WO2014115834A1 - Composé d'azolyloxime ou sel de celui-ci, agent pesticide, insecticide ou acaricide, désinfectant, et agent antiparasitaire externe - Google Patents

Composé d'azolyloxime ou sel de celui-ci, agent pesticide, insecticide ou acaricide, désinfectant, et agent antiparasitaire externe Download PDF

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WO2014115834A1
WO2014115834A1 PCT/JP2014/051486 JP2014051486W WO2014115834A1 WO 2014115834 A1 WO2014115834 A1 WO 2014115834A1 JP 2014051486 W JP2014051486 W JP 2014051486W WO 2014115834 A1 WO2014115834 A1 WO 2014115834A1
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衆一 伊藤
純司 一法師
睦大 天野
岩田　淳
伸哉 幸堀
里枝 坂本
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日本曹達株式会社
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Definitions

  • the present invention relates to azolyl oxime compounds, pest control agents, insecticides or acaricides, fungicides, and ectoparasite control agents. More specifically, the present invention relates to an azolyloxime compound or a salt thereof, which has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially, and harmful substances containing this as an active ingredient. The present invention relates to biocontrol agents, insecticides or acaricides, fungicides, and ectoparasite control agents. This application claims priority based on Japanese Patent Application No. 2013-012989 filed in Japan on January 28, 2013, the contents of which are incorporated herein by reference.
  • Patent Document 1 discloses an azolyl oxime compound having naphthyl or pyridyl and triazolyl or imidazolyl in the molecular structure. Patent Document 1 states that some of the compounds had an insecticidal effect against leafhopper, leafhopper, and diamondback moth. However, other compounds are merely described as potential insecticides.
  • Patent Document 2 discloses a pyridine derivative. An azolyl oxime compound is disclosed as one of the pyridine derivatives. Patent Document 2 states that some of the compounds had an insecticidal effect against peach aphid, brown planthopper, silver leaf whitefly, and the like. However, other compounds are merely described as potential insecticides.
  • “Azolyl” is a 5-membered saturated or unsaturated heterocyclyl group having two or more hetero atoms selected from the group consisting of a nitrogen atom, a sulfur atom and an oxygen atom as ring member atoms, and at least one of the hetero atoms.
  • One is a nitrogen atom.
  • Specific examples include triazolyl and imidazolyl.
  • An object of the present invention is to provide an azolyl oxime compound or a salt thereof, which is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized advantageously industrially, and It is to provide a pest control agent containing an active ingredient as an active ingredient, and an insecticide or acaricide. Furthermore, it is providing the bactericidal agent containing this as an active ingredient, and an ectoparasite control agent.
  • an azolyloxime compound having a specific structure such as a diazine ring or a triazine ring or a salt thereof has excellent insecticidal activity and / or acaricidal activity, It was also found that it has good characteristics and high safety and can be used as an active ingredient of a pest control agent. Furthermore, it discovered that it could utilize as an active ingredient of a disinfectant and an ectoparasite control agent. The present invention has been completed based on this finding.
  • the present invention includes the following.
  • Het represents a 6-membered heteroaryl ring containing 2 to 3 nitrogen atoms as constituent atoms of the ring.
  • X 1 is a substituent on Het, which is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 -6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy Group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C3-8 cycloalkyloxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted Or a substituted C1-6 alkoxycarbonyl group, an unsubstituted
  • X 1 may be the same as or different from each other.
  • A represents a carbon atom or a nitrogen atom.
  • X 2 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, a hydroxy group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group A C1-6 alkoxycarbonyl group, an unsubstituted or substituted amino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl group, Unsubstituted or substituted C6-10
  • n represents the number of X 2 and is an integer from 0 to 3. When n is 2 or more, X 2 may be the same as or different from each other.
  • R 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclyl group is shown.
  • a bond represented by crossed solid lines represents a double bond having stereoisomerism.
  • X 11 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl Group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted amino group, unsubstituted or substituted A C1-6 alkylthio group having a group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group .
  • m1 represents the number of X 11 and is an integer from 0 to 2. When m1 is 2 or more, X 11 may be the same as or different from each other.
  • the bonds represented by X 1 , A, X 2 , n, R 1 and the crossed solid line are as described above.
  • a pest control agent comprising as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
  • An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
  • a bactericide containing as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
  • An ectoparasite control agent comprising as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] above and a salt thereof.
  • the azolyloxime compound or a salt thereof of the present invention can control pests that are problematic in terms of crops and hygiene.
  • agricultural pests and mites can be effectively controlled.
  • plant diseases can be effectively controlled.
  • ectoparasites that harm human livestock can be effectively controlled.
  • the azolyloxime compound of the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as compound (I)).
  • the term “unsubstituted” means only a group serving as a mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
  • the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus.
  • the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
  • C1-6 indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Examples of groups that can be “substituents” are shown below. C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • An alkyl group Vinyl group, 1-propenyl group, 2-propenyl group (also known as allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group
  • a C2-6 alkenyl group such as a group
  • C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group
  • a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group
  • a C4-8 cycloalkenyl group such as a
  • a C6-10 aryl group such as a phenyl group or a naphthyl group
  • a C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group
  • 3-6 membered heterocyclyl group
  • a C1-7 acyl group such as a formyl group, an acetyl group, a propionyl group, a benzoyl group, a cyclohexylcarbonyl group
  • a hydroxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryloxy groups such as phenoxy group and 1-naphthoxy group; A C6-10 aryl C1-6 alkoxy group such as a benzyloxy group or a phenethyloxy group; A 3-6 membered heterocyclyloxy group; A 3-6 membered heterocyclyl C1-6 alkoxy group;
  • C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group;
  • a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group; Carboxyl group;
  • Halogeno groups such as fluoro, chloro, bromo and iodo groups; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; A C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; A C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C6-10 haloaryl group such as 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group; A C1-6 haloalkoxy group such as a trifluorome
  • a C1-6 alkylamino group such as a methylamino group, a dimethylamino group, a diethylamino group
  • C6-10 arylamino groups such as anilino group and naphthylamino group
  • a C6-10 aryl C1-6 alkylamino group such as a benzylamino group or a phenethylamino group
  • C1-7 acylamino groups such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group
  • a C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group
  • An aminocarbonyl group having no substituent or a substituent such as an amino
  • a mercapto group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
  • a C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
  • a C6-10 aryl C1-6 alkylthio group such as a benzylthio group or a phenethylthio group;
  • a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
  • a C6-10 arylsulfinyl group such as a phenylsulfinyl group;
  • a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group; A triphenylsilyl group; Cyano group; nitro group;
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • the “3- to 6-membered heterocyclyl group” includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms.
  • the heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
  • Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.
  • Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc. .
  • Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridanidyl group, and a triazinyl group.
  • Het represents a 6-membered heteroaryl ring containing 2 to 3 nitrogen atoms as constituent atoms of the ring. Het is preferably a pyrimidine ring.
  • X 1 is a substituent on Het, which is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 -6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy Group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C3-8 cycloalkyloxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted Or a substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, unsubstituted Or a substituted amino group, a
  • the “C1-6 alkyl group” for X 1 may be linear or branched.
  • Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group.
  • examples of the substituent include a halogeno group, a C3-8 cycloalkyl group, a hydroxy group, a C1-6 alkoxy group, a C6-10 aryl group, a C1-7 acyl group, a C1 Up to 6 alkoxycarbonyl groups.
  • C1-6 alkyl group having a substituent include Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2, 2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl Group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, 3,3,4,4,5,5,5 -C1 ⁇ such as heptafluoropentyl group, 2,
  • Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 2-hydroxyethyl group; Methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t
  • a C1-6 alkoxy C1-6 alkyl group such as a butoxyethyl group
  • a C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group
  • C1-7 acyl C1-6 alkyl group such as formylmethyl group, acetylmethyl group, propionylmethyl group
  • a C1-6 alkoxycarbonyl C1-6 alkyl group such as a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxy
  • Examples of the “C2-6 alkenyl group” for X 1 include a vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2 -Propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • Examples of the “substituted C2-6 alkenyl group” include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group.
  • Examples of the “C2-6 alkynyl group” in X 1 include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl Group, 1,1-dimethyl-2-butynyl group and the like.
  • a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group, etc. Etc.
  • Examples of the “C3-8 cycloalkyl group” for X 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.
  • the “C1-6 alkoxy group” in X 1 is a methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group , S-butoxy group, t-butoxy group, i-hexyloxy group, 3,3-dimethylbutoxy group, isopentyloxy group, neopentyloxy group, 2,3,3-trimethylbutoxy group, (4,4- And dimethylpentan-2-yl) oxy group.
  • examples of the substituent include a halogeno group, a C3-8 cycloalkyl group, a hydroxy group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C6-10 aryl group, 3-6 heterocyclyl group, C1-6 alkoxycarbonyl group, C1-6 alkyl substituted amino group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, cyano group, C1-6 alkyl substituted silyl Groups and the like.
  • substituted C1-6 alkoxy group examples include chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy.
  • C3-8 cycloalkyl C1-6 alkoxy groups such as cyclopropylmethoxy group, 2-cyclopropylethoxy group, cyclopentylmethoxy group, cyclohexylmethoxy group, 2-cyclohexylethoxy group; (2,2-difluorocyclopropyl) methoxy group, etc.
  • Hydroxy C1-6 alkoxy groups such as 3-hydroxy-3-methylbutoxy group
  • C1-6 alkoxy C1 such as 2-ethoxyethoxy group, 3-methoxy-3-methylbutoxy group, 2- (t-butoxy) ethoxy group -6 alkoxy group
  • C1-6 haloalkoxy C1-6 alkoxy group such as trifluoromethoxymethoxy group and trifluoromethoxyethoxy group
  • a C6-10 aryl C1-6 alkoxy group such as benzyloxy group, phenoxy group, 3-phenylpropoxy group; (4-methylbenzyl) oxy group, (4-methoxybenzyl) oxy group, (4-trifluorobenzyl) oxy group, (4-fluorobenzyl) oxy group, etc.
  • C1-6 alkoxycarbonyl such as 2- (ethoxycarbonyl) ethoxy group C1-6 alkoxy group; C1-6 such as (1- (dimethylamino) propan-2-yl) oxy group, 2- (dimethylamino) ethoxy group Alkyl substituted amino C1-6 alkoxy group; C1-6 alkylthio C1-6 alkoxy group such as 3- (methylthio) propoxy group; C1-6 alkylsulfinyl C1-6 alkoxy group such as 3- (methylsulfinyl) propoxy group; 3 A C1-6 alkylsulfonyl C1-6 alkoxy group such as a-(methylsulfonyl) propoxy group; a cyano C1-6 alkoxy group such as a 2-cyano-2-methylpropoxy group; a triC1-6 such as a 3- (trimethylsilyl) propoxy group 6 alkyl substituted silyl C1-6 alkoxy groups; It is.
  • Examples of the “C2-6 alkenyloxy group” in X 1 include a vinyloxy group, 1-propenyloxy group, 2-propenyloxy group (allyloxy group), (3-methylbut-2-en-1-yl) oxy group and the like. Can be mentioned.
  • Examples of the “substituted C2-6 alkenyloxy group” include (2,3,3-trifluoroallyl) oxy group, (3,4,4-trifluorobut-3-en-1-yl) oxy group C2-6 haloalkenyloxy groups such as; C6-C10 aryl C2-6 alkenyloxy groups such as (3-phenylallyl) oxy group; and the like.
  • Examples of the “C2-6 alkynyloxy group” for X 1 include ethynyloxy group, prop-2-yn-1-yloxy group, but-2-yn-1-yloxy group and the like.
  • Examples of the “substituted C2-6 alkynyloxy group” include C2 such as 4,4-dichloro-1-butynyloxy group, 4-fluoro-1-pentynyloxy group, 5-bromo-2-pentynyloxy group, etc.
  • C6-C10 aryl C2-6 alkynyloxy groups such as (3-phenylprop-2-yn-1-yl) oxy group;
  • Examples of the “C3-8 cycloalkyloxy group” for X 1 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.
  • Examples of the “substituted C3-8 cycloalkyloxy group” include C3-8 halocycloalkyloxy groups such as (4,4-difluorocyclohexyl) oxy group.
  • Examples of the “C1-7 acyl group” in X 1 include formyl group, acetyl group, propionyl group, benzoyl group and the like.
  • Examples of the “substituted C1-7 acyl group” include C1-7 haloacyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group.
  • Examples of the “C1-6 alkoxycarbonyl group” for X 1 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
  • C1-6 alkylcarbamoyl group for X 1 include a methylcarbamoyl group, an ethylcarbamoyl group, and the like.
  • substituted C1-6 alkylcarbamoyl group include C1-6 haloalkylcarbamoyl groups such as a (2,2,2-trifluoroethyl) carbamoyl group.
  • a C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, a diethylamino group, an isopentylamino group, an isopentyl (methyl) amino group; , 3,3,4,4,4-heptafluorobutyl) amino group and the like, and the like.
  • Examples of the “C1-6 alkylthio group” in X 1 include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, isopentylthio group and the like. Can be mentioned.
  • Examples of the “C1-6 alkylsulfinyl group” in X 1 include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and an isopentylsulfinyl group.
  • Examples of the “C1-6 alkylsulfonyl group” for X 1 include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, an isopentylsulfonyl group, and the like.
  • the “C6-10 aryl group” for X 1 may be monocyclic or polycyclic. In the polycyclic aryl group, if at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “C6-10 aryl group” include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like.
  • the “3- to 6-membered heterocyclyl group” in X 1 includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring constituent atoms.
  • the heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
  • Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.
  • Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc. .
  • Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridanidyl group, and a triazinyl group.
  • Examples of the partially unsaturated 5-membered heterocyclyl group include pyrrolinyl group, imidazolinyl group (dihydroimidazolinyl group), pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group and the like.
  • Examples of the partially unsaturated 6-membered heterocyclyl group include a thiopyranyl group, a 2H-pyridin-1-yl group, and a 4H-pyridin-1-yl group.
  • Substituents on “C6-10 aryl group” and “3-6 membered heterocyclyl group” include C1-6 alkyl group, hydroxy group, C1-6 alkoxy group, halogeno group, cyano group, nitro group, C1-6 And a haloalkyl group.
  • Examples of the “C6-10 aryloxy group” for X 1 include a phenoxy group and a 1-naphthoxy group.
  • Examples of the substituent on the “C6-10 aryloxy group” include a C1-6 alkyl group, a hydroxy group, a C1-6 alkoxy group, a halogeno group, a cyano group, a nitro group, and a C1-6 haloalkyl group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • X 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an unsubstituted Or a substituted C3-8 cycloalkyl group, a hydroxy group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group C1-6 alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted Or a substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, a halo Amino group is preferably a cyano
  • X 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted Or a substituted C2-6 alkynyloxy group, an unsubstituted or substituted C3-8 cycloalkyloxy group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, an unsubstituted or substituted group An unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted 3-6 membered heterocyclyl group, or an unsubstituted or substituted C6-10 aryloxy group More preferably.
  • X 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-6 alkylthio group, or an unsubstituted group. Or a 3- to 6-membered saturated heterocyclyl group having a substituent.
  • the substituent is preferably a halogeno group or a C3-8 cycloalkyl group.
  • examples of the substituent include a C1-6 alkyl group, a hydroxy group, a C1-6 alkoxy group, a C1-6 alkylthio group, a C6-10 aryl group, and a 3-6 membered heterocyclyl.
  • Group, C1-6 alkyl 3-6 membered heterocyclyl group, halogeno group, cyano group, C3-8 cycloalkyl group, halo C3-8 cycloalkyl group, C1-6 alkyl C3-8 cycloalkyl group and the like are preferable.
  • the substituent is preferably a halogeno group or the like.
  • the substituent is preferably a C1-6 alkyl group and the like.
  • the substituent is preferably a C1-6 alkyl group, a halogeno group, a cyano group, a C1-6 haloalkyl group, or the like.
  • X 1 C1 ⁇ 6 alkyl group, C1 ⁇ 6 haloalkyl group, C1 ⁇ 6 alkoxy group, C1 ⁇ 6 haloalkoxy group, C3 ⁇ 8 cycloalkyl C1 ⁇ 6 alkoxy group, C1 ⁇ 6 alkylthio group, Or, it is preferably a 3- to 6-membered saturated heterocyclyl group.
  • A represents a carbon atom or a nitrogen atom.
  • A is preferably a nitrogen atom.
  • X 2 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, a hydroxy group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group A C1-6 alkoxycarbonyl group, an unsubstituted or substituted amino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl group, Unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl Shows a halogen
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C1-6 alkoxy group”, “C1-7 acyl group” for X 2 ”,“ C1-6 alkoxycarbonyl group ”,“ amino group ”,“ C1-6 alkylthio group ”,“ C1-6 alkylsulfonyl group ”,“ C6-10 aryl group ”,“ 3-6 membered heterocyclyl group ”, Examples of the “halogeno group” and the group having a substituent in these groups are the same as those exemplified for X 1 above.
  • R 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclyl group is shown.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C6-10 aryl group”, and “3-6 members” in R 1
  • R 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, or an unsubstituted or substituted C2-6 alkynyl group. Is preferred.
  • the substituent is preferably a C3-8 cycloalkyl group or a halogeno group.
  • a bond represented by crossed solid lines represents a double bond having stereoisomerism (undefined double stereo bond).
  • the azolyl oxime compound of the present invention or a salt thereof has an E isomer or a Z isomer, or an E isomer, which is a stereoisomer of a double bond derived from the oxime structure in the formula (I). And a mixture of Z isomers.
  • the azolyl oxime compound of the present invention is preferably an azolyl oxime compound represented by formula (II) (hereinafter sometimes referred to as compound (II)).
  • formula (II) X 1 , A, X 2 , n, R 1 and the bond represented by the crossed solid line are as described above.
  • X 11 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl Group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted amino group, unsubstituted or substituted A C1-6 alkylthio group having a group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group .
  • m1 represents the number of X 11 and is an integer from 0 to 2. When m1 is 2 or more, X 11 may be the same as or
  • C1 ⁇ 6 alkyl group in X 11, "C2 ⁇ 6 alkenyl group”, “C2 ⁇ 6 alkynyl group”, “C3 ⁇ 8 cycloalkyl group”, “C1 ⁇ 6 alkoxy group”, "amino group”, “ “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkylsulfonyl group”, “halogeno group” and groups having substituents on these groups include those exemplified in the above X 1 The same thing is mentioned.
  • X 11 is preferably an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogeno group.
  • X 11 is more preferably a halogeno group or a cyano group.
  • m1 is preferably an integer of 0 or 1.
  • Examples of the azolyl oxime compound of the present invention include an azolyl oxime compound represented by the formula (III) (hereinafter sometimes referred to as compound (III)).
  • the salt of the azolyl oxime compound of the present invention is a salt of any of the compounds (I) to (III).
  • the salt is not particularly limited as long as it is an agro-horticulturally acceptable salt.
  • salts of inorganic acids such as hydrochloric acid and sulfuric acid
  • salts of organic acids such as acetic acid and lactic acid
  • salts of alkali metals such as lithium, sodium and potassium
  • salts of alkaline earth metals such as calcium and magnesium
  • iron and copper salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.
  • the salt of the azolyl oxime compound can be obtained by a known method.
  • the azolyloxime compound and the salt thereof of the present invention are not particularly limited by the production method.
  • the azolyl oxime compound and its salt of the present invention can be obtained by known production methods described in Examples and the like.
  • the azolyl oxime compound of the present invention or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”) has an excellent pest control effect such as various agricultural pests and mites that affect plant growth. In addition, it is a highly safe compound due to its low phytotoxicity and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or an acaricide. Furthermore, in recent years, resistance to organophosphates and carbamates has been developed in many pests such as diamondback moth, leafhopper, leafhopper, and aphid, resulting in a lack of efficacy of these drugs. Is desired. The compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains, and further on mite-resistant strains of mites.
  • the compounds of the present invention can be used for a wide variety of filamentous fungi such as fungi belonging to algae (Oomycetes), Ascomycetes, Deuteromycetes, and basidiomycetes. Excellent control of plant pathogens. Therefore, it is useful as an active ingredient of a bactericide.
  • filamentous fungi such as fungi belonging to algae (Oomycetes), Ascomycetes, Deuteromycetes, and basidiomycetes. Excellent control of plant pathogens. Therefore, it is useful as an active ingredient of a bactericide.
  • the pest control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
  • plants to be treated with the pest control agent of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, turf and the like. In that case, each part of these plants can also be processed.
  • each part of the plant include leaves, stems, patterns, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, and the like.
  • GMO genetically modified organisms
  • the pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various agricultural pests and mites, and further to control various phytopathogenic fungi. it can.
  • the pest control agent of the present invention is used in combination or in combination with bactericides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. May be.
  • the compound of the present invention is useful as an active ingredient of an ectoparasite control agent because it is excellent in the control effect of ectoparasites harmful to humans.
  • ectoparasites include ticks, lice and fleas.
  • host animals to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; domestic animals such as cattle, horses, pigs, and sheep; It is done.
  • a bee is mentioned.
  • Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, it infests the back, underarms, lower abdomen, and inner crotch of the host animal and obtains nutrients such as blood and dandruff from the animal.
  • the ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration).
  • a known veterinary technique topical, oral, parenteral or subcutaneous administration
  • it is administered orally to animals by tablet, capsule, feed mixing, etc .; it is administered to animals by immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc .; kneading an ectoparasite-controlling agent into a resin, shaping the kneaded product into an appropriate shape such as a collar or ear tag, and applying it to an animal A method of wearing and administering locally;
  • Formulation 1 wettable powder
  • Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above components were mixed uniformly and finely pulverized to obtain a wettable powder of 40% active ingredient.
  • Formulation 3 Granules
  • Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts or more are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm and active ingredient 5% Get the granules.
  • Formulation 4 Granules
  • Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, water is added and kneaded well, granulated and dried, and 5% active ingredient Get the granules.
  • Formulation 6 Granules
  • Compound of the present invention 5 parts Kaolin 94 parts White carbon 1 part
  • the compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.
  • Formulation 7 Injection
  • Compound of the present invention 0.1-1 part Peanut oil After balance preparation, filter sterilize with a sterilization filter.
  • 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carboxyimidamide was mixed with 3 ml of acetic acid and 6 ml of concentrated hydrochloric acid.
  • An aqueous solution of 0.23 g (3.36 mmol) of sodium nitrite was added dropwise to the mixture at ⁇ 15 ° C. Then, it stirred at room temperature for 4 hours.
  • Ethyl acetate was added thereto and neutralized with an aqueous sodium hydroxide solution. Then, it extracted with ethyl acetate.
  • Example 2 6- (3,3-Dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-isopropyloxime (compound number 1-2) Manufactured.
  • Example 3 6- (3,3-Dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-methyloxime (Compound No. 1-3) Manufactured.
  • 1 H-NMR data of the obtained 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-methyloxime (CDCl 3 / TMS ⁇ (ppm)): 8.82-8.81 (2H, m), 8.09 (1H, s), 7.03 (1H, d), 4.51-4.45 (2H, m), 4.16 (3H, s), 1.74-1.70 (2H , m), 0.99 (9H, s).
  • Example 5 (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-- Isopropyl oxime (Compound No. 1-77) was prepared.
  • Example 6 (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-- Methyl oxime (Compound No. 1-75) was prepared.
  • Table 3 shows the physical property values of the compounds described in Tables 1 and 2 above. “Mp” represents the melting point. “ND” represents a refractive index.
  • Test Example 1 Efficacy Test for Bean Aphids First, 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion containing 5% active ingredient. did. The bean aphid was released on the cowpea where the primary leaves developed. When 1 day had passed since the release, the 1st instar larvae were left and adults were removed. Subsequently, the emulsion was diluted with water to a compound concentration of 125 ppm, and this chemical solution was sprayed on the cowpea. Thereafter, the cowpea was kept in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%.
  • Test Example 2 Efficacy test against brown planthopper
  • the emulsion described in Test Example 1 was diluted with water to a compound concentration of 125 ppm, rice seedlings were immersed in this chemical solution for 10 seconds, and then air-dried. A plastic bag with holes was put on rice seedlings. Ten second instar larvae were released in plastic bags.
  • the rice seedlings were kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release of the insects, the survival of the brown planthopper was examined and the insecticidal rate was determined.
  • two types of (A) drug-sensitive lines and (B) drug-insensitive lines were used as the brown planthopper.
  • the efficacy test was conducted at a compound concentration of 8 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more. 1-1, 1-2, 1-5, 1-7, 1-8, 1-10, 1-13, 1-15, 1-18, 1-20, 1-22, 1-25, 1- 32, 1-33, 1-39, 1-46, 1-47, 1-51, 1-66, 1-68, 1-69, 1-71, 1-72, 1-76, 1-78, 1-80, 1-81, 1-83, 1-86, 1-93, 1-94, 1-111, and 1-121.
  • the efficacy test was conducted at a compound concentration of 2 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more. 1-4, 1-21, 1-26, 1-35, 1-36, 1-65, and 1-77.
  • the efficacy test was conducted at a compound concentration of 31 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more. 1-2, 1-4, 1-5, 1-15, 1-26, 1-46, 1-47, 1-69, 1-80, 1-86, and 1-94.
  • the efficacy test was conducted at a compound concentration of 8 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more. 1-1, 1-21, 1-66, 1-77, and 1-78.
  • Imidacloprid showed an insecticidal rate of 100% at 125 ppm with respect to (A) drug-sensitive line. (B) The insecticidal rate was 50% for the drug-insensitive line.
  • Buprofezin showed a 100% insecticidal rate at 125 ppm with respect to (A) drug-sensitive line. (B) The insecticidal rate was 70% for the drug-insensitive line.
  • Test Example 3 Efficacy test against cotton aphids
  • Adult cotton aphids were released on cucumbers that had been sown in 3-inch pots and 10 days after germination. When 1 day had passed since the release, the 1st instar larvae were left and adults were removed.
  • the emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm, and this chemical solution was sprayed onto the cucumber. Thereafter, the cucumber was kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. After 5 days from spraying, the aphids were examined for life and death, and the insecticidal rate was determined. The said test was done about the chemical
  • All compounds had an insecticidal rate of 80% or more. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1- 13, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-25, 1-26, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-46, 1-47, 1-48, 1- 49, 1-50, 1-51, 1-58, 1-63, 1-65, 1-66, 1-69, 1-71, 1-72, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 1-83, 1-86, 1-87, 1-88, 1-90, 1-91, 1-92, 1-93, 1- 94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-104, 1-106, 1-107, 1-110, 1-111, And 1-121.
  • the efficacy test was conducted at a compound concentration of 31 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more.
  • the efficacy test was conducted at a compound concentration of 8 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more.
  • Test Example 4 Efficacy test against peach aphid
  • the emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm, and the radish was immersed in this chemical solution for 10 seconds. Thereafter, the radish was kept in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%.
  • the mortality of the peach aphid was examined to determine the insecticidal rate. The said test was done about the chemical
  • All compounds had an insecticidal rate of 80% or more.
  • the efficacy test was conducted at a compound concentration of 31 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more. 1-3, 1-10, 1-15, 1-20, 1-21, 1-26, 1-31, 1-46, 1-47, 1-48, 1-58, 1-65, 1- 66, 1-69, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-94, 1-96, 1-97, 1-98, 1-99, 1-104, 1-111, and 1-121.
  • Test Example 5 Efficacy test against leafhopper leaf
  • the emulsion described in Test Example 1 was diluted with water to a compound concentration of 125 ppm, and rice seedlings were immersed in this chemical solution for 10 seconds and allowed to air dry. A plastic bag with a hole was put on the rice seedlings. Ten second instar larvae were released in a plastic bag. Rice seedlings were kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release, the viability of the leafhopper was examined and the insecticidal rate was determined. The said test was done about the chemical
  • the efficacy test was conducted at a compound concentration of 31 ppm.
  • the compounds shown below showed an insecticidal rate of 80% or more.
  • Test Example 6 Efficacy test against tobacco whitefly
  • the emulsion described in Test Example 1 was diluted with water so that the concentration of the compound of the present invention was 125 ppm, and this test chemical solution was sprayed on tomato cut leaves and then air-dried.
  • the leaf was fixed using absorbent cotton so that the leaf surface faced upward.
  • 7 pairs of adult whitefly whitefly type B were released, infested with tomato cut leaves, and kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When two days had passed since the release, adults were examined for viability and the insecticidal rate was determined.
  • the said test was done about the chemical
  • All compounds had an insecticidal rate of 80% or more. 1-5, 1-10, 1-11, 1-15, 1-20, 1-21, 1-22, 1-26, 1-31, 1-32, 1-33, 1-35, 1- 36, 1-37, 1-38, 1-39, 1-40, 1-46, 1-51, 1-65, 1-66, 1-68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-83, 1-88, 1-94, and 1-100.
  • Test Example 8 The emulsion described in Test Example 7 for wheat powdery mildew control was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration would be 100 ppm.
  • Test Example 7 The emulsion described in Test Example 7 for wheat powdery mildew control was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration would be 100 ppm.
  • the said test was done about the chemical
  • Test Example 9 Wheat red rust control test The emulsion described in Test Example 7 was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm. Prepared. Subsequently, the chemical solution was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0 to 1.2 leaf stage). After air-drying the leaves, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated, and wheat seedlings were kept in a 22-25 ° C. greenhouse for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained. The said test was done about the chemical
  • Tomato plague control test The drug solution was prepared by diluting the emulsion described in Test Example 7 with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm. did. Subsequently, the chemical solution was sprayed on tomato seedlings (variety “Regina”, 4-5 leaf stage) grown in an unglazed pot. The leaves were air-dried and then sprayed with a zoospore suspension of Phytophthora infestans, and kept in a temperature-controlled room at 20 ° C. and high humidity for 4 days, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained. The above test was conducted on a chemical solution containing the compound No. 1-6. This compound exhibited a control value of 75% or more.
  • an azolyl oxime compound or a salt thereof which is excellent in insecticidal activity and / or acaricidal activity, excellent in safety and can be synthesized industrially advantageously, and a pest control agent containing this as an active ingredient.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Public Health (AREA)
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Abstract

La présente invention concerne un composé d'azolyloxime représenté par la formule (I) ou un sel de celui-ci. Dans la formule (I), Het représente un cycle hétéroaryle à six chaînons contenant 2 à 3 atomes d'azote en tant qu'atomes structuraux cycliques. X1 est un groupe de substitution sur Het, et représente un groupe alkyle en C1-6 qui peut être non substitué ou peut avoir un groupe de substitution, ou un groupe alcoxy en C1-6 qui peut être non substitué ou peut avoir un groupe de substitution, ou similaire. m indique le nombre de groupes X1, et est un entier de 0 à 3. A représente un atome de carbone ou un atome d'azote. X2 représente un groupe halogène ou un groupe alkyle en C1-6 qui peut être non substitué ou peut avoir un groupe de substitution, ou similaire. n indique le nombre de groupes X2, et est un entier de 0 à 3. R1 représente un groupe alkyle en C1-6 qui peut être non substitué ou peut avoir un groupe de substitution, ou similaire.
PCT/JP2014/051486 2013-01-28 2014-01-24 Composé d'azolyloxime ou sel de celui-ci, agent pesticide, insecticide ou acaricide, désinfectant, et agent antiparasitaire externe WO2014115834A1 (fr)

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TWI652074B (zh) * 2016-08-09 2019-03-01 大日本除蟲菊股份有限公司 防霉劑組成物、防霉用噴霧製品及防霉方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0368559A (ja) * 1989-08-09 1991-03-25 Kumiai Chem Ind Co Ltd オキシム誘導体及び殺虫剤
WO2008006874A1 (fr) * 2006-07-13 2008-01-17 Bayer Cropscience Sa Dérivés fongicides d'hydroximoyle-tétrazole
WO2009130193A1 (fr) * 2008-04-22 2009-10-29 Bayer Cropscience Sa Dérivés d’hétérocycles d’hydroxymoyle fongicides
JP2010138166A (ja) * 2008-11-17 2010-06-24 Ishihara Sangyo Kaisha Ltd 新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
JP2011012088A (ja) * 2010-08-10 2011-01-20 Nippon Soda Co Ltd オキシム化合物またはその塩、ならびに殺菌剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0368559A (ja) * 1989-08-09 1991-03-25 Kumiai Chem Ind Co Ltd オキシム誘導体及び殺虫剤
WO2008006874A1 (fr) * 2006-07-13 2008-01-17 Bayer Cropscience Sa Dérivés fongicides d'hydroximoyle-tétrazole
WO2009130193A1 (fr) * 2008-04-22 2009-10-29 Bayer Cropscience Sa Dérivés d’hétérocycles d’hydroxymoyle fongicides
JP2010138166A (ja) * 2008-11-17 2010-06-24 Ishihara Sangyo Kaisha Ltd 新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
JP2011012088A (ja) * 2010-08-10 2011-01-20 Nippon Soda Co Ltd オキシム化合物またはその塩、ならびに殺菌剤

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