Classifications

• • 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
  • C07D401/02—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 two hetero rings
  • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
  • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
  • A01N41/04—Sulfonic acids; Derivatives thereof
  • A01N41/06—Sulfonic acid amides
• • 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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • 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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
  • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
  • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
  • C07D213/40—Acylated substituent nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/56—Amides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/68—One oxygen atom attached in position 4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/20—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
• • 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
  • C07D417/12—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 chain containing hetero atoms as chain links

Definitions

• the present invention relates to a novel pest control agent. More specifically, the present invention relates to an aryloxyacetamide compound that has excellent acaricidal activity and / or insecticidal activity, is excellent in safety, and can be synthesized advantageously industrially, and a fungicidal agent containing this as an active ingredient. It relates to acaricides and / or insecticides.
• This application claims priority based on Japanese Patent Application No. 2012-29731 filed in Japan on February 14, 2012, the contents of which are incorporated herein by reference.
• Patent Documents 1 to 3 disclose compounds represented by the formulas (A) to (C).
• X 2 represents a hydrogen atom, a halogen atom, a C1-8 alkyl group or the like.
• Y 2 represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, or the like.
• R 6 represents a phenyl group, a cyano group, a C1-4 alkyl group, or the like.
• R 7 represents a hydrogen atom, a C1-4 alkyl group, or the like.
• R 8 and R 9 independently represent a hydrogen atom, a C1-3 alkyl group, or the like.
• R 10 represents a halogen atom or a C1-4 alkyl group.
• X 3 represents a chlorine atom, a bromine atom, or a methyl group.
• Y 3 represents a chlorine atom, a bromine atom, or a methyl group.
• R 11 represents an ethyl group or an n-propyl group.
• R 12 represents an ethyl group.
• one of X 4 and Y 4 represents a nitrogen atom or a nitrogen oxide, and the other represents CR (R represents a hydrogen atom, a halogen atom, etc.), or X 4 And Y 4 both represent a nitrogen atom.
• Z 1 represents a hydrogen atom, a halogen atom or the like.
• R 13 represents an alkyl group, an alkenyl group, or the like.
• R 14 represents a benzyloxymethyl group in which the phenyl ring of the benzyl moiety is optionally substituted with a C1-4 alkoxy group.
• R 15 and R 16 are each independently a hydrogen atom, a C1-3 alkyl group, provided that when both are not hydrogen atoms and both are other than hydrogen atoms, the combined carbon atom sum does not exceed 4.
• R 17 represents a C1-4 alkyl group, a C3-6 cycloalkyl group, or the like.
• the present invention relates to a novel pesticide, among them, an aryloxyacetamide compound or a salt thereof having excellent acaricidal activity and / or insecticidal activity, excellent safety, and can be synthesized industrially advantageously, and It is an object to provide an acaricide and / or an insecticide containing this as an active ingredient.
• an aryloxyacetamide compound having a specific structure or a salt thereof has excellent acaricidal activity and / or insecticidal activity, and has good properties. It has been found that it can be an active ingredient of an acaricide and / or insecticide showing high safety.
• the present invention has been completed based on these findings.
• the present invention includes the following.
• Cy represents a C6-10 aryl group or a 5- to 10-membered heteroaryl group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom.
• X is a substituent on Cy, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2 ⁇ 6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, amino group, unsubstituted or substituted C1-6 alkylamino Group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted A C1-6 alkyls
• n represents the number of X on Cy, and is an integer from 0 to 5.
• Xs may be the same or different.
• X may be connected to each other to form a ring together with a carbon atom or a nitrogen atom on Cy to which X is bonded.
• R 1a 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 C1-6 alkoxy group having a substituent or an unsubstituted or substituted C1-6 alkylthio group is shown.
• R 1b represents a hydrogen atom, 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. Show. Here, R 1a and R 1b may be connected to each other to form a ring together with the carbon atom to which R 1a and R 1b are bonded. Alternatively, R 1a and R 1b may be combined to form an unsubstituted or substituted exomethylene group.
• Z represents an oxygen atom or a sulfur atom.
• Q represents a group represented by formula (II) or formula (III).
• R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group is shown.
• R 3 and R 4 are each independently an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 An alkynyl group, an unsubstituted or substituted C6-10 aryl group, a 5- to 10-membered unsubstituted or substituted group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom A heteroaryl group or a cyano group is shown.
• R 3 and R 4 may be connected to each other to form a ring together with the carbon atom to which R 3 and R 4 are bonded.
• R 5 represents a 5- to 10-membered unsubstituted or substituted heteroaryl group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom.
• R 6 and R 7 are each independently an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 3-8 cycloalkyl group, an unsubstituted or substituted C 2- 6 alkenyl groups, unsubstituted or substituted C2-6 alkynyl groups, unsubstituted or substituted C6-10 aryl groups, or 1 to 4 complex (s) selected from nitrogen, oxygen and sulfur atoms A 5- to 10-membered unsubstituted or substituted heteroaryl group containing an atom is shown.
• R 6 and R 7 may be connected to each other to form a ring together with the sulfur atom to which R 6 and R 7 are bonded. ]]
• a pest control agent containing, as an active ingredient, at least one selected from the aryloxyacetamide compounds and salts thereof according to [1] or [2].
• An acaricide or insecticide containing as an active ingredient at least one selected from the aryloxyacetamide compounds and salts thereof according to [1] or [2].
• An ectoparasite control agent comprising as an active ingredient at least one selected from the aryloxyacetamide compounds and salts thereof according to [1] or [2].
• the aryloxyacetamide compound of the present invention or a salt thereof can control pests that are problematic in crops and hygiene. In particular, mites can be effectively controlled.
• the aryloxyacetamide compound of the present invention is a compound represented by the formula (I).
• the term “unsubstituted” means only a group serving as a mother nucleus. In the present specification, when there is no description of “having a substituent” and only the name of the group serving as the 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.
• “Terms such as“ C1-6 ” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. 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.
• Specific examples of the group that can be a “substituent” include the following groups. Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; 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.
• a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group; Vinyl group, 1-propenyl group, 2-propenyl 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 A C2-6 alkenyl group such as a hexenyl group, a 5-hexenyl group; C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-
• C1-6 alkoxy groups 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; A C6-10 aryl group such as a phenyl group or a naphthyl group; C6-10 aryloxy groups such as phenoxy group and 1-naphthoxy group; A C7-11 aralkyl group such as a benzyl group or a phenethyl group; A C7-11 aralkyloxy group such as a benzyloxy group or a phenethyloxy group; C1-7 acyl groups such as formyl group,
• 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;
• a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group;
• C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group; C
• aminocarbonyl group having no substituent or a substituent such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group;
• Imino C1-6 alkyl groups such as iminomethyl, (1-imino) ethyl, (1-imino) -n-propyl;
• Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
• a mercapto group C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C2-6 alkenylthio groups such as vinylthio group and allylthio group; A C2-6 alkynylthio group such as an ethynylthio group or a propargylthio group; A C6-10 arylthio group such as a phenylthio group or a naphthylthio group; A heteroarylthio group such as a thiazolylthio group or a pyridylthio group; A C7-11 aralkylthio group such as a benzylthio group or a phenethylthio group; (Met
• a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
• a C2-6 alkenylsulfinyl group such as an allylsulfinyl group;
• a C2-6 alkynylsulfinyl group such as a propargylsulfinyl group;
• a C6-10 arylsulfinyl group such as a phenylsulfinyl group; Heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group;
• a C7-11 aralkylsulfinyl group such as a benzylsulfinyl group or a phenethylsulfinyl group
• 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl;
• a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;
• a heteroaryl group of a condensed ring such as an indolyl group, a benzofuryl group, a benzothienyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group;
• Cy represents a C6-10 aryl group or a heteroaryl group.
• the “C6-10 aryl group” may be either a single ring or a polycycle in which the rings are bonded to each other. 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 a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.
• heteroaryl group is a 5- to 10-membered aryl group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms as atoms constituting the ring.
• the heteroaryl group may be either a single ring or a polycyclic ring having condensed rings.
• heteroaryl group examples include the 5-membered heteroaryl group, the 6-membered heteroaryl group and the condensed heteroaryl group exemplified in the above-mentioned “substituent”.
• Cy is phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, indolyl group, benzofuryl group, benzothienyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, A quinoxalinyl group is preferable, and a phenyl group is more preferable.
• X is a substituent on Cy.
• X is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted or A substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or substituted group An unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl Group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C6-1 Aryl group
• n represents the number of X on Cy and is an integer from 0 to 5.
• Xs may be the same or different.
• X may be connected to each other to form a ring together with the carbon atom or nitrogen atom to which X is bonded.
• the “C1-6 alkyl group” in X may be a straight chain or a branched chain.
• 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.
• C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group; 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
• a C1-6 haloalkyl group such as a group, a perfluorohexylethyl group, 2-cycloo
• 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
• C2-6 alkenyloxy C1-6 alkyl groups such as vinyloxymethyl group, allyloxymethyl group, propenyloxymethyl group, butenyloxymethyl group
• Heteroaryloxy C1-6 alkyl groups such as a pyridin-2-yloxymethyl group
• C1-7 acyl group such as formyl group, acetyl group, propionyl group
• C1-7 acyloxy C1-6 alkyl groups
• An alkoxycarbonylamino C1-6 alkyl group; A C7-11 aralkyl group such as a benzyl group or a phenethyl group; A C6-10 arylcarbonylamino C1-6 alkyl group such as a benzoylaminomethyl group; Etc. can be illustrated.
• Examples of the “C3-8 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.
• Examples of the “C2-6 alkenyl group” in X include a vinyl group, 1-propenyl group, 2-propenyl 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.
• the “C2-6 alkynyl group” in X is an 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. can be illustrated.
• C1-6 alkoxy group methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, Examples thereof include s-butoxy group, t-butoxy group, i-hexyloxy group 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 group, 2 And C1-6 haloalkoxy groups such as 1,2,2-trifluoroethoxy group and pentafluoroethoxy group.
• Examples of the “C1-6 alkylamino group” in X include a methylamino group, a dimethylamino group, and a diethylamino group.
• Examples of the “C1-7 acyl group” in X include formyl group, acetyl group, propionyl group, benzoyl group and the like.
• substituted C1-7 acyl group examples include halogen-substituted C1-7 acyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4-chlorobenzoyl group, and the like.
• Examples of the “C1-6 alkoxycarbonyl group” in X include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
• C1-6 alkoxycarbonyl group having a substituent Cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-methylcyclopropylmethoxycarbonyl group, 2,3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group
• a C3-8 cycloalkyl C1-6 alkoxycarbonyl group such as 2-cyclopropylethoxycarbonyl group;
• Fluoromethoxycarbonyl group chloromethoxycarbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2 , 2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, 4-fluorobutoxycarbonyl group, 3,3,3-trifluoropropoxycarbonyl group, 2,2,2 A C1-6 haloalkoxycarbonyl group such as a trifluoro-1-trifluoromethylethoxycarbonyl group or a perfluorohexyloxycarbonyl group; Etc. can be illustrated.
• C1-6 alkylthio group examples include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like.
• substituted C1-6 alkylthio group examples include C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
• C1-6 alkylsulfonyl group examples include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
• substituted C1-6 alkylsulfonyl group examples include C1-6 haloalkylthio groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
• Examples of the “C1-6 alkoxysulfonyl group” in X include a methoxysulfonyl group, an ethoxysulfonyl group, a t-butoxysulfonyl group, and the like.
• Examples of the “C6-10 aryl group” and “heteroaryl group” in X can be the same as those exemplified in the above Cy.
• Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; 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.
• alkyl group 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 cyano group; Etc. can be illustrated.
• Examples of the “hydroxyimino C1-6 alkyl group” in X include a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, a (1-hydroxyimino) propyl group, and the like.
• Examples of the “substituted hydroxyimino C1-6 alkyl group” include methoxyiminomethyl group, (1-methoxyimino) ethyl group, (1-methoxyimino) propyl group, ethoxyiminomethyl group, (1-ethoxyimino) C1-6 alkoxyimino C1-6 alkyl group such as ethyl group, (1-ethoxyimino) propyl group; C3-8 cycloalkyl C1-6 alkoxyimino C1-6 alkyl such as (1-cyclopropylmethoxyimino) ethyl group Examples thereof include C7-11 aralkyloxyimino C1-6 alkyl groups such as benzyloxy
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• Examples of the ring formed together with the carbon atom or nitrogen atom to which X is connected to each other include a cyclopentene ring, cyclohexene ring, 3,4-dihydro-2H-pyran ring, 3,4-dihydro-2H-thiopyran ring, Examples include 3,4-dihydro-2H-thiopyran, 1,1-dioxide ring and the like.
• R 1a represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl.
• R 1a is preferably a C1-6 alkyl group.
• R 1b has a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, or an unsubstituted or substituted group C2-6 alkynyl group.
• R 1a and R 1b may be connected to each other to form a ring together with the carbon atom to which they are bonded.
• Examples of the “ring” formed by the carbon atoms to which R 1a and R 1b are linked to each other are a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and the like.
• Examples of the “exomethylene group having a substituent” formed by R 1a and R 1b together with the carbon atom to which they are bonded include C1-6 alkyl substituted exomethylene such as ethylidene group and isopropylidene group be able to.
• Q represents a group represented by formula (II) or formula (III).
• R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 A -6 alkynyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group;
• “Unsubstituted or substituted C1-6 alkyl group”, “Unsubstituted or substituted C2-6 alkenyl group”, “Unsubstituted or substituted C2-6 alkynyl group” in R 2 , “Unsubstituted or substituted C1-7 acyl group” and “unsubstituted or substituted C1-6 alkoxycarbonyl group” include those exemplified for X above. it can.
• R 3 and R 4 are each independently an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted A C2-6 alkynyl group having a group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heteroaryl group, or a cyano group.
• R 3 and R 4 may be connected to each other to form a ring together with the carbon atom to which they are bonded.
• R 3 and R 4 are preferably C1-6 alkyl groups.
• Examples of the “ring” formed by R 3 and R 4 connected to each other and the carbon atom to which they are bonded include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and an oxirane ring.
• R 5 represents an unsubstituted or substituted heteroaryl group.
• heteroaryl group examples include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc.
• a 5-membered heteroaryl group of A 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;
• a heteroaryl group of a condensed ring such as an indolyl group, a benzofuryl group, a benzothienyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group; Examples thereof include partially unsaturated 5-membered heterocycles such as a pyrrolinyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and a thiazolinyl group.
• the “heteroaryl group” for R 5 is preferably a
• Examples of the substituent on the “heteroaryl group having a substituent” in R 5 include the following substituents.
• Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; 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.
• C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
• a C6-10 aryl group such as a phenyl group or a naphthyl group; 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;
• C6-10 haloaryl group such as 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group; Cyano group; nitro group; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazoly
• R 6 and R 7 are each independently an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or A substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group Indicates.
• R 6 and R 7 may be connected to each other to form a ring together with the sulfur atom to which they are bonded.
• Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; 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.
• alkyl group 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 cyano group; Etc. can be illustrated.
• Examples of the “ring” formed together with the sulfur atom to which R 6 and R 7 are connected to each other include a tetrahydrothiophene ring, a tetrahydrothiopyran ring, an oxathian ring, and the like.
• Z represents an oxygen atom or a sulfur atom. Preferably, it is an oxygen atom.
• Aryloxyacetamide compound represented by formula (IV) Among the aryloxyacetic acid amide compounds according to the present invention, a compound in which Cy in the formula (I) is a phenyl group, R 1b is a hydrogen atom and Q is a group represented by the formula (II), that is, the formula The aryloxyacetamide compound represented by (IV) is preferred.
• R 1a , R 2 to R 5 , X, n, and Z have the same meaning as in formula (I) and formula (II).
• the salt of the aryloxyacetamide compound of the present invention 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
• salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.
• the salt of the aryloxyacetamide compound can be obtained by a known method.
• the amount of compound (2-1) to be used is generally 1-2 mol, preferably 1.0-1.2 mol, per 1 mol of compound (1-1). Although this reaction can be performed in the absence of a base, it is preferably performed in the presence of a base. Examples of the base include pyridine, triethylamine, potassium hydroxide and the like. The amount of the base to be used is generally 1 to 2 mol per 1 mol of compound (1-1).
• the reaction can be carried out in a solvent.
• the solvent is not particularly limited as long as it is inert to the reaction.
• ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
• aromatic hydrocarbon solvents such as toluene, benzene and xylene
• aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
• Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
• Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
• nitrile solvents such as acetonitrile and benzonitrile
• the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 m
• the reaction temperature is in the temperature range from ⁇ 20 ° C. to the boiling point of the solvent used.
• the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
• the subsequent hydrolysis can be carried out according to a conventional method, but is preferably carried out in the presence of a base.
• the base to be used include metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate.
• the amount of the base to be used is generally 1 to 20 mol per 1 mol of compound (3).
• the solvent to be used is not particularly limited as long as it is a solvent that can be mixed with water and is inert to the reaction.
• the thing similar to the solvent illustrated as what is used for manufacture of a compound (2) can be mentioned.
• the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (3).
• the reaction temperature is a temperature range from room temperature to the boiling point of the solvent used. Although the reaction time depends on the reaction scale, it is usually from several minutes to several tens of hours.
• the amount of compound (5) to be used is generally 1 to 2 mol, preferably 1.0 to 1.2 mol, per 1 mol of compound (4).
• This reaction is carried out in a solvent.
• the solvent used is not particularly limited as long as it is inert to the reaction.
• the thing similar to the solvent illustrated as what is used for manufacture of a compound (2) can be mentioned.
• the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (4).
• the compound (5-2) is preferably reacted in the presence of a base. Examples of the base include pyridine, triethylamine, potassium hydroxide and the like.
• the amount of the base to be used is generally 1 to 2 mol per 1 mol of compound (4).
• the reaction temperature is a temperature range from room temperature to the boiling point of the solvent used.
• the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
• the amount of compound (2-2) to be used is generally 1-2 mol, preferably 1.0-1.2 mol, per 1 mol of compound (1-2). Although this reaction can be performed in the absence of a base, it is preferably performed in the presence of a base. Examples of the base include pyridine, triethylamine, potassium hydroxide and the like. The amount of the base to be used is generally 1 to 2 mol per 1 mol of compound (1-2).
• the reaction can be carried out in a solvent.
• the solvent is not particularly limited as long as it is inert to the reaction.
• ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
• aromatic hydrocarbon solvents such as toluene, benzene and xylene
• aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent
• Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane
• Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
• nitrile solvents such as acetonitrile and benzonitrile
• the amount of the solvent to be used is not particularly limited, but is usually 1 to 100 m
• the reaction temperature is in the temperature range from ⁇ 20 ° C. to the boiling point of the solvent used.
• the reaction time is usually several minutes to several tens of hours depending on the reaction scale.
• the desired product can be isolated by purifying by a conventional post-treatment operation and, if desired, known and conventional purification means such as distillation, recrystallization, column chromatography and the like. .
• known and conventional purification means such as distillation, recrystallization, column chromatography and the like.
• the structure of the target product can be identified and confirmed by known analytical means such as IR spectrum, NMR spectrum, mass spectrum, and elemental analysis.
• the aryloxyacetamide compound of the present invention or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”) is effective for controlling various pests (including mites). In particular, it is effective as an acaricide.
• the acaricide containing the compound of the present invention as an active ingredient will be described. Since the compound of the present invention has an action such as an insecticidal insecticide, a larvicidal insecticide, a larvicidal insecticide, an ovicide, etc., it can be used for controlling pests such as mites attached to agricultural crops. In particular, it has excellent control effects on ticks on crops, fruit trees, flowers, and trees.
• Astigmata (Acaridida): (a) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; Tyrophagus spp., Tyrophagus sp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus similis; Others, Acarus siro, Mysticus (Aleuroglyphus cetus)
• Prostigmata mites (Actinedida) (A) mites of the Tetranychidae family, for example of the genus Bryobia spp., Clover spider mite (Bryobia praetiosa), fake clover spider mite (Bryobia rubrioculus); Aid spider mite (Eotetranychus sidani) (Eotetranychus seidu) (Eotetranychus shii) ), White spider mite (Eotetranychus asiaticus), Eotetranychus kankitus; eg Oligonychus mangiferus, Oligonychus perseae, ulosus Spider mite (Oligonychus karamatus), Sugino spider mite (Oligonychus hondoensis), Crimson spider mite (Oligonychus ununguis), Rice spider mite (Oligonychus shinkajii), sugarcane spider mit
• the green spider mite (Sasanychus spp.), The green spider mite (Sasanychus akitanus), the Japanese spider mite (Sasanychus pusillus); ), Spider spider mite (Shizotetranychus longus), Spider spider mite (Shizotetranychus schizopus), Shizotetranychus recki;
• Tenuipalpidae ticks for example, Brevipalpus spp., Brevipalpus lewsulus, Brevipalpus russulus, Brevipalpus obovatus, Penis phoeni );
• Tenuipalpus spp. Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; and others, Dolichotetranychus floridanus;
• Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Carnation mite (Aceria paradianthi), black spider mite (Aceria tiyingi), tulip spider mite (Aceria tulipae), Shibahamaki fushi mite (Aceria zoysiea); for example, Eriophyes spp., Eriophyes chibaensis, For example,
• the acaricide containing the compound of the present invention as an active ingredient is also excellent in controlling the mites parasitizing animals (control of ectoparasites). Mites parasitizing animals that inhabit the back, underarms, lower abdomen, inner thighs, etc. of animals that become hosts (host animals) and obtain nutrients such as blood and dandruff from the animals, and hosts Includes animals that fly to animal backs, buttocks, etc., and obtain nutrients such as blood and dandruff from animals.
• Target host animals include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; Pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); bees (eg, honey bees, Japanese bees); and the like.
• mites (Acari) to be controlled are shown below.
• mite (a) Dermanyssidae mites, such as Dermanyssus gallinae; (b) Mite of the family Mronidsidae (Macronyssidae), for example, Ornithonyssus spp., Ornithonyssus sylviarum, Ornithonyssus bursa, Ornithonyssus bacoti; (c) Mites from the family Laelapidae, for example, Laelaps echidninus, Laelaps jettmari; Tropilaelaps clarae (d) Varroidae mites, such as Varroa spp., Varroa destructor, Varroa jacobsoni, Varroa underwoodi;
• Rhipicephalus evertsi Rhipicephalus sanguineus, Rhipicephalus bursa
• Rhipicephalus appendiculatus Rhipicephalus appendiculatus
• Rhipicephalus appendiculatus Rhipicephalus turanicus
• Rhipicephalus zambeziensis for example Dermacentor marginatus, Dermacentor marginatus, Dermacentor reticulatica (Dermacentor pictus), Dermacentor albipictus, Dermacentor andersoni, Dermacentor Barrier Squirrel (Dermacentor variabilis);
• Astigmata (Acaridida) (a) Mites of the family Psoroptidae, such as Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi; Psoroptes equi; Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis; (b) Scaroptidae mites, such as Sarcoptes spabi, Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis), Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis; for example, Notoedres spp., Notoedres cati; (c) Mites of the family Knemidokoptidae, for example, Knemidokoptes mutans of the genus Knemidokoptes spp .;
• Prostigmata mites Actinedida
• (b) Trombiculidae mites such as the species of the species of the genus Trombicula spp., Trombicula alfreddugesi, Trombicula akamushi;
• the compound of the present invention can be used to control pests such as insects other than mites, hygiene pests, storage shell pests, clothing pests and house pests attached to agricultural crops.
• pests to be controlled are shown below.
• Lepidoptera pests such as Spodoptera litura, Mamestra brassicae, Agrotis ypsilon, Autographa nigrisigna, Plutella xylostella, Adeno hon, mai, hon Homona magnanima), peach sigai (Carposina sasakii), pear tiger squirrel (Grapholitha molesta), mandarin moth (Phyllocnistis citrella), chanohosoga (Caloptilia theivora), kinmonhosoga (Phyllonorycter ringoniella), maiparigai (Lymanttis quaga) suppressalis, Cnaphalocrocis medinalis, European corn borer (Os
• Agrotis spp) Helioverpa
• Agurotisu species clothes moth (Tinea translucens), codling moth (Cydia pomonella), etc. pink bollworm (Pectinophora gossypiella);
• Hemiptera pests for example, Myzus persicae, Aphis gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Riptortus clavatus Acrosternum hilare, Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia tabaci, Silver leaf white genta Stephanitis nashi, Japanese green planthopper (Nilaparvata lugens), Japanese green planthopper (Laodelphax stratella), Japanese white planthopper (Sogatella furcifera), Nephotettix
• the insecticide containing the compound of the present invention as an active ingredient is also excellent in the control effect against pests parasitic on animals (control of ectoparasites). Examples of pests to be controlled are shown below.
• the compounds of the present invention are particularly safe compounds with little phytotoxicity, low toxicity to fish and warm-blooded animals.
• the pest control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
• the pest control agent of the present invention may contain only the compound of the present invention, but may contain a carrier such as a solid carrier, a liquid carrier or a gaseous carrier.
• the pest control agent of the present invention may be obtained by impregnating a substrate such as a porous ceramic plate or a nonwoven fabric with the compound of the present invention.
• a surfactant and other auxiliary agents may be added as necessary.
• the pest control agent of the present invention is in a form that can be taken by general agricultural chemicals, that is, wettable powder, granule, powder, emulsion, aqueous solvent, suspension, granular wettable powder, flowable, microcapsule, aerosol, fumes.
• general agricultural chemicals that is, wettable powder, granule, powder, emulsion, aqueous solvent, suspension, granular wettable powder, flowable, microcapsule, aerosol, fumes.
• an agent a heat transpiration agent, a smoke agent, and an acaricide
• it can be formulated into a form such as a bait agent.
• Additives and carriers used in formulation into solid dosage forms include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay And organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate.
• Solvents used in formulating liquid dosage forms include kerosene, xylene and petroleum-based aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil , Vegetable oil, water and the like.
• gaseous carriers used when formulating into a propellant include butane gas, LPG, dimethyl ether, carbon dioxide gas, and the like.
• food ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, children such as pepper Pest-attracting fragrances such as anti-fouling agents for pets, cheese fragrances, and onion fragrances.
• a surfactant can be added as necessary.
• the surfactant that can be added is not particularly limited.
• alkyl phenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyryl added with polyoxyethylene
• Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.
• the content of the compound of the present invention in the preparation is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
• the wettable powder, emulsion, flowable powder, aqueous solvent and granular wettable powder thus obtained are diluted with water to a predetermined concentration to obtain a solution, suspension or emulsion.
• Granules can be sprayed on plants or soil as they are.
• formulations supplied in the form of oils, aerosols, fumes, poison baits, mite-proof sheets and the like can be used as they are.
• the pest control agent of the present invention when used as an acaricide for controlling mites parasitic on livestock such as cattle and pigs, and pet animals such as dogs and cats, thus, the compound of the present invention can be used in an amount of 0.01 to 1000 mg.
• the acaricide for control can be applied by a known veterinary technique.
• animals such as tablets, capsules, soaking solutions, feed mixing, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.)
• the pest control agent of the present invention is mixed with fungicides, other insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, etc. Or you may use together.
• fungicides, other insecticides / acaricides, nematicides, soil insecticides, and plant growth regulators that can be used in combination with the pest control agent of the present invention are shown below.
• Nicotine receptor agonist / antagonist compounds acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap; flupiradiflon; (6) GABA antagonist compound: (a) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole; (b) Organochlorine-based: camphechlor, chlordane, endosulfan, HCH, ⁇ -HCH, heptachlor, methoxychlor; (7) Macrocyclic lactone insecticides: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomect
• Oxidative phosphorylation inhibitor compounds cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin; (12) molting disruptor: cyromazine; (13) Mixed function oxidase inhibitor compound: piperonyl butoxide; (14) Sodium channel blocker compounds: indoxacarb, metaflumizone; (15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp.
• Latrophilin receptor agonist depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
• Octopaminergic agent Amitraz;
• Ryanodine derivative agonist fulvendiamide, chlorantraniliprole, cyantraliniprol;
• Inhibitors of magnesium-stimulated ATPase thiocyclam, thiosultap, nereistoxin;
• Antifeedant Pymetrozine; (21) Tick growth inhibitor: clofentezin, etoxazole; (22)
• Other compounds Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyrafen, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaal
• Fungicide (1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl; chlorphenazole; (2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin; (3) DMI-bactericidal system: imazalyl, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole
• Phenylamides Benalaxyl, fulleraxyl, metalaxyl, metalaxyl-M, oxadixyl, oflase; benalaxyl-M, cloziracone; (5) Amine-based: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos; (7) Dithiolane type: isopropylthiolane; (8) Carboxamides: benodanyl, boscalid, carboxin, fenfuran, flutolanil, furamethpyr, mepronil, oxycarboxin, pentiopyrad, tifluzamide; (9) Hydroxy- (2-amino) pyrimidine series: bupyrimeto, dimethylolmol, ethylmol;
• AH fungicide (aromatic hydrocarbon) series biphenyl, chloronebu, dichlorane, kintozen, technazen;
• MBI-R system fusaride, pyroxylone, tricyclazole;
• MBI-D system carpropamide, diclocimet, phenoxanyl;
• SBI agent Fenhexamide, Piributicalbu, Turbinafine;
• Phenylurea Pencyclon;
• QiI-bactericides (Qi inhibitors) cyazofamide; amisulbrom, flumeciclos; (21) Benzamide series: Zoxamide; (22) Enopyran uronic system: blastcidin; (23) Hexopyranosyl system: Kasugamycin; Kasugamycin hydrochloride; (24) Glucopyranosyl system: streptomycin, validamycin; validamycin A; (25) Cyanoacetamide series: Simoxanyl; (26) Carbamate
• Phosphate ester phosphorous acid, tolcrofosmethyl, fosetyl; tortofosmethyl;
• Phthalic acid series Teclophthalam;
• Benzotriazine series triazoxide;
• benzenesulfonamide series fursulfamide;
• Pyridazinone Dichromedin;
• CAA disinfectant (carboxylic amide) series dimethomorph, fulmorph, benchavaricarb-isopropyl, iprovaricarb, mandipropamide; variphenate;
• Tetracycline oxytetracycline;
• (36) Thiocarbamate system metasulfocarb;
• Other compounds etridiazole, polyoxin, oxolinic acid, hydroxyisoxazole, octyrinone, silthiofam, diflumetrim, acibenzoral Smethyl, probenazole, thiazinyl, e
• Plant growth regulator Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;
• Tables 1 to 3 show examples of the aryloxyacetamide compounds of the present invention that can be produced by the above-described methods and the like.
• Table 1 shows the substituents in the compound represented by the formula (a).
• Table 2 shows the substituents in the compound represented by the formula (b).
• Table 3 shows the substituents in the compound represented by the formula (c).
• Tables 1 to 3 only show some of the aryloxyacetamide compounds of the present invention that can be produced by the above-described methods. According to the description of the present specification, other compounds not specifically shown in the present specification, that is, those substituted with various groups that do not depart from the spirit and scope of the present invention can be produced and used by the above-described methods. It can be easily understood by those skilled in the art.
• Examples of preparations of the pesticidal composition of the present invention are shown in a few, but the additives and addition ratios are not limited to these examples, and can be varied in a wide range.
• the part in a formulation example shows a weight part. Examples of formulations for agricultural and horticultural use are shown below.
• Formulation Example 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 with 40% active ingredient.
• Formulation Example 2 (Emulsion) Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkyl allyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion containing 30% active ingredient.
• Formulation Example 3 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 Example 4 (Injection) Compound of the present invention 0.1-1 part peanut oil After the balance is prepared, sterilize by filtration using a sterilizing filter.
• Test Example 1 Efficacy test against nymph spider mite (Tetranychus urticae) Ten adult male nymph mite resistant to organophosphates were inoculated on the primary leaves 7 to 10 days after germination of green beans seeded in 3 inch pots. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated 3 days after spraying. Further, it was investigated whether or not eggs laid after 14 days from spraying could develop to adults.
• nymph spider mite Tetranychus urticae
• Test Example 2 Efficacy test against citrus spider mite (Panonychus citri) Eight female citrus spider mites from Kanagawa Prefecture were inoculated on mandarin orange leaves placed in a petri dish. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the mandarin orange using a rotary spray tower. The mandarin orange was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated 3 days after spraying. Furthermore, it was investigated whether the egg laid after 10 days from spraying could develop to an adult. Compound No.
• Test Example 3 Efficacy test against citrus spider mite (Panonychus citri) On a mandarin leaf placed in a petri dish, 8 adult females of acaricide resistant citrus spider mite from Wakayama Prefecture were inoculated. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the mandarin orange using a rotary spray tower. The mandarin orange was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated 3 days after spraying.
• Test Example 4 Efficacy test against Tetranychus kanzawai Ten adult female Kanzawa spider mites from Okayama Prefecture were inoculated on the primary leaves 7 to 10 days after germination of green beans seeded in 3 inch pots. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 500 ppm or 125 ppm, and the diluted solution was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated 3 days after spraying. Further, after 14 days from spraying, it was investigated whether the delivered eggs could develop to adults.
• the above test was performed on an emulsion containing 500 ppm of the compound of Compound No. 1-1.
• the insecticidal rate after 3 days and the insecticidal rate after 14 days were 90% or more.
• the above tests were carried out on emulsions containing 125 ppm each of compounds 2-25, 2-28, 2-29, and 2-30. All compounds had an insecticidal rate after 3 days or an insect
• Test Example 5 Efficacy test against citrus mite (Aculops pelekassi) 20 miticide-resistant citrus mite insects were inoculated on citrus leaves placed in a petri dish. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the mandarin orange using a rotary spray tower. The mandarin orange was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. At 3 days after spraying, adults were examined for viability. Furthermore, it was investigated whether the eggs laid after 10 days from spraying could develop to adults. The above test was conducted on an emulsion containing the compound of Compound No. 1-14. The insecticidal rate after 3 days and the insecticidal rate after 10 days were 90% or more.
• the aryloxyacetamide compound of the present invention or a salt thereof can control pests that are problematic in crops and hygiene. In particular, since mites can be effectively controlled, it is industrially useful.

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