Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
  • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
  • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
  • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic 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
  • C07D401/02—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
  • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
• • 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
  • A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides

Definitions

• the present invention relates to a 1-aryltetrahydropyridazine-3,5-dione derivative or a salt thereof, an insecticide containing the compound as an active ingredient, and a method for using the same.
• Patent Document 1 reports that certain tetrahydropyridazine-3,5-dione derivatives are useful as insecticides. However, these documents neither describe nor suggest the compound having the sulfanyl-aminomethylidene structure of the present invention.
• the present inventors have conducted intensive research to develop new insecticides, especially agricultural and horticultural insecticides, and have discovered that the present invention has a general structure having a sulfanyl-aminomethylidene structure in the 1-aryltetrahydropyridazine-3,5-dione skeleton.
• the present invention was completed based on the discovery that the compound represented by formula (1) or its salts exhibits excellent effects as an insecticide.
• R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 3 - C 6 ) cycloalkyl group; (a8) (C 1 - C 6 ) alkoxy group ;(a9) Substitution having 1 to 3 substituents on the chain, each independently selected from the group consisting of a cyano group, a (C 1 -C 6 ) alkoxy group, and a (C 3 -C 6 ) cycloalkyl group; (C 1 -C 6 ) alkyl group; (a10) 1 to 3 groups each independently selected from the group consisting
• R2 is (b1) an aryl group; (b2) a substituted aryl group having on its ring one or more substituents each independently selected from substituent group A; (b3) a 5- to 10-membered heterocyclic group; or (b4) ) represents a substituted 5- to 10-membered heterocyclic group having one or more substituents independently selected from Substituent Group A on the ring.
• R3 is (c1) Hydrogen atom; (c2) (C 1 -C 6 ) alkyl group; (c3) (C 3 -C 6 ) cycloalkyl group; (c4) (C 1 -C 6 ) alkoxy group; (c5) ( C 1 -C 6 )alkylcarbonyl group; or (c6) (C 1 -C 6 )alkoxycarbonyl group.
• R4 is (d1) (C 1 -C 6 ) alkyl group; (d2) (C 2 -C 6 ) alkenyl group; (d3) (C 2 -C 6 ) alkynyl group; (d4) (C 3 -C 6 ) cyclo Alkyl group; (d5) halo(C 1 -C 6 )alkyl group; (d6) halo(C 2 -C 6 )alkenyl group; (d7) halo(C 2 -C 6 )alkynyl group; (d8) halo( C 3 -C 6 ) cycloalkyl group; (d9) Substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group B; (d10) Substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from C; (d11) N,
• R 3 and R 4 may be bonded to each other to form a ring.
• R5 is (e1) (C 1 -C 6 ) alkyl group; (e2) (C 2 -C 6 ) alkenyl group; (e3) (C 2 -C 6 ) alkynyl group; (e4) (C 3 -C 6 ) cyclo Alkyl group; (e5) halo(C 1 -C 6 )alkyl group; (e6) halo(C 2 -C 6 )alkenyl group; (e7) halo(C 2 -C 6 )alkynyl group; (e8) halo( C 3 -C 6 )cycloalkyl group; (e9) cyano group, (C 1 -C 6 )alkoxy group, (C 3 -C 6 )cycloalkyl group, (C 1 -C 6 )alkylcarbonyl group, (C 3 - C6 ) cycloalkylcarbon
• R 3 and R 5 may be bonded to each other to form a 5- to 6-membered ring.
• Y is an oxygen atom or NR 6 (wherein R 6 is a hydrogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, a (C 3 -C 6 )cycloalkyl group, a halo (C 1 -C 6 ) ) alkyl group, (C 1 -C 6 )alkylcarbonyl group, halo(C 1 -C 6 )alkylcarbonyl group, (C 1 -C 6 )alkoxycarbonyl group, phenylsulfonyl group, or halogen atom, cyano group, and (C 1 -C 6 ) represents a phenylsulfonyl group having 1 to 5 substituents on the ring, each independently selected from the group consisting of alkyl groups.
• Substituent group A is (f1) Halogen atom; (f2) Cyano group; (f3) Nitro group; (f4) Hydroxyl group; (f5) Carboxyl group; (f6) (C 1 - C 6 ) alkyl group; (f7) (C 2 - C 6 ) alkenyl group; (f8) (C 2 -C 6 ) alkynyl group; (f9) (C 1 -C 6 ) alkoxy group; (f10) (C 3 -C 6 ) cycloalkyl group; (f11) ( C1 - C6 ) alkylsulfanyl group; (f12) ( C1 - C6 ) alkylsulfinyl group; (f13) ( C1 - C6 ) alkylsulfonyl group; (f14) halo( C1 - C6 ) alkyl Group; (f15) Halo (C 2 -
• Substituted pyrazolyl group having 1 or 2 independently selected substituents on the ring; (f55) imidazolyl group; (f56) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 - A substituent having on the ring one or two substituents each independently selected from the group consisting of a C 6 ) alkoxy group, a halo(C 1 -C 6 )alkyl group , and a halo(C 1 -C 6 )alkoxy group Imidazolyl group; (f57) Triazolyl group; (f58) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl group, and halo Substituted triazolyl group having on the ring one substituent each independently selected from the group consisting of (C 1
• Substituent group B is (g1) Cyano group; (g2) (C 3 - C 6 ) cycloalkyl group; (g3) (C 1 - C 6 ) alkoxy group; (g4) (C 1 - C 6 ) alkylsulfanyl group; (g5) (C 1 -C 6 )alkylsulfinyl group; (g6) (C 1 -C 6 )alkylsulfonyl group; (g7) halo(C 3 -C 6 )cycloalkyl group; (g8) halo(C 1 -C 6 ) alkoxy group; (g9) halo(C 1 -C 6 )alkylsulfanyl group; (g10) halo(C 1 -C 6 )alkylsulfinyl group; (g11) halo(C 1 -C 6 )alkylsulfonyl group;
• Substituent group C is (h1) Cyano group; (h2) (C 1 -C 6 ) alkyl group; (h3) (C 2 -C 6 ) alkenyl group; (h4) (C 2 -C 6 ) alkynyl group; (h5) (C 3 - C6 ) cycloalkyl group; (h6) ( C1 - C6 ) alkoxy group; (h7) ( C1 - C6 ) alkylsulfanyl group; (h8) ( C1 - C6 ) alkylsulfinyl group; (h9) (C 1 - C 6 ) alkylsulfonyl group; (h10) Halo (C 1 - C 6 ) alkyl group; (h11) Halo (C 3 - C 6 ) cycloalkyl group; (h12) Halo (C 1 -C 6 ) alkoxy group; (h13) halo(C 1 -C 6 )al
• Substituent group D is (i1) halogen atom; (i2) cyano group; (i3) nitro group; (i4) amino group; (i5) hydroxyl group; (i6) carboxyl group; (i7) (C 1 -C 6 ) alkyl group; ( i8) (C 1 -C 6 ) alkoxy group; (i9) (C 3 -C 6 ) cycloalkyl group; (i10) (C 1 -C 6 ) alkylsulfanyl group; (i11) (C 1 -C 6 ) Alkylsulfinyl group; (i12) (C 1 - C 6 ) alkyl sulfonyl group; (i13) Halo (C 1 - C 6 ) alkyl group; (i14) Halo (C 1 - C 6 ) alkoxy group; (i15) Halo (C 3 -C 6 )cycloalkyl group; (i16) halo(C 1 -
• R 2 is a (C 1 -C 6 )alkylsulfonyl group, halo(C 1 -C 6 )alkylsulfonyl group, N-(C 1 -C 6 )alkyl on the atom adjacent to the atom bonded to the tetrahydropyridazine ring.
• R 6 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 )cycloalkyl group, halo(C 1 -C 6 )alkyl group, or (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group
• R 7 is , hydrogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 3 -C 6 ) cycloalkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or halo(C 1 -C 6 )alkylcarbonyl group) is not substituted.
• R 6 is (C 1 -C 6 ) alkyl group, (C 3 -C 6 )cycloalkyl group, halo(C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, or
• R 1 , R 3 , R 4 , R 5 , Y, m, n, substituent groups A, B, C and D are the same as [1],
• R 2 is (b5) Phenyl group;
• (b6) Substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from Substituent Group A;
• (b7) Pyridyl group;
• (b8) From Substituent Group A
• R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a9) Cyano group, (C 1 -C 6 ) alkoxy group and ( Substituted (C 1 -C 6 ) alkyl group having on the chain 1 to 3 substituents each independently selected from the group consisting of C 3 -C 6 ) cycloalkyl group; (a11) (C 1 -C 6 ) Alkylcarbonyl group; (a12) halo(C 1 -C 6 ) alkylcarbonyl group; (a13) (C 3 -C 6 ) cycloalkylcarbonyl group; (a22) (C 1 -C 6 ) alkoxycarbonyl group; (a23) Halo(C 1 -C 6 )alkoxycarbonyl group; (a24) (C 1 -C 6 )alkoxycarbony
• Substituted pyridyl(C 1 -C 6 )alkyl group having 1 to 4 substituents on the ring each independently selected from the group consisting of carbonyl group and halo(C 1 -C 6 )alkylsulfanyl group; (e15 ) Thiazolyl (C 1 -C 6 ) alkyl group; (e16) halogen atom,
• R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a9) Cyano group, (C 1 -C 6 ) alkoxy group and ( Substituted (C 1 -C 6 ) alkyl group having on the chain 1 to 3 substituents each independently selected from the group consisting of C 3 -C 6 ) cycloalkyl group; (a13) (C 3 -C 6 ) Cycloalkylcarbonyl group; (a22) (C 1 - C 6 ) alkoxycarbonyl group; (a24) (C 1 - C 6 ) alkoxy (C 1 - C 6 ) alkoxycarbonyl group; (a35) N-(C 1 - C 6 ) alkylaminocarbonyl group; (a52) (C 1 -C 6 ) alkylsulfonyl group; (a82
• [5] An insecticide characterized by containing the compound or its salts according to any one of [1] to [4] as an active ingredient
• [6] An agricultural and horticultural insecticide characterized by containing the compound or its salts according to any one of [1] to [4] as an active ingredient
• [7] A method for using an insecticide, which comprises applying an effective amount of the insecticide according to [5] or [6] to plants or soil; [8] It relates to the use of the compound or salt thereof according to any one of [1] to [4] as an insecticide.
• the compound of the present invention or its salts has excellent effects as an insecticide. Furthermore, it is effective not only against pests in the agricultural and horticultural fields, but also against pests that infect pet animals such as dogs and cats, and livestock such as cows and sheep.
• halo means a "halogen atom” and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.
• (C 1 -C 6 )alkyl group means, for example, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group.
• tertiary pentyl group neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, Indicates a straight or branched alkyl group having 1 to 6 carbon atoms such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc. .
• (C 2 -C 6 ) alkenyl group means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- Straight chain or branched alkenyl groups having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
• (C 2 -C 6 )alkynyl group means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1 - Straight chain or branched carbon such as propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group, etc. Indicates an alkynyl group having 2 to 6 atoms.
• (C 3 - C 6 ) cycloalkyl group refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and "(C 1 - Examples of “C 6 ) alkoxy group” include methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary Pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, n-hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl Indicates a linear or branched alkoxy group having 1 to 6 carbon atoms,
• Examples of the "(C 1 -C 6 )alkylsulfanyl group” include a methylsulfanyl group, an ethylsulfanyl group, a normal propylsulfanyl group, an isopropylsulfanyl group, a normal butylsulfanyl group, a secondary butylsulfanyl group, a tertiary butylsulfanyl group, Normal pentylsulfanyl group, isopentylsulfanyl group, tertiary pentylsulfanyl group, neopentylsulfanyl group, 2,3-dimethylpropylsulfanyl group, 1-ethylpropylsulfanyl group, 1-methylbutylsulfanyl group, normal hexylsulfanyl group, iso Indicates a linear or branched alkylsulfanyl group having 1 to 6 carbon
• Examples of the "(C 1 -C 6 )alkylsulfinyl group” include a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso It represents a linear or branched
• Examples of the "(C 1 -C 6 )alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso Indicates a linear or branche
• (C 1 -C 6 )alkylcarbonyl group means, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, It refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above-mentioned (C 1 -C 6 ) alkyl group such as a pivaloyl group or a hexanoyl group.
• (C 3 -C 6 )cycloalkylcarbonyl group refers to a cycloalkyl group having the above-mentioned (C 3 -C 6 )cycloalkyl group, such as a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, or a cyclohexylcarbonyl group. Indicates a cycloalkylcarbonyl group having 4 to 7 carbon atoms, such as an alkylcarbonyl group.
• (C 1 -C 6 )alkylcarbonylamino group means, for example, acetylamino group, propanoylamino group, butanoylamino group, 2-methylpropanoylamino group, pentanoylamino group, 2-methylbutanoyl
• An alkylcarbonylamino group having 2 to 7 carbon atoms such as an alkylcarbonylamino group having the above-mentioned (C 1 -C 6 ) alkyl group such as an amino group, 3-methylbutanoylamino group, pivaloylamino group, hexanoylamino group, etc. shows.
• Examples of the "(C 1 -C 6 )alkylsulfonylamino group” include a methylsulfonylamino group, an ethylsulfonylamino group, a normal propylsulfonylamino group, an isopropylsulfonylamino group, a normal butylsulfonylamino group, and a secondary butylsulfonylamino group.
• tertiary butylsulfonylamino group normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group , 1-methylbutylsulfonylamino group, n-hexylsulfonylamino group, isohexylsulfonylamino group, 1,1,2-trimethylpropylsulfonylamino group, etc.
• linear or branched alkyl having 1 to 6 carbon atoms Indicates a sulfonylamino group.
• N-(C 1 -C 6 )alkylaminocarbonyl group means, for example, N-methylaminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, N- -Normal butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiary butylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-isopentylaminocarbonyl group, N-tertiary Contains a linear or branched alkyl group having 1 to 6 carbon atoms, such as a liepentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexylaminocarbonyl group, and N-isohexylaminocarbonyl group.
• N,N-di(C 1 -C 6 )alkylaminocarbonyl group examples include N,N-dimethylaminocarbonyl group, N,N-diethylaminocarbonyl group, and N,N-dinormalpropylaminocarbonyl group.
• N,N-diisopropylaminocarbonyl group N,N-dinormalbutylaminocarbonyl group, N,N-dise-butylaminocarbonyl group, N,N-ditertiarybutylaminocarbonyl group, N-methyl-N-ethyl Aminocarbonyl group, N-methyl-N-normalpropylaminocarbonyl group, N-methyl-N-isopropylaminocarbonyl group, N-methyl-N-normalbutylaminocarbonyl group, N-methyl-N-secondary butylaminocarbonyl group , N-methyl-N-tert-butylaminocarbonyl group, N-methyl-N-normalpentylaminocarbonyl group, N-methyl-N-isopentylaminocarbonyl group, N-methyl-N-tert-pentylaminocarbonyl group , N-methyl-N-neopentylaminocarbonyl group
• (C 1 -C 6 )alkoxycarbonyl group means, for example, methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, It refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C 1 -C 6 ) alkoxy group, such as a tert-butoxycarbonyl group or a pentyloxycarbonyl group.
• N-(C 1 -C 6 )alkylaminosulfonyl group examples include N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normalpropylaminosulfonyl group, N-isopropylaminosulfonyl group, N- -Normal butylaminosulfonyl group, N-Secondary butylaminosulfonyl group, N-Tertiary butylaminosulfonyl group, N-Normalpentylaminosulfonyl group, N-Isopentylaminosulfonyl group, N-Tertiary pentylaminosulfonyl group, N -Neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1-ethylpropyl)aminosulfonyl group,
• N,N-di(C 1 -C 6 )alkylaminosulfonyl group examples include N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, and N,N-dinormalpropylaminosulfonyl group.
• N,N-diisopropylaminosulfonyl group N,N-di-n-butylaminosulfonyl group, N,N-dise-butylaminosulfonyl group, N,N-ditertiarybutylaminosulfonyl group, N-methyl-N-ethyl Aminosulfonyl group, N-methyl-N-normalpropylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normalbutylaminosulfonyl group, N-methyl-N-secondary butylaminosulfonyl group , N-methyl-N-tert-butylaminosulfonyl group, N-methyl-N-normalpentylaminosulfonyl group, N-methyl-N-isopentylaminosulfonyl group, N-methyl-N-tert-pent
• Halo(C 1 -C 6 )alkyl group "Halo(C 2 -C 6 )alkenyl group”, “Halo(C 2 -C 6 )alkynyl group”, “Halo(C 1 -C 6 ) alkyl group”, respectively.
• alkoxy group "halo(C 1 -C 6 )alkylsulfanyl group”, “halo(C 1 -C 6 )alkylsulfinyl group”, “halo(C 1 -C 6 )alkylsulfonyl group”, “halo(C 6 )alkylsulfonyl group” 3 -C 6 )cycloalkyl group", "Halo(C 1 -C 6 )alkylcarbonylamino group”, “Halo(C 1 -C 6 )alkylsulfonylamino group", “N-halo(C 1 -C 6 ) ) alkylaminocarbonyl group” etc.
• aryl group refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a phenyl group, 1-naphthyl group, and 2-naphthyl group.
• a “5- to 10-membered heterocyclic group” refers to a 5- or 6-membered monocyclic aromatic ring containing 1 to 4 heteroatoms selected from oxygen atoms, sulfur atoms, and nitrogen atoms in addition to carbon atoms as ring constituent atoms.
• group heterocyclic group an aromatic fused heterocyclic group in which the monocyclic aromatic heterocycle is fused with a benzene ring or a monocyclic aromatic ring, a 4- to 6-membered monocyclic non-aromatic heterocyclic group, or Examples include non-aromatic fused heterocyclic groups in which a monocyclic non-aromatic heterocycle is fused to a benzene ring or a monocyclic aromatic ring.
• the ring atoms of the 5- to 10-membered heterocyclic group may be oxidized with an oxo group.
• Examples of the "monocyclic aromatic heterocyclic group” include furyl group, thienyl group, pyridyl group, 2-oxopyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, and thiazolyl group. , isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group (e.g. 1,3,4-oxadiazolyl group, 1,2,4-oxadiazolyl group), thiadiazolyl group (e.g.
• aromatic fused heterocyclic group include quinolinyl group, isoquinolinyl group, quinazolinyl group, quinoxalinyl group, cinnolinyl group, phthalazinyl group, naphthyridinyl group, benzofuranyl group, benzothienyl group, benzoxazolyl group.
• benzisoxazolyl group benzothiazolyl group, benzisothiazolyl group, benzimidazolyl group, benzotriazolyl group, indolyl group, isoindolyl group, indazolyl group, furopyridyl group, thienopyridyl group, pyrrolopyridyl group (for example, pyrrolo[1, 2-a]pyridyl group, pyrrolo[2,3-b]pyridyl group), oxazolopyridyl group (e.g., oxazolo[3,2-a]pyridyl group, oxazolo[5,4-b]pyridyl group, oxazolo[ 4,5-b]pyridyl group), isoxazolopyridyl group (e.g., isoxazolo[2,3-a]pyridyl group, isoxazolo[4,5-b]
• imidazo[1,2-a]pyridyl group) imidazo[4,5-b]pyridyl group
• pyrazolopyridyl group e.g., pyrazolo[1,5-a]pyridyl group, pyrazolo[3,4-a]pyridyl group, pyrazolo[4,3-a] pyridyl group
• indolizinyl group triazolopyridyl group (e.g.
• [1,2,4]triazolo[1,5-a]pyridyl group) triazolopyrimidinyl group, pyrrolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrimidinyl group, imidazo Examples include pyrazinyl group, pyrazolopyrimidinyl group, pyrazolothienyl group, and pyrazolotriazinyl group.
• Examples of the "monocyclic non-aromatic heterocyclic group” include oxetanyl group, thietanyl group, azetidinyl group, pyrrolidinyl group, pyrrolidinyl-2-one group, piperidinyl group, morpholinyl group, thiomorpholinyl group, piperazinyl group, hexamethylene group, etc.
• Examples include pinyl group, tetrahydrobenzofuranyl group, chromenyl group, dihydroquinolinyl group, tetrahydroquinolinyl group, dihydroisoquinolinyl group, tetrahydroisoquinolinyl group, dihydrophthalazinyl group, and the like.
• R 3 and R 4 may be bonded to each other to form a ring.
• the "ring" is a ring formed by bonding a group obtained by removing an arbitrary hydrogen atom from R 3 and a group obtained by removing an arbitrary hydrogen atom from R 4 .
• R 3 is an ethyl group and R 4 is a normal propyl group, and there is a group obtained by removing the hydrogen atom at the tip from the ethyl group in R 3 , and a group obtained by removing the hydrogen atom at the tip from the normal propyl group in R 4.
• piperidine is formed.
• Examples of the "ring” include 3- to 7-membered nitrogen-containing heterocycles such as aziridine, azetidine, pyrrolidine, piperidine, homopiperidine, piperazine, homopiperazine, morpholine, and homomorpholine.
• the nitrogen-containing heterocycle may be fused with a benzene ring.
• the nitrogen-containing heterocycle and benzene ring are substituted with 1 to 6 substituents selected from the group consisting of a halogen atom, a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, etc. You can leave it there.
• R 3 and R 5 may be bonded to each other to form a 5- to 6-membered ring.
• the "5- to 6-membered ring" is a ring formed by bonding a group obtained by removing an arbitrary hydrogen atom from R 3 and a group obtained by removing an arbitrary hydrogen atom from R 5 .
• R 3 is an acetyl group and R 5 is a methyl group, and the acetyl group of R 3 with the hydrogen atom removed and the methyl group of R 5 with the hydrogen atom removed, then 1 , 3-thiazolidin-4-one is formed.
• R 3 and R 5 When one of R 3 and R 5 is a hydrogen atom, the other group may be directly bonded to the nitrogen atom to which R 3 is bonded or to the sulfur atom to which R 5 is bonded to form a 5- to 6-membered ring.
• the "5- to 6-membered ring” includes 1,3-thiazolidine, hexahydro-1,3-thiazine, 1,3-thiazolidin-4-one, 1,3-thiazolidin-5-one, hexahydro-1,3 -thiazin-4-one, hexahydro-1,3-thiazin-6-one and the like.
• Examples of the salts of the compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate, With organic acid salts such as methanesulfonate, benzenesulfonate, paratoluenesulfonate, inorganic or organic bases such as sodium ion, potassium ion, calcium ion, cesium ion, magnesium ion, ammonium ion, trimethylammonium, etc. Examples include salts.
• the compound represented by the general formula (1) of the present invention and its salts may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. In some cases, optical isomers exist, and the present invention includes all optical isomers and mixtures containing them in arbitrary proportions.
• the compound represented by the general formula (1) of the present invention and its salts have two or more types of geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in the structural formula. However, the present invention also includes all geometric isomers and mixtures containing them in arbitrary proportions.
• the compound represented by the general formula (1) of the present invention and its salts may have a plurality of tautomers, but the present invention covers each tautomer and their arbitrary proportions. It also includes all mixtures included.
• R 1 is the above (a1), (a2), (a6), (a9), (a11), (a12), (a13), (a22), (a23), (a24), (a35), (a41), (a52), (a69), (a76), (a82), (a84), (a85), (a86), or (a87) groups are preferred;
• the above groups (a1), (a2), (a6), (a9), (a13), (a22), (a24), (a35), (a52), (a82), or (a85') are More preferred.
• R 2 is the above (b5), (b6), (b7), (b8), (b9), (b10), (b11), (b12), (b13), (b14), (b15), (b16), (b17), (b18), (b19), (b20), (b21), (b22), (b23), (b24), (b25), (b26 ), (b27), (b28), (b29), (b30), (b31), (b32), (b33), (b34), (b35), (b36), (b37), (b38), (b39), (b40), (b41), (b42), (b43), (b44), (b45), (b46), (b47), (b48), (b49), (b50), (b51 ), (b52), (b53), (b54), (b55), (b56), (b57), (b58), (b59), (b60), (b61), (b62), (b63), (b64), (b65
• R 3 is preferably the above group (c1), (c2), (c3), (c5), or (c6), The above groups (c1), (c2), (c5), or (c6) are more preferred.
• R 4 is the above (d1), (d3), (d4), (d5), (d9), (d10), (d17), (d18), (d19), (d20), (d21), (d22), (d23), (d24), (d25), (d26), (d43), or (d44) groups are preferred;
• the above groups (d4), (d17), (d18), (d20), or (d44) are more preferred.
• R 5 is the above (e1), (e2), (e3), (e4), (e5), (e6), (e9), (e11), (e12), (e13), (e14), (e15), (e16), (e17), (e18), (e19), (e20), (e21), (e22), (e23), (e24), (e25 ), (e26), (e27), (e28), (e29), (e30), (e31), (e32), (e33), (e34), (e35), or (e36) groups are preferred.
• substituent group A includes the above (f1), (f2), (f6), (f9), (f10), (f11), (f14), (f17), (f22 ), (f59), (f60), and (f94), It is more preferable to consist of the above groups (f1), (f2), (f6), (f9), (f11), (f14), and (f94).
• substituent group B preferably consists of the above groups (g1), (g2), (g3), and (g4).
• substituent group C preferably consists of the above groups (h1), (h2), and (h10).
• the substituent group D includes the above (i1), (i2), (i7), (i8), (i9), (i10), (i13), (i14), (i15 ), (i19), and (i25), It is more preferable to consist of the above groups (i1), (i2), (i7), (i8), (i10), (i14), and (i19).
• R 2 , R 4 and R 5 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, iodine, a (C 1 -C 6 ) alkylcarbonyloxy group, or a (C 1 -C 6 ) alkoxycarbonyloxy group.
• step [a] By reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent, the general formula (1 A compound represented by -1) can be produced.
• bases examples include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, sodium ethoxide, potassium t- Alkali metal salts of alcohols such as butoxide, inorganic bases such as carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, organic bases such as triethylamine, pyridine, N,N-dimethyl-4-aminopyridine, DBU, etc.
• the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (2).
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Inert solvents such as cyclic or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide,
• Examples include aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. They can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
• reaction temperature in this reaction is usually within the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. All you have to do is choose.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• step [b] By hydrolyzing a compound represented by general formula (1-1) in the presence or absence of an acid and an inert solvent, a compound represented by general formula (1-2) is obtained. compounds can be manufactured.
• acids that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and paratoluene.
• inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid
• organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and paratoluene.
• sulfonic acids such as sulfonic acid, phosphoric acid, etc.
• the amount used is appropriately selected from the range of 0.01 times mole to 10 times mole relative to the compound represented by general formula (1-1).
• the acid can also be used as a solvent.
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, etc.
• Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene
• chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, N,N -Amides such as dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and inert solvents such as polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more.
• the amount of the inert solvent to be used is not particularly limited as long as it dissolves the reaction reagent, but it may be appropriately selected from the range of 0.5 L to 100 L per mol of the compound represented by the general formula (1-1). good. Furthermore, when the acid is used as a solvent, it is not necessary to use a solvent.
• the reaction temperature can be carried out in the range from room temperature to the boiling point of the acid or inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be appropriately selected from the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• R 1' is a (C 1 -C 6 )alkyl group, (C 2 -C 6 )alkenyl group, (C 2 -C 6 )alkynyl group, (C 3 -C 6 )cycloalkyl group, halo (C 1 -C 6 ) alkyl group, halo (C 3 -C 6 ) cycloalkyl group, (C 1 -C 6 ) alkoxy group, cyano group, (C 1 -C 6 ) alkoxy group and (C 3 -C 6 ) cyclo Substituted (C 1 -C 6 ) alkyl groups, cyano groups, (C 1 -C 6 ) alkyl groups and (C Substituted (C 3 -C 6 )cycloalkyl group having 1 to 3 substituents each independently selected from the group consisting of 1 -C 6
• L represents, for example, a leaving group such as chlorine, bromine, iodine, a (C 1 -C 6 ) alkylcarbonyloxy group, or a (C 1 -C 6 ) alkoxycarbonyloxy group.
• step [c] By reacting the compound represented by general formula (1-3) with an oxidizing agent in an inert solvent, the compound represented by general formula (1-4) of the present invention is prepared. can be manufactured.
• oxidizing agent used in this reaction examples include peroxides such as hydrogen peroxide, perbenzoic acid, and metachloroperbenzoic acid.
• the amount can be appropriately selected from the range of 1 to 5 times the mole of the compound represented by 3).
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonized solvents such as benzene, toluene, and xylene.
• Hydrogen, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
• organic acids N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water, and other polar solvents, and these inert solvents can be used alone or in combination. Two or more types can be mixed and used.
• the amount of the inert solvent to be used is not particularly limited as long as it dissolves the reaction reagent, but it may be appropriately selected from the range of 0.5 L to 100 L per 1 mole of the compound represented by the general formula (1-3). good.
• the reaction temperature in this reaction may be appropriately selected from the range of -10°C to the reflux temperature of the inert solvent used.
• the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from a range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• Manufacturing method 3 The compound represented by the general formula (1-5) of the present invention can be produced from the compound represented by the general formula (1-3) of the present invention by the following step [d].
• step [d] By reacting the compound represented by the general formula (1-3) with an oxidizing agent and the compound represented by the general formula (5) in an inert solvent, the general formula A compound represented by (1-5) can be produced.
• oxidizing agent used in this reaction examples include bisacetoxyiodobenzene, N-chlorosuccinimide, N-bromosuccinimide, etc.
• the amount of these oxidizing agents used is expressed by the general formula (1-3). The amount can be appropriately selected from the range of 1 to 5 times the mole of the compound to be used.
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonized solvents such as benzene, toluene, and xylene.
• Hydrogen, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
• organic acids N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water, and other polar solvents, and these inert solvents can be used alone or in combination. Two or more types can be used in combination.
• the amount of the inert solvent to be used is not particularly limited as long as it dissolves the reaction reagent, but it may be appropriately selected from the range of 0.5 L to 100 L per 1 mole of the compound represented by the general formula (1-3). good.
• reaction temperature in this reaction may be appropriately selected from the range of -10°C to the reflux temperature of the inert solvent used.
• the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from a range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• Manufacturing method 4 The compound represented by the general formula (1-5) of the present invention can be produced from the compound represented by the general formula (1-3) of the present invention by the following step [e].
• step [e] The compound represented by the general formula (1-3) is reacted with the compound represented by the general formula (6) in an inert solvent. A compound represented by 5) can be produced.
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonized solvents such as benzene, toluene, and xylene.
• Hydrogen, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
• organic acids N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, and polar substances such as water.
• examples include solvents, and these inert solvents can be used alone or in combination of two or more.
• the amount of the inert solvent to be used is not particularly limited as long as it dissolves the reaction reagent, but it may be appropriately selected from the range of 0.5 L to 100 L per 1 mole of the compound represented by the general formula (1-3). good.
• reaction temperature in this reaction may be appropriately selected from the range of 0° C. to the reflux temperature of the inert solvent used.
• the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from a range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• Manufacturing method 5 The compound represented by the general formula (1-6) of the present invention can be produced from the compound represented by the general formula (1-3) of the present invention by the following step [f].
• step [f] By reacting the compound represented by the general formula (1-3) with an oxidizing agent and ammonium carbonate (7) in an inert solvent, the compound represented by the general formula (1-6) of the present invention is produced.
• a compound represented by can be produced.
• oxidizing agent used in this reaction examples include bisacetoxyiodobenzene, N-chlorosuccinimide, N-bromosuccinimide, etc.
• the amounts of these oxidizing agents used are expressed by the general formula (1-3). The amount can be appropriately selected from the range of 1 to 5 times the mole of the compound to be used.
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonized solvents such as benzene, toluene, and xylene.
• Hydrogen, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
• organic acids N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, and polar substances such as water.
• examples include solvents, and these inert solvents can be used alone or in combination of two or more.
• the amount of the inert solvent to be used is not particularly limited as long as it dissolves the reaction reagent, but it may be appropriately selected from the range of 0.5 L to 100 L per 1 mole of the compound represented by the general formula (1-3). good.
• reaction temperature in this reaction may be appropriately selected from the range of 0° C. to the reflux temperature of the inert solvent used.
• the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from a range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• R 2 , R 4 and R 5 are the same as above.
• Q represents an oxygen atom or a sulfur atom.
• R 1a is a (C 1 -C 6 ) alkyl group, a halo (C 1 -C 6 ) alkyl group, a (C 2 -C 6 ) alkenyl group, a (C 2 -C 6 )alkynyl group, a (C 3 -C 6 ) Cycloalkyl group, (C 1 -C 6 ) alkoxy group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (C 1 -C 6 )alkylsulfanyl (C 1 -C 6 ) 1 to 3 substituents each independently selected from the group consisting of an alkyl group, a phenyl (C 1 -C 6 ) alkyl group, a halogen atom, a cyano group, a nitro group, and
• step [g] The present invention can be carried out by reacting the compound represented by the general formula (1-2) of the present invention with the compound represented by the general formula (8) in the presence of a base and an inert solvent.
• a compound represented by the general formula (1-7) can be produced.
• bases examples include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.
• alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
• Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine, and the amount used is determined according to the general formula. It is usually used in an amount of 1 to 10 times the mole of the compound represented by (1-2).
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Inert solvents such as cyclic or cyclic ethers, nitriles such as acetonitrile and propionitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.
• Examples include aprotic polar solvents such as methanol, ethanol, propanol, butanol, alcohols such as 2-propanol, and these inert solvents can be used alone or in combination of two or more.
• the amount used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (1-2).
• reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• Manufacturing method 7 The compound represented by the general formula (1-3) of the present invention can be produced from the compound represented by the general formula (1-2) of the present invention by the following step [a]. Note that the reaction conditions are the same as described above.
• R 1' , R 2 , R 4 and R 5 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, iodine, a (C 1 -C 6 ) alkylcarbonyloxy group, or a (C 1 -C 6 ) alkoxycarbonyloxy group.
• the compound represented by the general formula (2) which is a starting material, is produced by the following manufacturing method, that is, from the compound represented by the general formula (9), the following steps [h], [i], [j], [k] and [g]. Note that the reaction conditions for [g] are the same as above. Moreover, the compound represented by general formula (13) can also be manufactured according to the method described in International Publication No. 2021/261563 pamphlet.
• R 2 and R 4 are the same as above.
• R and R' represent, for example, a (C 1 -C 6 ) alkyl group such as a methyl group or an ethyl group.
• step [h] By condensing a compound represented by general formula (9) and a compound represented by general formula (10) by an amidation method commonly used in organic synthesis, the general formula ( A compound represented by 11) can be produced.
• a compound represented by general formula (12) can be manufactured by performing a cyclization reaction on a compound represented by general formula (11) in the presence of a base and an inert solvent. can.
• Examples of the base used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.
• Alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate,
• alkali metal hydrides such as sodium hydride, potassium hydride
• carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate
• Examples include acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and diisopropylethylamine, and the amount used is represented by general formula (11). It is usually used in an amount of 1 to 10 times the mole of the compound.
• the inert solvent used in this reaction may be one that does not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2 Examples include alcohols such as -propanol, and these inert solvents can be used alone or in a mixture of two or more. The amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (11).
• the reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
• a compound represented by general formula (13) can be manufactured by reacting a compound represented by general formula (12) under heating conditions in the presence of an inert solvent.
• the inert solvent used in this reaction may be one that does not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
• inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran
• acetonitrile propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide
• aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2
• examples include alcohols such as -propanol, water, etc., and these inert solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (12).
• the reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• step [k] By reacting the compound represented by general formula (13) with the compound represented by ditertiary butyl dicarbonate (6) in the presence of a base and an inert solvent, the general formula (15 ) can be produced.
• bases examples include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, sodium ethoxide, potassium t- Alkali metal salts of alcohols such as butoxide, inorganic bases such as carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, organic bases such as triethylamine, pyridine, N,N-dimethyl-4-aminopyridine, DBU, etc.
• the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (13).
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Inert solvents such as cyclic or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide,
• Examples include aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. They can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (13).
• reaction temperature in this reaction is usually within the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. All you have to do is choose.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• the compound represented by the general formula (4) which is a starting material, can be manufactured by the following manufacturing method, that is, from the compound represented by the general formula (13), by the following steps [a] and [g]. Note that the reaction conditions for [a] and [g] are the same as described above.
• R 1' , R 2 and R 4 are the same as above.
• L represents, for example, a leaving group such as chlorine, bromine, iodine, a (C 1 -C 6 ) alkylcarbonyloxy group, or a (C 1 -C 6 ) alkoxycarbonyloxy group.
• Manufacturing method of starting materials 3 The compound represented by general formula (9) can be manufactured by the following manufacturing method, that is, from the compound represented by general formula (19), by the following steps [l] and [m].
• R 2 and R are the same as above.
• L' and L'' represent, for example, leaving groups such as fluorine, chlorine, bromine, and iodine.
• step [l] By reacting a compound represented by general formula (19) with hydrazine monohydrate represented by formula (20) in the presence of an inert solvent, a compound represented by general formula (21) is produced. Compounds can be produced.
• the inert solvent used in this reaction may be one that does not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, methanol, ethanol, and propanol.
• Examples include alcohols such as , butanol, and 2-propanol, and these inert solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (19).
• reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• step [m] By reacting a compound represented by general formula (21) with a compound represented by general formula (22) in the presence of a base and an inert solvent, a compound represented by general formula (9) is prepared. Compounds can be produced. In addition, according to the method described in International Publication No.
• Examples of the base used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide. alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
• Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine. It is usually used in an amount of 1 to 10 times the mole of the compound represented by 21).
• the inert solvent used in this reaction may be one that does not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, acetonitrile, propionitrile and aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolidinone.
• the active solvents can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (21).
• reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• Manufacturing method of starting materials 4 The compound represented by general formula (9) can also be manufactured by the following manufacturing method, that is, from the compound represented by general formula (19), by the following step [n].
• step [n] By reacting a compound represented by general formula (19) with a compound represented by general formula (23) in the presence of a base and an inert solvent, a compound represented by general formula (9) is prepared. Compounds can be produced. In addition, according to the method described in International Publication No.
• bases examples include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.
• alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
• Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine, and the amount used is determined according to the general formula. It is usually used in an amount of 1 to 10 times the mole of the compound represented by (19).
• Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
• Inert solvents such as cyclic or cyclic ethers, nitriles such as acetonitrile and propionitrile, esters such as methyl acetate, ketones such as acetone and methyl ethyl ketone, N,N-dimethylformamide, N,N-dimethylacetamide,
• Examples include aprotic polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, and alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol. They can be used alone or in combination of two or more.
• the amount to be used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (19).
• reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• the compound represented by general formula (9) can also be manufactured by the following manufacturing method, ie, from the compound represented by general formula (24), by the following steps [m] and [o]. Note that the reaction conditions for [m] are the same as described above.
• step [o] The compound represented by general formula (9) is reacted with sodium nitrite in the presence of an acid, and then reduced with a reducing agent. can be manufactured.
• acids that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, and organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, and benzoic acid.
• the amount may be appropriately selected from the range of 0.01 to 10 times the mole of the compound represented by formula (25), but the acid can also be used as a solvent.
• Examples of the reducing agent used in this reaction include sodium sulfite, tin chloride, etc., and the amount used is usually 1.0 times to 1.0 times the mole of the compound represented by general formula (25). It may be used by appropriately selecting from a range of 10 times the mole.
• the reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc. Alternatively, it can be used in the next step without isolation.
• the agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention are various agricultural, forestry, horticultural, and grain storage pests that damage paddy rice, fruit trees, vegetables, other crops, and flowers. It is suitable for controlling pests such as sanitary pests, nematodes, etc.
• agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have physical properties suitable for various labor-saving application methods, systemic transfer activity, and suitable soil compatibility. Excellent environmental safety such as persistence.
• agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have no effect on natural enemies, useful insects such as the European honey bee and bumblebee, and environmental organisms such as midges. Less is.
• Lepidoptera lepidoptera
• Lepidoptera include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, and American white flycatcher.
• Adoxophyes orana) Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Biston robustum Bucculatrix pyrivorella), Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis ), Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia
• Hemipteran pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc.
• Aeschynteles maculatus Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissusleuc opterus), Iseria Icerya purchasi, Piezodorus hybneri, Lagynotomus elongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae, Stariodes i wasakii) , Aspidiotus destructor, Taylorilygus pallidulus, Myzusmumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum, Anacan
• Kankitsu Kai Garamushi (Andaspis Kashicola), Coccus Pseudomagnoliarum, Kanesuko Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphor ae), spider Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaula caspis pentagona ), Pulvinaria kuwacola, A
• apple oyster scale insect Lepidosaphes ulmi
• apple oyster louse Psylla mali
• apple black snail Heterocordylus flavipes
• apple knoll aphid Myzus malisuctus
• apple aphid Aphidonuguis mali
• apple leafhopper Orientus ishidai
• apple Examples include green aphid (Ovatus malicolens), apple boll beetle (Eriosoma lanigerum), ruby beetle (Ceroplastes rubens), and cotton aphid (Aphis gossypii).
• pests of the order Coleoptera include Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, and alfalfa weevil.
• Diptera pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and Chlorops oryzae.
• Hydrellia sasakii Agromyza oryzae
• Hydrellia griseola Ophiomyia phaseoli
• Dacus cucurbitae Drosophila suzukii
• Hydrellia griseola Fly Rhacochlaena japonica
• Muscina STABULANS no -nominated (Megaselia Spiracularis), noimi blades (Clogmia Albipunctata), Kirijuri Gambo (Tipula Aino), Crokin Bae (PH).
• Hymenoptera (Hymenoptera) pests include, for example, Pristomyrmex ponnes, wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, and Formica fusca japonica. , wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Arge mali. (Ochetellus glaber) etc.
• Orthoptera pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, and Oxya japonica. (Homorocoryphus jezoensis), and Enma cricket (Teleogryllus emma).
• thrips pests include red-throated thrips (Selenothrips rubrocinctus), rice thrips (Stenchaetothrips biformis), rice thrips (Haplothrips aculeatus), Ponticulothrips diospyrosi, yellow thrips (Thrips flavus), Lower Thrips (Anaphothrips obscurus) , Cusukuda thrips (Liothrips floridensis), Gladiolus thrips (Thrips simplex), Black thrips (Thrips nigropilosus), Croton thrips (Heliothrips haemorrhoidalis), Swamp thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips Abdomin) alis), Thrips Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips
• Examples of insect pests in the order of Acari include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Demodex canis.
• Ticks such as Tetranychus viennensis, Tetranychus kanzawai, Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, Latrodectus hasseltii), Formosan cactus Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis , Sarcoptes scabiei), black-legged tick (Haemaphysalis longicornis), black-legged tick (Ixodes scapularis), spinach spider mite (Tyrophagus similis), white spider mite (Cheyletus eruditus), orange spider mite (Panonychus citri
• termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., and Reticulitermes flaviceps amamianus. , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Formosan termite Odontotermes formosanus) , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
• Examples of pests of the order Cockroaches include the black cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Japanese cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the Japanese cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach. (Periplaneta americana) etc.
• Examples of the order Flea include the human flea (Pulex irritans), the cat flea (Ctenocephalides felis), and the chicken flea (Ceratophyllus gallinae).
• nematodes examples include the strawberry nematode (Nothotylenchus acris), the rice nematode (Aphelenchoides besseyi), the northern nematode (Pratylenchus penetrans), the northern nematode (Meloidogyne hapla), the sweet potato nematode (Meloidogyne incognita), and the potato cyst nematode (Globodera).
• rostochiensis Javan cat nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern coffeae (Pratylenchus coffeae), barley coffeae (Pratylenchus neglectus), and citrus nematode (Tylenchus semipenetrans).
• molluscs examples include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. can be mentioned.
• the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against other pests such as tomato absolutea (Tuta absoluta).
• animal parasitic ticks that are targeted for control include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and Haemaphysalis campanulata.
• Tani mites derMANYSSUS gallinee, trisasus sylviarum, and southern minitisus bursa ), such as Eutrombicula wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, and Neotrombicula autumnalis.
• chiggers such as dog mites (Cheyletiella yasguri), rabbit mites (Cheyletiella parasitivorax), and cat claw mites (Cheyletiella blakei); Demodex mites, such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabii, and Notoedres cati; and Demodex mites, Demodex canis. etc.
• fleas to be controlled include, for example, ectoparasitic wingless insects belonging to the order Siphonaptera, more specifically fleas belonging to the family Pulicidae and the family Ceratephyllus.
• fleas belonging to the human flea family include dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Echidnophaga gallinacea), Cheops rat flea (Xenopsylla cheopis), and blind rat flea (Ctenocephalides felis).
• Leptopsylla segnis European mouse flea (Nosopsyllus fasciatus), and mountain mouse flea (Monopsyllus anisus).
• ectoparasites to be controlled include, for example, cow lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), haematophagous dipterans such as bullfly (Tabanus trigonus), dogfish (Culicoides schultzei), and snail flycatcher (Simulium ornatum). Examples include pests.
• endoparasites include lungworms, tuberculous worms, tuberculous worms, gastric parasites, roundworms, and nematodes such as threadworms; tapeworms, such as tapeworms, tapeworms, tapeworms, and tapeworms; trematodes, such as Schistosoma japonicus, and liver fluke; and coccidia, malaria parasites, enteric sarcosporidians, and toxoplasma. , and protozoa such as Cryptosporidium.
• the agricultural and horticultural insecticide containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention can be used against the above-mentioned pests that cause damage to paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc. Because it has a remarkable control effect on pests, it is necessary to prevent pests from occurring in seedling facilities, paddy fields, fields, fruit trees, vegetables, and other crops before the outbreak of pests or when the outbreak is confirmed.
• the desired effects of the agricultural and horticultural insecticide of the present invention can be achieved by treating it with cultivation carriers such as seeds of flowers, paddy water, stems and leaves, or soil.
• the compound of the present invention can be absorbed through the roots through or without the soil by treating the soil for raising seedlings of crops, flowers, etc., the soil for planting holes during transplanting, the roots of plants, irrigation water, cultivation water for hydroponic cultivation, etc.
• a preferred form of use is application that takes advantage of the so-called permeability and migration properties.
• Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited; (adzuki beans, fava beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbages, Tomatoes, spinach, broccoli, lettuce, onions, green onions (morning onions, spring onions), green peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, lotus root, burdock) , garlic, rakkyo, etc.), processed crops (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), cucurbits (pumpkins, cucumbers, watermelons, melons, etc
• plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, and setoxydim. Also included are plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
• HPPD inhibitors such as isoxaflutole
• ALS inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthase inhibitors such as glyphosate
• glutamine synthetase inhibitors such as glufosinate
• setoxydim setoxydim.
• plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors,
• plants that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, and rice, which are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
• rapeseed, wheat, sunflower, and rice which are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
• Clearfield registered trademark
• STS soybean sulfonylurea-based ALS-inhibiting herbicides
• SR corn is an example of a plant that has been made resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
• acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
• plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990).
• mutant acetyl-CoA carboxylase that is resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol.
• Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing them into plants or by introducing mutations that confer resistance into plant acetyl-CoA carboxylase inhibitors.Furthermore, chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) is introduced into plant cells to introduce site-specific amino acids into plant acetyl-CoA carboxylase genes, ALS genes, etc. By introducing substitution mutations, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc., and the agricultural and horticultural insecticide of the present invention can also be used for these plants. .
• insecticidal proteins derived from Bacillus cereus and Bacillus popilliae such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis; Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, rufin, saporin, and bryo
• RIPs ribosome inactivating proteins
• toxins expressed in such genetically modified plants include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, VIP1, VIP2, VIP3, or VIP3A, etc.
• Hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins are also included. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology.
• Cry1Ab which has a partially deleted amino acid sequence, is known as a partially deleted toxin.
• a modified toxin has one or more amino acids substituted for the naturally occurring toxin.
• the toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes.
• the agricultural and horticultural insecticide of the present invention can be used in combination with or systematized with those techniques.
• the agricultural and horticultural insecticide of the present invention can be used as it is, diluted with water, etc., or suspended in an amount effective for controlling the pests or nematodes.
• pests and nematodes that occur in fruit trees, cereals, vegetables, etc.
• Culper Seed treatments such as full layer soil mixing, row application, bed soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. It can also be used by absorption.
• the agricultural and horticultural insecticide of the present invention may be used as it is, or diluted with water or the like, or in a suspended form, in an amount effective for controlling pests, at locations where the pests are expected to occur.
• the agricultural and horticultural insecticide of the present invention may be used as it is, or diluted with water or the like, or in a suspended form, in an amount effective for controlling pests, at locations where the pests are expected to occur.
• it in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on house building materials, smoke, bait, etc.
• Seed treatment methods include, for example, diluting a liquid or solid preparation or immersing the seeds in an undiluted liquid state to infiltrate the seeds, mixing a solid or liquid preparation with the seeds, or coating the seeds with powder. Examples include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or polymer and coating the seeds, and a method of spraying near the seeds at the same time as planting.
• seed used for the seed treatment refers to plants in the early stage of cultivation used for plant propagation, such as seeds, bulbs, tubers, seed potatoes, shoots, bulbs, scales, or cuttings for cultivation. Examples include plants for vegetative propagation.
• soil or “cultivation carrier” for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, especially a support for growing roots, and the material is not particularly limited. However, any material that plants can grow on may be used, such as soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, and high-quality materials. It may also be a molecular substance, rock wool, glass wool, wood chips, bark, etc.
• liquid preparations such as emulsions and flowables, or solid preparations such as wettable powders or granule wettable powders, are diluted with water as appropriate.
• a method of spraying a method of spraying a powder, a method of smoking, etc.
• Methods for applying to soil include, for example, applying liquid preparations to the base of plants or seedling beds without diluting them with water, or applying granules to the base of plants or seedling beds.
• Methods of spraying on seedbeds, etc. methods of spraying powders, wettable powders, hydrated granules, granules, etc.
• the dosage form may vary depending on the time of application, such as application at sowing, application during greening, application at transplanting, etc. It can be applied in a mold. It can also be applied by mixing with the soil, such as by mixing the soil with a powder, a granular wettable powder, a granule, etc., for example, mixing with bed soil, mixing with soil covering, or mixing with the entire soil. You may simply apply the soil and various preparations in alternating layers.
• solid preparations such as jumbo preparations, pack preparations, granules, and wettable powders
• liquid preparations such as flowables and emulsions
• a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer.
• a chemical solution such as an emulsion or a flowable at the source of water flowing into the rice field, such as a water outlet or an irrigation system, it can be applied in a labor-saving manner as water is supplied.
• seeds or cultivation carriers close to the plants can be treated during the seeding to seedling-raising period.
• treatment to the roots of plants under cultivation is suitable.
• Spraying treatment using granules or irrigation treatment can be carried out in liquid form with a chemical that is diluted with water or not diluted. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow the seeds.
• Treatments during the sowing and seedling-raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as irrigation treatment with liquid chemicals or spraying treatment with granules on seedling beds.
• the agricultural and horticultural insecticide of the present invention is generally formulated into a form convenient for use according to conventional methods for agricultural chemical formulations. That is, the compound represented by the general formula (1) of the present invention or its salts can be dissolved, separated, or suspended by blending them in an appropriate inert carrier or with an adjuvant as necessary in an appropriate ratio. It can be used by clouding, mixing, impregnating, adsorbing or adhering it into an appropriate dosage form, such as suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack, etc. Good.
• composition of the present invention may contain, in addition to the active ingredient, additive components commonly used in agricultural chemical preparations or animal parasite control agents, if necessary.
• additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , anti-caking agents, disintegrants, anti-decomposition agents and the like.
• Other additives such as preservatives and plant pieces may be used as necessary.
• solid carriers examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as vegetable powders (e.g. sawdust, coconut shell, corncob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.
• natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomace
• liquid carriers examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
• alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF, etc.
• ethers normal paraffin, naphthene, isoparaffin, kerosene, aliphatic hydrocarbons such as mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc.
• Halogenated hydrocarbons esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, etc.
• lactones such as ⁇ -butyrolactone
• amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, etc.
• examples include nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.
• surfactants used as dispersants and wetting agents include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Alkylene-a
• binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6,000 to 20,000.
• (meth)acrylic acid copolymers half esters of polyhydric alcohol polymers and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffins, terpenes, polyamide resins, polyacrylates, polyoxy Examples include ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
• thickeners examples include water-soluble polymers such as xanthan gum, guar gum, diurtan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, polysaccharides, high-purity bentonite, and fumed silica.
• Inorganic fine powders such as silica, white carbon, etc.
• coloring agent examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
• antifreeze agents examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
• adjuvants to prevent caking and promote disintegration include starch, alginic acid, polysaccharides such as mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer Examples include polymers.
• decomposition inhibitors include drying agents such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It will be done.
• preservatives examples include potassium sorbate and 1,2-benzothiazolin-3-one.
• other aids such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may be added. Agents can also be used.
• the blending ratio of the active ingredient compound can be adjusted as necessary, and it may be used by appropriately selecting from the range of 0.01 to 90 parts by weight based on 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
• the appropriate amount is 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide).
• the amount of the agricultural and horticultural insecticide of the present invention to be used depends on various factors, such as the purpose, target pests, crop growth conditions, pest outbreak trends, weather, environmental conditions, dosage form, application method, application location, and application time. Although it varies, it may be selected as appropriate from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares of the active ingredient compound depending on the purpose.
• the agricultural and horticultural insecticide of the present invention can be used in conjunction with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, etc. for the purpose of expanding the pests and diseases to be controlled, the appropriate period for control, or reducing the dosage. It can be used in combination with biological pesticides, etc., and it can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the usage situation.
• XMC 3,5-xylyl methylcarbamate
• BPMC fenobucarb
• BPMC fenobucarb
• DCIP
• Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, and acibenzolar-S-methyl. ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, uniconazole,
• herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, icafolin-methyl, aclonifen, azafenidin, acifluorfen, aziprotrine, azimus azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone ( amicarbazone), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridi
• biopesticides include, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV). ), insecticides or nematicides such as Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.
• a microbial pesticide used as a fungicide for Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
• a similar effect can be expected by mixing with the microbial pesticides used, and biological pesticides used as herbicides such as Xanthomonas campestris.
• biopesticides such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E,Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icocen-10-one, 14-methyl-1 - It is also possible to use it in combination with a pheromone agent such as octadecene.
• a pheromone agent such as octadecene.
• Reference example 1 Tert-butyl 5-((4-fluorophenyl)carbamothioyl)-4-hydroxy-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1 (6H)-Carboxylate production reference example 1-1 Production of tertiary-butyl 4-hydroxy-6-oxo-2-(6-(trifluoromethyl)pyridin-3-yl)-2,3-dihydropyridazine-1(6H)-carboxylate
• Formulation example 1 Compound of the present invention: 10 parts Xylene: 70 parts N-methylpyrrolidone: 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate: 10 parts The above ingredients are uniformly mixed and dissolved to form an emulsion.
• Formulation example 2 Compound of the present invention: 3 parts Clay powder: 82 parts Diatomaceous earth powder: 15 parts The above ingredients are uniformly mixed and pulverized to obtain a powder.
• Formulation example 3 Compound of the present invention: 5 parts Mixed powder of bentonite and clay: 90 parts Calcium ligninsulfonate: 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, kneaded, granulated, and dried to obtain granules.
• Formulation example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to prepare a wettable powder.
• Test example 1 Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released on Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with eggs were treated with the compound represented by the general formula (1) of the present invention. The samples were immersed for about 30 seconds in a drug solution containing a drug as an active ingredient diluted to 50 ppm or 500 ppm, air-dried, and then left in a constant temperature room at 25°C. The number of surviving insects was investigated after 6 days of immersion in the chemical solution, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive races.
• Test example 2 Insecticidal test against Laodelphax striatellus
• the compound represented by the general formula (1) of the present invention or its salts is dispersed in water, diluted to 50 ppm or 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical solution. After soaking for 30 seconds and air drying, place in a glass test tube, inoculate each with 10 instars of the 3rd instar brown planthopper, then plug with cotton plugs. 8 days after inoculation, examine the number of live and dead insects, and calculate the corrected mortality rate using the formula below. It was calculated and judged according to the judgment criteria of Test Example 1.
• Test example 3 Insecticidal test against occidental thrips (Frankliniella occidentalis) Female adult occidental thrips were inoculated onto kidney bean leaf pieces, and after laying eggs for one day, the female adults were removed. After three days, the hatched larvae on the leaf pieces were counted, and then a chemical solution containing the compounds listed in Tables 1 to 4 as active ingredients diluted to 50 ppm or 500 ppm was sprayed. Four days after the treatment, the number of surviving larvae of this species was investigated, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the criteria of Test Example 1. Two in a row.
• the compound of the present invention or its salt has excellent effects as an insecticide.

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• 2023
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