaning as described above. ] The reaction is known or can be carried out according to the method described in Patent Document 1, for example.
  • 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%.
  • 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 ( Examples thereof include 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 hexane, kerosene
  • esters nitriles, ethers, acid amides, and halogenated hydrocarbons.
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Is mentioned.
  • formulation adjuvants include, for example, 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, polyvinylpyrrolidone, polyacrylic acids), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4 -Mixtures of -methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
  • polysaccharides eg, starch, arabic gum, cellulose derivatives, alginic acid
  • lignin derivatives bentonite
  • Saccharides synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinylpyrrolidone, poly
  • 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 ( Registration Target), 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.
  • 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. In this case, 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, coral rabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables ( Burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery vegetables (carrots, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.), perilla Vegetables (Perilla, Mint, Basil) ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants, Fruit trees; pears (app
  • 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.
  • plague (Phytophthora parasitica, Phytophthora citrophthora); apple monilia (Monilinia mala) i), rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria alternata apple pathotype), black scab (Venturia inaequalis), anthracnose (Glomerella cingulata), brown spot (Diplocarpon mali) Botryosphaeria berengeriana, plague (Phytophtora cactorum); pear black spot (Venturia nashicola, V.
  • pirina black spot (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); Disease (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp.
  • Sp subterranea
  • half body wilt disease Verticillium albo-atrum, V. dahliae, V. nigrescens
  • strawberry powdery mildew (Sphaerotheca humuli); chamodium rot (Exobasidium reticulatum), white star disease (Elsinoe leucospila), circle Spot disease (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); Tobacco Red Star Disease (Alternaria longipes), Anthracnose (Colletotrichum tabacum), Downy Mildew (Peronospora tabacina), Plague (Phytophthora nicotianae); Brown spot disease (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides); Brown spot (S
  • Botrytis cinerea of various crops Sclerotinia sclerotiorum; Alternaria brassicicola; Sclerotinia homeocarpa; Brown patch disease of lava -Rhizoctonia solani; and banana sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
  • 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 Polymixa genus or Olpidium genus.
  • Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citiri); 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; Pluteliidae such as Plutella xylostella; Plumeliidae; 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 root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cucumber beetle Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Bark beetle beetle (Oulema melanopus), Root beetle (Aulacophora femoralis), Phyllotreta striolifer beetle (West) black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle (Oule
  • Carabidae such as Carabidae
  • Anomala cuprea such as Carabidae
  • Anomala rufocuprea such as Anomala albopilosa
  • Popillia japonica Heptophylla picea
  • Majoriotrotro European Chagus
  • Scarabaeidae Diloboderus spp.
  • Scaridae family Diloboderus spp.
  • Cotton beetle weevil (Araecerus coffeae), green weevil (Cylas formicarius), weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), weevil (Sitophilus zeamais), zomus mus (E) White weevil (Rhabdoscelus lineatocollis), Cotton weevil (Anthonomus grandis), White weevil (Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcophor weevil The weevil (Scepticus griseus), the flying white weevil (Scepticus uniformis), the Brazilian weevil (Zabrotes subfasciatus), the pine beetle (Tomicus piniperda), the Coffee Berry Borer (Hypothenemus hampei),
  • Curculionidae such as cotton root borer (Eutinobothrus brasiliensis); Tribolium castaneum; Coccinellidae; Nagashimidae (Bostrychidae) such as Lyctus brunneus; Ptinidae; Anoplophora malasiaca, Migdolus fryanus notus okinawensis), Agrobotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., L spp.), Aeolus spp., etc.
  • 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.
  • Formula (a) In which the combination of R 5 , R 6 and R 7 is the combination described in [Table 1],
  • Compound 20 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.10-8.07 (2H, m), 7.38-7.34 (2H, m), 6.93 (1H, s), 3.44-3.37 (1H, m), 1.44 (6H, d).
  • Compound 21 of the present invention 1 H-NMR (DMSO-D 6 ) ⁇ : 10.46 (1H, s), 7.80-7.77 (2H, m), 7.38-7.34 (2H, m), 2.83-2.77 (1H, m) , 1.04-0.96 (4H, m).
  • Compound 22 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.18 (2H, d), 8.06 (1H, s), 7.78 (2H, d).
  • 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 (b) In which the combination of R 5 , R 6 and R 7 is the combination described in [Table 3].
  • Production Example 3-2 The compound 7 of the present invention was obtained according to the method described in Production Example 3-1.
  • Formula (c) In which the combination of R 5 , R 6 and R 7 is the combination described in [Table 4].
  • Production Example 4-2 The compound 18 of the present invention was obtained according to the method described in Production Example 4-1.
  • Compound 18 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.22-8.20 (2H, m), 7.51-7.49 (2H, m), 4.35 (1H, q), 2.57 (3H, s), 1.92 (3H , d).
  • Production Example 5-2 The compound 19 of the present invention was obtained according to the method described in Production Example 5-1.
  • Compound 19 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.25-8.22 (2H, m), 7.67-7.64 (2H, m), 4.65 (1H, q), 2.97 (3H, s), 2.01 (3H , d).
  • Production Example 6-2 The compounds 23 to 29 of the present invention were produced according to the method described in Production Example 6-1. The structure and physical properties are shown below. Formula (d) In which R 3 is any one of those described in [Table 5].
  • Production Example 7 The compound 15 of the present invention was produced according to the method described in Production Example 1-1. The structure and physical properties are shown below.
  • Compound 15 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.09-8.06 (2H, m), 7.51-7.49 (2H, m), 3.94-3.89 (1H, m), 1.93 (3H, s), 1.62 (3H, d).
  • Production Example 8 The compound 16 of the present invention was produced according to the method described in Production Example 3-1. The structure and physical properties are shown below.
  • Compound 16 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 8.19-8.16 (2H, m), 7.65-7.62 (2H, m), 4.28 (1H, q), 2.72 (3H, s), 1.85 (3H , d).
  • Production Example 9-1 A mixture of 1.9 g of 4- (1,1-dioxo-2-isothiazolidinyl) benzonitrile, 50 mL of ethanol, and 2.1 mL of 50% -hydroxylamine aqueous solution was stirred under reflux for 4 hours. After cooling the mixture to 0 ° C., the precipitate was collected by filtration. The obtained solid was dried under reduced pressure. To a mixture of the solid and 30 mL of N, N-dimethylformamide, 1.9 mL of pyridine and 1.3 mL of trifluoroacetic anhydride were sequentially added at room temperature, followed by stirring at 90 ° C. for 10 hours. The mixture was cooled to room temperature and 200 mL of water was added.
  • Production Example 9-2 The compound 32 of the present invention was produced according to the method described in Production Example 9-1. The structure and physical properties are shown below.
  • Compound 32 of the present invention 1 H-NMR (DMSO-D 6 ) ⁇ : 8.08-8.05 (2H, m), 7.56-7.54 (2H, m), 3.79-3.76 (2H, m), 3.37-3.33 (2H, m), 2.20-2.17 (2H, m), 1.86-1.83 (2H, m).
  • 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
  • CN represents a cyano group
  • Ph represents a phenyl group
  • Bn represents a benzyl group Represents.
  • R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or any substituent selected from group E, and R 15 represents one or more substituents selected from group A.
  • a C1-C6 alkyl group optionally having one or more, a C3-C6 cycloalkyl group optionally having one or more substituents selected from the group consisting of a halogen atom and a cyano group, or a halogen atom and a cyano group Represents a phenyl group optionally having one or more substituents selected from the group consisting of ]
  • the combination of R 11 , R 12 , R 13 , R 14 and R 15 is a combination described in any one of the substituent numbers RA1 to RA105 shown below (hereinafter referred to as a substituent)
  • Compounds of the group numbers RA1 to RA105 are represented as the compounds of the present invention RA1 to RA105, and the compounds of the present invention RA
  • the substituent numbers RA1 to RA105 represent combinations of R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (II). ; R 11 , R 12 , R 13 , R 14 , R 15 ].
  • the substituent number RA4 represents a combination in which R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • the present compound RA4 means a compound having a substituent number of RA4.
  • R 11 , R 12 , R 13 and R 14 are hydrogen atoms
  • R 15 is Represents a compound that is an isopropyl group.
  • R 11 , R 12 , R 13 , R 14 and R 15 represent the same meaning as described above.
  • the combination of R 11 , R 12 , R 13 , R 14, and R 15 is a combination described in any one of the substituent numbers RB1 to RB105 shown below (hereinafter referred to as substitution)
  • the compounds of the group numbers RB1 to RB105 are represented as the compounds RB1 to RB105 of the present invention, and the compounds RB1 to RB105 of the present invention are collectively represented as the compound RB of the present invention).
  • the substituent numbers RB1 to RB105 represent combinations of R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (III).
  • the substituent number RB4 represents a combination in which R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • this compound RB4 means a compound whose substituent number is RB4, and in the compound represented by the formula (III), R 11 , R 12 , R 13 and R 14 are hydrogen atoms, and R 15 is Represents a compound that is an isopropyl group.
  • the substituent numbers RC1 to RC105 represent combinations of R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (IV). ; R 11 , R 12 , R 13 , R 14 , R 15 ].
  • the substituent number RC4 represents a combination in which R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • the present compound RC4 means a compound whose substituent number is RC4.
  • R 11 , R 12 , R 13 and R 14 are hydrogen atoms
  • R 15 is Represents a compound that is an isopropyl group.
  • the substituent numbers RD1 to RD105 represent combinations of R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (V). ; R 11 , R 12 , R 13 , R 14 , R 15 ].
  • the substituent number RD4 represents a combination in which R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • the present compound RD4 means a compound whose substituent number is RD4, and in the compound represented by the formula (V), R 11 , R 12 , R 13 and R 14 are hydrogen atoms, and R 15 is Represents a compound that is an isopropyl group.
  • R 11 , R 12 , R 13 , R 14 and R 15 represent the same meaning as described above.
  • the combination of R 11 , R 12 , R 13 , R 14 and R 15 is a combination described in any one of the substituent numbers RE1 to RE105 shown below (hereinafter referred to as a substituent)
  • the compounds of the group numbers RE1 to RE105 are represented as the compounds of the present invention RE1 to RE105, and the compounds of the present invention RE1 to RE105 are collectively represented as the compound of the present invention RE).
  • the substituent numbers RE1 to RE105 represent combinations of R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (VI).
  • R 11 , R 12 , R 13 , R 14 , R 15 the substituent number RE4 represents a combination in which R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • the present compound RE4 means a compound whose substituent number is RE4.
  • R 11 , R 12 , R 13 and R 14 are hydrogen atoms
  • R 15 is Represents a compound that is an isopropyl group.
  • the substituent numbers RF1 to RF165 represent combinations of R 3 , R 11 , R 12 , R 13 , R 14 and R 15 in the compound represented by the formula (VII). Substituent number: R 3 , R 11 , R 12 , R 13 , R 14 , R 15 ]
  • the substituent number RF4 represents a combination in which R 3 , R 11 , R 12 , R 13 and R 14 are hydrogen atoms and R 15 is an isopropyl group.
  • the present compound RF4 means a compound whose substituent number is RF4, and in the compound represented by the formula (VII), R 3 , R 11 , R 12 , R 13 and R 14 are hydrogen atoms, R 15 represents a compound having an isopropyl group.
  • R 1 , R 2 and R 15 represent the same meaning as described above.
  • the combination of R 1 , R 2 and R 15 is a combination described in any one of the substituent numbers RG1 to RG60 shown below (hereinafter referred to as substituent numbers RG1 to RG60).
  • the compounds are represented as the present compounds RG1 to RG60, and the present compounds RG1 to RG60 are collectively referred to as the present compound RG), which can be obtained according to the method described in the above production method.
  • the substituent numbers RG1 to RG60 represent a combination of R 1 , R 2 and R 15 in the compound represented by the formula (VIII).
  • R 1 , R 2 , R 15 [Substituent numbers; R 1 , R 2 , R 15 ].
  • the substituent number RG4 represents a combination in which R 1 is a methyl group, R 2 is a hydrogen atom, and R 15 is an isopropyl group.
  • the present compound RG4 means a compound having a substituent number of RG4.
  • R 1 is a methyl group
  • R 2 is a hydrogen atom
  • R 15 is isopropyl.
  • the compound which is group is represented.
  • R 1 , R 2 and R 15 represent the same meaning as described above.
  • the combination of R 1 , R 2, and R 15 is a combination described in any one of the substituent numbers RH1 to RH60 shown below (hereinafter, the substituents of RH1 to RH60
  • the compounds are represented by the compounds of the present invention RH1 to RH60, and the compounds of the present invention RH1 to RH60 are collectively represented as the compound of the present invention RH).
  • the substituent numbers RH1 to RH60 represent combinations of R 1 , R 2 and R 15 in the compound represented by the formula (IX).
  • the substituent number RH4 represents a combination in which R 1 is a methyl group, R 2 is a hydrogen atom, and R 15 is an isopropyl group.
  • RH4 means a compound having a substituent number of RH4.
  • R 1 is a methyl group
  • R 2 is a hydrogen atom
  • R 15 is isopropyl.
  • the compound which is group is represented.
  • R 8 and R 9 represent the same meaning as described above.
  • the combination of R 8 and R 9 is a combination described in any of the substituent numbers RI1 to RI13 shown below (hereinafter, the compounds having the substituent numbers RI1 to RI13 are Inventive compounds RI1 to RI13 and present compounds RI1 to RI13 are collectively referred to as present compound RI) can be obtained according to the method described in the above production method.
  • the substituent numbers RI1 to RI13 represent combinations of R 8 and R 9 in the compound represented by the formula (X), and are hereinafter referred to as [substituent numbers; R 8 , R 9 ].
  • the substituent number RI4 represents a combination in which R 8 is a hydrogen atom and R 9 is an isopropyl group.
  • the present compound RI4 means a compound having a substituent number of RI4, and in the compound represented by the formula (X), R 8 is a hydrogen atom and R 9 is an isopropyl group.
  • substitution a combination described in any one of the substituent numbers RJ1 to RJ168 shown below (hereinafter referred to as substitution)
  • the compounds of the group numbers RJ1 to RJ168 are represented by the compounds RJ1 to RJ168 of the present invention, and the compounds RJ1 to RJ168 of the present invention are collectively represented as the compound RJ of the present invention).
  • the substituent numbers RJ1 to RJ168 represent combinations of A 1 , A 2 , A 3 , A 4 , Q 1 and R 15 in the compound represented by the formula (XI). Substituent number: A 1 , A 2 , A 3 , A 4 , Q 1 , R 15 ]
  • the substituent number RJ4 represents a compound in which A 1 is a nitrogen atom, A 2 , A 3 and A 4 are CH, Q 1 is an oxygen atom, and R 15 is an isopropyl group.
  • the present compound RA, the present compound RB, the present compound RC, the present compound RD, the present compound RE, the present compound RF, the present compound RG, the present compound RH, the present compound RI and the present compound RJ This is referred to as Compound A of the present invention.
  • the compound of the present invention is used in combination or in combination with a fungicide, insecticide, acaricide, nematocide, plant growth regulator or synergist (hereinafter, the active ingredient in each agent is referred to as the active ingredient).
  • the active ingredient in each agent is referred to as the active ingredient.
  • the abbreviation SX means any one compound selected from the compound A of the present invention.
  • the numbers in parentheses represent CAS registration numbers.
  • the mixing ratio of the compound of the present invention and 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 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 After mixing 20 parts of any one of the compounds A of the present invention and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and finely pulverizing by a wet pulverization method, Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.
  • Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one compound of the present compound A, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the compounds A of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 After thoroughly mixing 2 parts of any one of the compounds A of the present invention, 1 part of synthetic hydrous oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, add water and knead well The preparation is obtained by 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 Example 1 Control test against tomato leaf mold (Cladosporium fulvum)
  • the compound 3, 9, 11, 18, 21, 22, 24 or 31 of the present invention was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and titer plate (96 well) 1 ⁇ L of the tomato leaf mold (QoI-resistant strain whose base sequence was mutated so that the 129th amino acid residue of cytochrome b was replaced by phenylalanine to leucine among the genes encoding cytochrome b)
  • PDB medium potato broth liquid medium
  • the growth degree in the group treated with the compound 3, 9, 11, 18, 21, 22, 24, or 31 of the present invention was 50% or less of the growth degree in the untreated group.
  • Test Example 2 Control Test Against Wheat Leaf Blight Fungus (Septoria tritici)
  • the present compound 2, 4-7, 11-14, 16, 18, 22, or 27 was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and a titer plate (96 1 ⁇ L was dispensed into a well), and then 150 ⁇ L of a potato broth liquid medium (PDB medium) inoculated with spores of wheat leaf blight was previously dispensed.
  • PDB medium potato broth liquid medium
  • This plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight fungi.
  • 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 group treated with the present compound 2, 4-7, 11-14, 16, 18, 22, or 27 was 50% or less of the growth degree in the untreated group.
  • Test Example 3 Control Test for Soybean Anthracnose (Colletotrichum truncatum) Diluted with dimethyl sulfoxide so as to contain 1500 ppm of the present compound 11 or 12 and dispensed 1 ⁇ L into a titer plate (96-well), and then spores of soybean anthracnose 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 4 days to propagate soybean anthracnose fungi, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the degree of growth of soybean anthracnose fungus.
  • the degree of growth in the group treated with the present compound 11 or 12 was 50% or less of the degree of growth in the untreated group.
  • Test Example 4 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, sowed with wheat (variety: Shirogane), and cultivated in a greenhouse for 9 days.
  • the compounds of the present invention 3 to 8, 10, 11, 13, 14, 16, 17, 19, 21 to 31 or 32 formulated according to the method described in Formulation Example 6 are mixed with water so that the concentration becomes 500 ppm. After mixing, 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 compounds of the present invention 3 to 8, 10, 11, 13, 14, 16, 17, 19, 21 to 31 or 32 is the same as the lesion area in the untreated wheat. It was 30% or less.
  • Test Example 5 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 compound 3-7, 9, 10, 13, 14, 16-19 or 21 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 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 cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus.
  • the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination.
  • the lesion area in the wheat treated with the present compounds 3 to 7, 9, 10, 13, 14, 16 to 19 or 21 was 30% or less of the lesion area in the untreated wheat. .
  • Test Example 6 Control Trial for Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, seeded with wheat (variety: Apogee), and cultivated in a greenhouse for 10 days. Compound 2-12, 14, 16, 17, 19, 21, 24, 27-30 or 32 of the present invention 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 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.
  • the lesion area in the wheat treated with the compounds 2-12, 14, 16, 17, 19, 21, 24, 27-30 or 32 of the present invention was 30% of the lesion area in the untreated wheat. It was the following.
  • Test Example 7 Control Trial for Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, seeded with wheat (variety: Apogee), and cultivated in a greenhouse for 10 days. Compound of the present invention 2, 3, 4, 6, 7, 9, 10, 12, 13, 14, 17, 19, 21, 23 to 29 or 30 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 leaf surface 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. After inoculation, the wheat was placed under high humidity at 18 ° C.
  • Test Example 8 Control Test for Soybean Rust (Phakopsora pachyrhizi) Filled with plastic soil in a plastic pot, seeded with soybean (variety; Kurosengoku), cultivated 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 soybean treated with the present compounds 1 to 10, 13 to 19, 21 to 31 or 32 was 30% or less of the lesion area in the untreated soybean.
  • Test Example 9 Control Test for Soybean Rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and soybean (cultivar; Kurosengoku) was sown therein and cultivated in a greenhouse for 13 days.
  • the compounds 3-19, 21, 23-31 or 32 of the present invention formulated according to the method described in Formulation Example 6 are mixed with water to a concentration of 200 ppm, and the mixture is added to the soybean leaf surface.
  • the foliage was sprayed so as to adhere well. After spraying, the soybeans were air-dried, and after 4 days, sprayed with a water suspension of soybean rust spores. After inoculation, soybeans were placed in a humid room at 23 ° C.
  • the lesion area in soybean treated with the present compounds 3-19, 21, 23-31 or 32 was 30% or less of the lesion area in untreated soybean.
  • Test Example 10 Control test against barley net spot disease (Pyrenophora teres) A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days.
  • the compound 5, 9 or 21 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration is 500 ppm, and the mixture is sufficiently adhered to the leaf surface of the barley.
  • the foliage was sprayed on the ground. 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 compound 5, 9 or 21 of the present invention was 30% or less of the lesion area in the untreated barley.
  • Test Example 11 Control test against barley cloud disease (Rhynchosporium secalis) A plastic pot was stuffed with soil, seeded with barley (variety: Nishinohoshi), and cultivated in a greenhouse for 7 days.
  • the compound 1 of the present invention formulated according to the method described in Formulation Example 6 was mixed with water to a concentration of 200 ppm, and the mixture was sprayed on the foliage so that the mixture sufficiently adhered to the leaf surface of the barley. 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 Compound 1 of the present invention was 30% or less of the lesion area in the untreated barley.
  • Test Example 12 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days. Thereafter, the compound 1, 2, 5, 6, 8, 23 or 26 of the present invention formulated according to the method described in Formulation Example 6 was mixed with water to a concentration of 500 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 1, 2, 5, 6, 8, 23 or 26 was 30% or less of the lesion area in the untreated rice.
  • Test Example 13 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown therein, and cultivated in a greenhouse for 20 days. Thereafter, the compound 1, 4, 6, 12, 14, 26 or 29 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm, and the mixture is mixed with the above-mentioned mixture. The foliage was sprayed so as to adhere well to the leaf surface of 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 the rice treated with the compound 1, 4, 6, 14, 26 or 29 of the present invention was 30% or less of the lesion area in the untreated rice.
  • Test Example 14 Control test against cucumber anthracnose (Colletotrichum lagenarium) A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown therein and cultivated in a greenhouse for 19 days.
  • the compound 9 of the present invention formulated in accordance with the method described in Formulation Example 6 was mixed with water to a concentration of 200 ppm, and the mixture was sprayed on the foliage so that the mixture was sufficiently attached 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.
  • the lesion area in the cucumber treated with the compound 9 of the present invention was 30% or less of the lesion area in the untreated cucumber.
  • reference compounds show that the compounds of the present invention are useful for controlling harmful arthropods.
  • Reference test example 1 About 30 cotton aphids (Aphis gossypii, all stages) were inoculated into a cucumber seedling (second true leaf development stage) planted in a container and allowed to stand for 1 day.
  • the compound 7, 8 or 9 of the present invention formulated according to the method described in Formulation Example 6 is adjusted with water so that the concentration is 500 ppm, and the adjusted solution is added to the seedlings at a rate of 10 mL / seedling. Scattered. Further, after 5 days, the number of live insects was investigated, and the control value was determined by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai Number of live insects at the time of survey in the treated group It means a group that performs the same operation as the treatment group except that the compound of the present invention is not used.
  • the treatment group of the present compound 7, 8 or 9 showed a control value of 90% or more.
  • 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 6 of the present invention formulated according to the method described in Formulation Example 6 is added to the resulting slurry solution, so that 500 ⁇ g of the compound 6, 18 or 19 of the present invention per 1 g of corn seed adheres. The seeds were coated. 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).
  • 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.

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

Abstract

L'invention concerne des composés oxadiazole représentés par la formule (1) [dans la formule, G représente un noyau thiophène, un noyau furane, 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 pyridazine, un noyau pyrimidine, ou un noyau benzène substitué ou non substitué, J représente ＣＲ1Ｒ2、ＮＲ3, ou un atome d'oxygène, Q représente un atome d'oxygène, Ｎ－ＣＮ、Ｎ－ＮＯ2、Ｎ－Ｃ（Ｏ）Ｒ4, ou Ｎ－Ｃ（Ｏ）ＯＲ4 (cependant, Q peut être identique ou différent lorsque n est 2), X représente ＣＲ5Ｒ6Ｒ7、ＮＲ8Ｒ9、ＯＲ10, ou un groupe hétéroaryle de 5 ou 6 chaînons, ou similaire, m représente 0 ou 1, et n représente 0, 1 ou 2.] et un agent de lutte contre les maladies des plantes mettant en œuvre ces derniers.
PCT/JP2016/088634 2015-12-25 2016-12-26 Composés oxadiazole et leur utilisation WO2017111152A1 (fr)

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WO2018080859A1 (fr) * 2016-10-24 2018-05-03 E. I. Du Pont De Nemours And Company Oxadiazoles fongicides
US20180362515A1 (en) * 2015-12-02 2018-12-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2019097054A1 (fr) * 2017-11-20 2019-05-23 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
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
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
JP2021507911A (ja) * 2017-12-20 2021-02-25 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ フルオロアルケニル化合物、その製造法およびその使用
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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
WO2022129190A1 (fr) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides
RU2805208C2 (ru) * 2018-01-30 2023-10-12 Пи Индастриз Лтд. Новые оксадиазолы
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

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US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
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US20180362515A1 (en) * 2015-12-02 2018-12-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11259524B2 (en) 2016-01-08 2022-03-01 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
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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
WO2019097054A1 (fr) * 2017-11-20 2019-05-23 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
JP2021507911A (ja) * 2017-12-20 2021-02-25 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ フルオロアルケニル化合物、その製造法およびその使用
RU2805208C2 (ru) * 2018-01-30 2023-10-12 Пи Индастриз Лтд. Новые оксадиазолы
WO2019150219A3 (fr) * 2018-01-30 2019-09-26 Pi Industries Ltd. Nouveaux oxadiazoles
AU2019213693B2 (en) * 2018-01-30 2022-09-22 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
JP7538041B2 (ja) 2018-01-30 2024-08-21 ピーアイ インダストリーズ リミテッド 新規オキサジアゾール類
CN112004813B (zh) * 2018-01-30 2024-03-29 Pi工业有限公司 用于控制植物病原性真菌的噁二唑化合物
JP2021512088A (ja) * 2018-01-30 2021-05-13 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ 新規オキサジアゾール類
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
CN112004813A (zh) * 2018-01-30 2020-11-27 Pi工业有限公司 用于控制植物病原体真菌的噁二唑化合物
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
JP2022501410A (ja) * 2018-10-01 2022-01-06 ピーアイ インダストリーズ リミテッドPi Industries Ltd 新規なオキサジアゾール
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
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
WO2022129190A1 (fr) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazoles substitués par (hétéro)aryle utilisés comme fongicides

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