WO2017061497A1 - Composé hétérocyclique condensé ou sels de celui-ci, insecticide à visée agricole et horticole le contenant, et son procédé d'utilisation - Google Patents

Composé hétérocyclique condensé ou sels de celui-ci, insecticide à visée agricole et horticole le contenant, et son procédé d'utilisation Download PDF

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WO2017061497A1
WO2017061497A1 PCT/JP2016/079677 JP2016079677W WO2017061497A1 WO 2017061497 A1 WO2017061497 A1 WO 2017061497A1 JP 2016079677 W JP2016079677 W JP 2016079677W WO 2017061497 A1 WO2017061497 A1 WO 2017061497A1
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group
halo
alkyl group
alkyl
alkoxy
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PCT/JP2016/079677
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Japanese (ja)
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彰浩 宮坂
樹 米村
諏訪　明之
隼平 藤江
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日本農薬株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to a condensed heterocyclic compound or a salt thereof, an agricultural and horticultural insecticide containing the compound or a salt thereof as an active ingredient, and a method of using the insecticide.
  • the condensed heterocyclic compound represented by the general formula (1) or a salt thereof has a broad insecticidal spectrum and excellent against various pests in the agricultural and horticultural fields.
  • the present invention has been completed by finding that it has a control effect, has high mammal safety, and has moderate degradation in the environment, so that the burden on the environment is light.
  • R 1 is (a1) (C 1 -C 6 ) alkyl group; (a2) (C 3 -C 6 ) cycloalkyl group; (a3) (C 2 -C 6 ) alkenyl group; or (a4) (C 2 -C 6 ) alkynyl group; and.
  • R 2 is (b1) a halo (C 1 -C 6 ) alkyl group; (b2) a halo (C 1 -C 6 ) alkoxy group; (b3) a halo (C 1 -C 6 ) alkylthio group; (b4) a halo (C 1 -C 6 ) alkylsulfinyl group; or (b5) a halo (C 1 -C 6 ) alkylsulfonyl group;
  • a 1 , A 2 , A 3 and A 4 may be the same or different and each represents a nitrogen atom or CR 3 , B 1 and B 2 represent a nitrogen atom or CR 4 , and B 3 and B 4 represent a nitrogen atom, N—R 5 , C—R 6 , an oxygen atom, or a sulfur atom, and G 1 , G 2, and G 3 represent a nitrogen atom or a carbon atom.
  • R 3 is (c1) a hydrogen atom; (c2) a halogen atom; (c3) a cyano group; (c4) a nitro group; (c5) (C 1 -C 6 ) alkyl group; (c6) (C 3 -C 6 ) cycloalkyl group; (c7) (C 1 -C 6 ) alkoxy group; (c8) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl groups; (c9) a halo (C 1 -C 6 ) alkyl group; (c10) a halo (C 1 -C 6 ) alkoxy group; (c11) (C 1 -C 6 ) alkylthio group; (c12) (C 1 -C 6 ) alkylsulfinyl group; (c13) (C 1 -C 6 ) alkylsulfonyl group; (c14) a halo (C 1 -C 6
  • R 5 is (d1) a hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group; or (d4) halo (C 1 -C 6 ) alkyl group; R 4 , R 6 and R 7 may be the same or different and are (e1) hydrogen atom; (e2) halogen atom; (e3) cyano group; (e4) nitro group; (e5) (C 1 -C 6 ) An alkyl group; or (e6) (C 1 -C 6 ) alkoxy group; m represents 0, 1, or 2.
  • R 2 represents (b1) a halo (C 1 -C 6 ) alkyl group; A 1 , A 3 and A 4 represent C—H; The condensed heterocyclic compound or a salt thereof according to any one of [1] to [3], wherein A 2 represents C—R 3 (wherein R 3 represents a cyclopropyl group;), [6] An agricultural and horticultural insecticide comprising the compound or salt thereof according to any one of [1] to [5] as an active ingredient, [7] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with an effective amount of the agricultural and horticultural insecticide according to [6], [8] A mammalian ectoparasite control agent comprising an effective amount of the compound or salt thereof according to any one of [1] to [5] as an active ingredient, [9] General formula (1) ⁇ Wherein R 1 represents (a1) (C 1 -C 6 ) alkyl group; A 1 , A 3 and A 4 represent
  • R 3 represents (c1) hydrogen atom; (c2) halogen atom; (c3) cyano group; (c4) nitro group; (c5) (C 1 -C 6 ) alkyl group; (c6) (C 3 -C 6 ) Cycloalkyl group, (c7) (C 1 -C 6 ) alkoxy group; (c8) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, (c9) halo (C 1 -C 6 ) Alkyl group; (c10) halo (C 1 -C 6 ) alkoxy group; (c11) (C 1 -C 6 ) alkylthio group; (c12) (C 1 -C 6 ) alkylsulfinyl group; (c13) (C 1 -C 6) alkylsulfonyl group; (c14) halo (C 1 -C 6) alkylthio group; (c15) halo (C
  • C ( R 10) NOR 11 groups (wherein R 10 and R 11 may be the same or different and are a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 2 -C 6 ) alkenyl group, (C 2 -C 6 ) alkynyl) Group, (C 3 -C 6 ) cycloalkyl group, (C 3 -C 6 ) Cycloalkyl (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkoxy (C 1 -C 6) alkyl group, a phenyl group, or a phenyl (indicating the C 1 -C 6) alkyl group);.
  • R 10 and R 11 may be the same or different and are a hydrogen atom, (C 1 -C 6 )
  • (c 20) a phenyl group; (c21) may be the same or different, (a) A halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) a halo (C 1 -C 6 ) alkyl group, (g ) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group , (M) a halo (C 1 -C 6
  • R 5 is (d1) a hydrogen atom; (d2) a (C 1 -C 6 ) alkyl group; (d3) a cyclo (C 3 -C 6 ) alkyl (C 1 -C 6 ) alkyl group; or (d4) a halo (C 1 -C 6 ) alkyl group; R 4 , R 6 and R 7 may be the same or different and are (e1) hydrogen atom; (e2) halogen atom; (e3) cyano group; (e4) nitro group; (e5) (C 1 -C 6 ) An alkyl group; or (e6) (C 1 -C 6 ) alkoxy group; m represents 0, 1, or 2.
  • a 1 , A 2 , A 3 and A 4 represent CR 3 (wherein R 3 is the same as defined above), and B 1 and B 2 represent a nitrogen atom or CR 4 (wherein R 4 is the same as above), B 3 and B 4 are a nitrogen atom, or N—R 5 (wherein R 5 is the same as above), and G 1 , G 2 and G 3 each represent a carbon atom, the imidazopyridine compound or a salt thereof according to [9], [11] R 1 represents a (a1) (C 1 -C 6 ) alkyl group; R 2 represents a (b1) halo (C 1 -C 6 ) alkyl group; and A 1 , A 2 , A 3 and A 4 represent C—R 3 , B 1 and B 2 represent a nitrogen atom, or C—R 4 (wherein R 4 represents a hydrogen atom), and B 3 and B 4 represents a nitrogen atom or N—R 5 (
  • R 3 is (c1) hydrogen atom; (c2) halogen atom; (c3) cyano group; (c5) (C 1 -C 6 ) alkyl group; (c7) (C 1 -C 6 ) alkoxy group; (c9) halo (C 1 -C 6 ) alkyl group; (c10) halo (C 1 -C 6 ) alkoxy group; (c11) (C 1 -C 6 ) alkylthio group; (c12) (C 1 -C 6 ) Alkylsulfinyl group; (c13) (C 1 -C 6 ) an alkylsulfonyl group; (c14) a halo (C 1 -C 6 ) alkylthio group; (c15) a halo (C 1 -C 6 ) alkylsulfinyl group; (c16) a halo (C 1 -C 6 ) alkylsulfonyl group; (
  • R 8 (R 9) N group (wherein, R 8 and R 9, R 8 and described in [1] The same as R 9 )), and R 7 represents (e1) a hydrogen atom; or an imidazopyridine compound or a salt thereof according to [9] or [10], [12]
  • R 1 represents (a1) (C 1 -C 6 ) alkyl group
  • R 2 represents (b1) halo (C 1 -C 6 ) alkyl group
  • a 1 , A 2 , A 3 and A 4 represent CR 3 , B 1 and B 2 represent a nitrogen atom or CR 4 , B 3 and B 4 represent a nitrogen atom or N—R 5 , G 1 , G 2 and G 3 represent carbon atoms
  • R 3 represents (c9) halo (C 1 -C 6 ) alkyl group
  • R 5 represents (d 2) (C 1 -C 6 ) alkyl group
  • R 4 and R 7 are (e1) a hydrogen atom, or an imidazopyr
  • the fused heterocyclic compound of the present invention or a salt thereof not only has an excellent effect as an agricultural and horticultural insecticide, but is also suitable for non-human pets such as dogs and cats, or pests parasitic on the outside of livestock such as cattle and sheep. Also effective.
  • the compound of the present invention has a broad insecticidal spectrum, and has excellent control effects against a wide range of pests such as pests in the field of paddy rice such as planthoppers, horticultural pests such as butterflies and stink bugs (aphids, etc.). Have.
  • the compound of the present invention has both safety for mammals such as human bodies and livestock, and environmental safety, which are important factors when developing as an agricultural chemical.
  • acute toxicity is light, there is no serious concern in tests such as long-term toxicity and carcinogenicity, there is little effect on environmental organisms such as daphnia, and useful insects such as bees, and it is moderately appropriate in the environment such as water and soil. It is a drug that decomposes and has a low environmental impact such as accumulation.
  • halo means “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, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, 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, A linear 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. .
  • the “(C 3 -C 6 ) cycloalkyl group” means a cyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., and “(C 1- Examples of the “C 6 ) alkoxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, and a tertiary group.
  • Pentyloxy group Pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl group
  • examples of the “(C 2 -C 6 ) alkynyloxy group” include linear or branched carbon such as propynyloxy group, butynyloxy group, pentynyloxy group, hexynyl
  • Examples of the “(C 1 -C 6 ) alkylthio group” include a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, and a normal pentylthio group.
  • alkyl sulfinyl group and the "(C 1 -C 6) alkylsulfonyl group", for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl Group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1 1 to 6 carbon atoms having 1 to 6 linear or branched chain such as -ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal
  • Halo (C 1 -C 6 ) alkyl group “halo (C 2 -C 6 ) alkenyl group”, “halo (C 2 -C 6 ) alkynyl group”, “halo (C 3 -C 6 )”, respectively “Cycloalkyl group”, “halo (C 3 -C 6 ) cycloalkyloxy group”, “halo (C 1 -C 6 ) alkoxy group”, “halo (C 2 -C 6 ) alkenyloxy group”, “halo ( “C 2 -C 6 ) alkynyloxy group”, “halo (C 1 -C 6 ) alkylthio group”, “halo (C 1 -C 6 ) alkylsulfinyl group”, “halo (C 1 -C 6 ) alkylsulfonyl group” ”,“ Halo (C 2 -C 6 ) alkenylthio ”,“ halo (C 2 -C 6 ) al
  • Expressions such as “(C 1 -C 6 )”, “(C 2 -C 6 )”, “(C 3 -C 6 )” indicate the range of the number of carbon atoms of various substituents. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group”, it is linear or branched. It indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.
  • Heterocyclic group and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms. Group heterocyclic groups and the corresponding heterocyclic rings.
  • heterocyclic group examples include monocyclic rings such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl, and the like. And a formula aromatic heterocyclic group.
  • Examples of the salt of the condensed heterocyclic compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and salt.
  • examples include organic acid salts such as acid salts, methanesulfonic acid salts, benzenesulfonic acid salts, paratoluenesulfonic acid salts, and salts with inorganic or organic bases such as sodium ions, potassium ions, calcium ions, and trimethylammonium salts. it can.
  • the condensed heterocyclic compound represented by the general formula (1) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more optical isomers and dia Stereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio.
  • the compound represented by the general formula (1) and salts thereof of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. Includes all geometric isomers and mixtures containing them in any proportion.
  • a 1 , A 2 , A 3 and A 4 are preferably CR 3
  • B 1 and B 2 are nitrogen atoms or C-R 4 is preferably
  • B 3 and B 4 are nitrogen atoms, or N-R 5 by weight
  • G 1, G 2 and G 3 preferably carbon atoms.
  • R 1 is (a1) (C 1 -C 6 ) alkyl group; and R 2 is (b1) halo (C 1 -C 6 ) alkyl group; and A 1 , A 2 , A 3 and A 4 are C—R 3 , B 1 is a nitrogen atom, B 2 is C—R 4 , B 3 is N—R 5 , B 4 is A nitrogen atom, G 1 , G 2 and G 3 are carbon atoms, R 3 is (c1) a hydrogen atom; (c2) a halogen atom; (c6) (C 3 -C 6 ) cycloalkyl group; c9) a halo (C 1 -C 6 ) alkyl group; (c10) a halo (C 1 -C 6 ) alkoxy group; (c14) a halo (C 1 -C 6 ) alkylthio group; (c15) a halo (C 1 -C 6) alkylsulfin
  • R 1 is an (a1) (C 1 -C 6 ) alkyl group
  • R 2 is a (b1) halo (C 1 -C 6 ) alkyl group
  • a 1 , A 3 And A 4 is C—H
  • a 2 is C—R 3
  • B 1 is a nitrogen atom
  • B 2 is C—R 4
  • B 3 is N—R 5
  • B 4 is a nitrogen atom
  • G 1 , G 2 and G 3 are carbon atoms
  • R 3 is a (c6) (C 3 -C 6 ) cycloalkyl group
  • R 5 is , (D2) (C 1 -C 6 ) alkyl group
  • R 4 and R 7 are (e1) hydrogen atoms
  • R 1 , A 3 And A 4 is C—H
  • a 2 is C—R 3
  • B 1 is a nitrogen atom
  • B 2 is C—R 4
  • B 3 is N—R 5
  • B 4 is a nitrogen atom
  • R 1 is (a1) (C 1 -C 6 ) alkyl; and R 2 is (b1) halo (C 1 -C 6 ) alkyl; and A 1 , A 3 And A 4 is C—H, A 2 is C—R 3 , B 1 is a nitrogen atom, B 2 is C—R 4 , and B 3 is N—R 5 And B 4 is a nitrogen atom, G 1 , G 2 and G 3 are carbon atoms, R 3 is a cyclopropyl group; and R 5 is (d2) (C 1 -C 6 And R 4 and R 7 are (e1) a hydrogen atom;
  • the fused heterocyclic compound or salts thereof of the present invention can be produced, for example, by the following production method, but the present invention is not limited to these.
  • step [a] By reacting the carboxylic acid ester represented by the general formula (3) and the compound represented by the general formula (4) in the presence of a base and an inert solvent, the general formula (2)
  • the carboxylic acid amide compound represented by these can be manufactured.
  • This reaction can be carried out according to a method described in the literature (Org. Synth. 78, 23; Coll. Vol. 10, 423, JACS (1999), 121 (18), 4369-4378). it can.
  • carboxylic acid when using carboxylic acid, it can manufacture by the method described in the international publication 2013/018928 pamphlet, the international publication 2013/180193 pamphlet, or the international publication 2015/133603 pamphlet.
  • Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, and potassium hydrogen carbonate. Hydrogenation, carbonates such as calcium carbonate, magnesium carbonate, acetates such as lithium acetate, sodium acetate, potassium acetate, alkoxides such as sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium tertiary butoxide, etc. Examples thereof include metal hydrides such as sodium and potassium hydride, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, diethyl ether, tetrahydrofuran (THF), dioxane, and the like.
  • Linear or cyclic ethers such as benzene, toluene, xylene and other aromatic hydrocarbons, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene , Nitriles such as acetonitrile, esters such as ethyl acetate (AcOEt), polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone You can cite these Active solvents may be used singly or as mixtures of two or more.
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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 the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Further, the next step may proceed without isolation / purification. In some cases, the dehydration condensation reaction for the next step proceeds in this production step, and the next step can be omitted.
  • the compound represented by the general formula (1-1) can be produced by reacting the compound represented by the general formula (2) with an acid in the presence of an inert solvent.
  • an inert solvent e.g., diethyl azodicarboxylate (DEAD) or dimethoxyethyl azodicarboxylate (DMEAD) and triphenylphosphine (Ph 3 P) described in the literature (Bull. Chem. Soc. Jpn., 1967, 40, 935) are used. Can also be manufactured.
  • Examples of the acid 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.
  • examples thereof include sulfonic acid (PTS) such as sulfonic acid, phosphoric acid and the like.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether (MTBE), dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethyl
  • inert solvents such as amides such as formamide, dimethylacetamide, N-methylpyrrolidone, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone
  • inert solvents are Germany or in combination of two or more can be used.
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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 the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the compound represented by the general formula (1a) is produced by reacting the compound represented by the general formula (1-1) with an oxidizing agent in an inert solvent.
  • an oxidizing agent used in this reaction include peroxides such as hydrogen peroxide solution, perbenzoic acid, and m-chloroperbenzoic acid (m-CPBA).
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonization such as benzene, toluene, and xylene.
  • chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane
  • aromatic carbonization such as benzene, toluene, and xylene.
  • Hydrogens, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
  • Organic solvents N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone, water and the like, and these inert solvents can be used alone or A mixture of more than one species can be used.
  • the reaction temperature in this reaction may be appropriately selected within 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, and the like, and is not constant but may be appropriately selected within 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 the target product in which m is 1 or 2 is produced by recrystallization or column chromatography as necessary. can do.
  • the compound represented by the general formula (1-c2) is obtained by reacting the compound (1-c1) produced by the production method 1 with a method described in literature, for example, Metal catalyzed Cross-coupling Reactions and More, Wiley-VCH (2014 / 03/31), or Cross-coupling Reactions: A Practical Guide (Topics in current Chemistry), Cross-coupling reaction according to the method described in Springer Reed (2010/12/01), or Substitution Reaction 20 9/6) according to the method described in 9/6).
  • a method described in literature for example, Metal catalyzed Cross-coupling Reactions and More, Wiley-VCH (2014 / 03/31), or Cross-coupling Reactions: A Practical Guide (Topics in current Chemistry), Cross-coupling reaction according to the method described in Springer Reed (2010/12/01), or Substitution Reaction 20 9/6) according to the method described in 9/6).
  • Production method of steps [a] and [b] The method [a] and [b] described in the production method 1 include the carboxylic acid ester represented by the general formula (3b) and the compound represented by the general formula (4). ], The compound represented by the general formula (1-1b) can be produced.
  • the compound represented by the general formula (1-1) can be produced according to the method described in the production method for the intermediate (3) below from the compound represented by the general formula (1-1b). Then, according to the method [c] described in the production method 1, the compound represented by the general formula (1a) in which m is 1 or 2 can be produced.
  • the compound represented by the general formula (10) is obtained by using the compound represented by the general formula (4) as a starting material.
  • the compound represented by the general formula (11) is obtained by using the compound represented by the general formula (10) as a reaction raw material. L. 46 (30), 5081-5084, 2005.
  • the compound represented by the general formula (12) can be produced by reacting the compound represented by the general formula (11) with a halogenating agent in an inert solvent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include chain or cyclic ethers such as diethyl ether, aromatic hydrocarbons such as benzene, toluene, and xylene, and chloride.
  • halogenated hydrocarbons such as methylene, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, organic acids such as formic acid and acetic acid, and solvents such as water.
  • inert solvents can be used alone or in admixture of two or more.
  • the halogenating agent that can be used in this reaction include N-chlorosuccinimide, sulfuryl chloride, bromine, N-bromosuccinimide, and diiodohydantoin (DIH).
  • this reaction is an equimolar reaction, an equimolar amount of the halogenating agent may be used with respect to the compound (11), but an excess of the halogenating agent may be used.
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within 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 the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Further, the next step may proceed without isolation / purification.
  • the compound represented by the general formula (1-1b) can be produced by using the compound represented by the general formula (12) as a reaction raw material according to the method described in the production method for the intermediate (3) below. Then, according to the method [c] described in the production method 1, the compound represented by the general formula (1a) in which m is 1 or 2 can be produced.
  • the compound of the general formula (3) which is the compound of the present invention can be produced by the following method.
  • the carboxylic acid ester compound represented by the general formula (3-2) the amino compound represented by the general formula (3-3) and the halopyruvic acid ester (5) are described in International Publication No. 2009/115651. It can be made to react according to the method.
  • the halocarboxylic acid ester compound represented by the general formula (3-1) can be produced by reacting the carboxylic acid ester compound represented by the general formula (3-2) with a halogenating agent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol
  • chains such as diethyl ether, tetrahydrofuran, and dioxane are used.
  • cyclic ethers aromatic hydrocarbons such as benzene, toluene, xylene, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone
  • polar solvents such as water and acetic acid.
  • halogenating agent used in the reaction examples include fluorine, chlorine, bromine, iodine halogen molecules, halogenated succinimides such as NCS and NBS, DIH (1,3-diiodo-5,5-dimethylhydantoin), etc. And halogenated hydantoins, thionyl chloride and the like.
  • the reaction temperature in this reaction may be appropriately selected within 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, and the like, and is not constant but may be appropriately selected within 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. If necessary, the halocarboxylic acid ester compound (3-1) is produced by recrystallization, column chromatography or the like. can do.
  • the carboxylic acid ester compound represented by the general formula (3) is obtained by cross-linking a halocarboxylic acid ester compound represented by the general formula (3-1) and a compound represented by the general formula (6) under an inert solvent. It can be produced by ring reaction.
  • palladium compounds such as zero-valent or divalent palladium metals and salts (including complexes) can be used, and they may be supported on activated carbon or the like.
  • Preferable products include palladium (0) / carbon, palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tris (dibenzylideneacetone) dipalladium (0), tetrakis (Triphenylphosphine) palladium (0) and the like can be mentioned.
  • This reaction can also be performed by adding a ligand.
  • the ligand include triphenylphosphine (PPh 3 ), methyldiphenylphosphine (Ph 2 PCH 3 ), trifurylphosphine (P (2-furyl) 3 ), tri (o-tolyl) phosphine (P (O-tol) 3 ), tri (cyclohexyl) phosphine (PCy 3 ), dicyclohexylphenylphosphine (PhPCy 2 ), tri (t-butyl) phosphine (Pt-Bu 3 ), 2,2′-bis (diphenylphosphino) -1, 1'-binaphthyl (BINAP), diphenylphosphinoferrocene (DPPF), 1,1'-bis (di-t-butylphosphino) ferrocene (Dt-BPF), N, N-dimethyl-1- [2- ( Diphen
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, potassium t Alkali metal alkoxides such as butoxide, sodium methoxide, sodium ethoxide, tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, pyridine, dimethyl Nitrogen-containing aromatic compounds such as aminopyridine can be mentioned, and the amount used is usually in the range of 1 to 10 moles compared to the halocarboxylic acid ester compound represented by the general formula (3-1). Is done.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate
  • acetates such as sodium acetate and potassium acetate
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Chain hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • chain ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran and 2-methyltetrahydrofuran (2-MeTHF), acetic acid
  • inert solvents such as esters such as ethyl, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone Can these Inert solvents may be used singly or as mixtures of two or more.
  • the compound represented by general formula (6) and the halocarboxylic acid ester compound represented by general formula (3-1) may be used in equimolar amounts. It can also be used in excess.
  • the reaction temperature can be from 0 ° C. in the boiling range of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in 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 the target product (3) can be produced by purification by recrystallization, column chromatography or the like, if necessary. .
  • the compound represented by the general formula (4a) of the compound of the present invention can be produced by the following method.
  • palladium compounds such as zero-valent or divalent palladium metals and salts (including complexes) can be used, and the palladium compounds may be supported on activated carbon or the like.
  • Preferred examples include palladium (0) / carbon, palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tetrakis (triphenylphosphine) palladium (0), and the like. I can do things.
  • This reaction can also be performed by adding a ligand.
  • the ligand include triphenylphosphine (PPh 3 ), methyldiphenylphosphine (Ph 2 PCH 3 ), trifurylphosphine (P (2-furyl) 3 ), tri (o-tolyl) phosphine (P (o-tol) 3 ), tri (cyclohexyl) phosphine (PCy 3 ), dicyclohexylphenylphosphine (PhPCy 2 ), tri (t-butyl) phosphine (Pt-Bu 3 ), 2,2′-bis (diphenylphosphino) -1, 1′-binaphthyl (BINAP), diphenylphosphinoferrocene (DPPF), 1,1′-bis (di-t-butylphosphino) ferrocene (Dt-BPF), N, N-dimethyl-1- [2 -(
  • Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, cesium carbonate, and the like.
  • Examples thereof include organic bases such as picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine.
  • the amount of the base used may be appropriately selected from the range of 1 mol to 5.0 mol with respect to the compound represented by the general formula (4a-3).
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. .
  • the aminopyridazine compound represented by the general formula (4a-2) can be produced by reacting the pyridazine compound represented by the general formula (4a-3) with the amino compound (R 5 NH 2 ).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
  • the inert solvent include amides such as acetamide, ketones such as acetone and methyl ethyl ketone, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone. Can be used by mixing more than one species
  • a base may be used.
  • the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; sodium acetate, potassium acetate, etc.
  • Acetates alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide, tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene
  • Nitrogen-containing aromatic compounds such as pyridine, dimethylaminopyridine and the like, and the amount used thereof is usually in the range of 1 to 10 mol per mol of the compound represented by the general formula (4a-3). Used in.
  • the reaction temperature in this reaction may be appropriately selected within 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, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • the amino compound (R 5 NH 2 ) can be appropriately selected within a range of 1 to 5 moles relative to the pyridazine compound represented by the general formula (4a-3).
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • a halopyridazine compound represented by the general formula (4a-1) can be produced by reacting the aminopyridazine compound represented by the general formula (4a-2) with a halogenating agent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol
  • chains such as diethyl ether, tetrahydrofuran, and dioxane Or cyclic ethers
  • aromatic hydrocarbons such as benzene, toluene, xylene
  • esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolide
  • Nonpolar, water, acetic acid and other polar solvents can be mentioned, and these inert solvents can be used alone or in admixture of two or more.
  • halogenating agent used in the reaction examples include halogen molecules such as chlorine, bromine and iodine, halogenated succinimides such as NCS and NBS, DBH (1,3-dibromo-5,5-dimethylhydantoin), DIH and the like. Halogenated hydantoins, thionyl chloride and the like can be mentioned.
  • the reaction temperature in this reaction may be appropriately selected within the range of ⁇ 30 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within 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 the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the aminopyridazine compound (4a) can be produced by reacting the halopyridazine compound represented by the general formula (4a-1) with ammonia in the presence of a copper catalyst and a solvent.
  • the inert solvent used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction.
  • alcohols such as methanol, ethanol, propanol, butanol and 2-propanol
  • aromatics such as benzene, toluene and xylene.
  • Inert solvents such as amides, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.
  • copper catalyst used in this reaction copper oxide, copper bromide, copper chloride and the like can be used.
  • the amount used can be appropriately selected within the range of 1 to 5 moles compared to the halopyridazine compound represented by the general formula (4a-1).
  • the reaction temperature in this reaction may be appropriately selected within 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, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • Ammonia can be appropriately selected in the range of 1 to 5 moles relative to the halopyridazine compound represented by the general formula (4a-1).
  • an autoclave can be used.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Me represents a methyl group
  • Et represents an ethyl group
  • i-Pr is an isopropyl group
  • c-Pr is a cyclopropyl group
  • t-Bu is a tertiary butyl group
  • c-Hex is a cyclohexyl group
  • Ac represents an acetyl group
  • Ph represents a phenyl group.
  • Physical properties indicate melting point (° C.) or 1 H-NMR, and NMR data are shown in Tables 27 and 36.
  • the agricultural and horticultural insecticide containing the condensed heterocyclic compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry and horticultural plants that harm paddy rice, fruit trees, vegetables, other crops, and florets. Suitable for controlling pests such as stored pests, sanitary pests, nematodes and the like.
  • Examples of the pests or nematodes include the following. Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empti (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayoto (Pseudaletia separata), Iga (Tinea translucens), Bactra furfuryla, Parnara guttata, Ira inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (Helicoverpa armigera) Phararodonta man
  • Hemiptera pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito) , St
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice beetle (Oulema oryzae), rice beetle (Donacia provosti), rice weevil (Lissorhoptruss (Epilachna varivestis), common bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), potato beetle (Aulacophora f
  • Culex pipiens pallens red flies fly (Pegomya hyoscyami), red spider fly (Liriomyza huidobrensis), house fly (Musca domestica), rice flies Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), giant butterflies (Clogmia albipunctata), mushroom moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platura), Onion fly (Delia antiqua) RRen ), Ceratitis capitata, Bradysia agrestis, sugar beetle fly (P
  • Hymenoptera Pristomyrmex ⁇ ponnes
  • Arbatidae Moneorumium pharaohnis
  • Pheidole noda Athalia rosae
  • Cristoforma Kuriphilus
  • Hornets black bee (Athalia infumata infumata), horned bee (Arge g pagana), Japanese bee (Athalia ⁇ japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen ali) (Ochetellus glaber) and the like.
  • insects of the order Diptera Hortocoryphus lineosus
  • Kera Gryllotalpa sp.
  • Coago Oxya hyla intricata
  • Cobainago Oxya yezoensis
  • Tosama locust Locusta migrago
  • Oneya Homorocoryphus jezoensis
  • emma cricket Teogryllus emma
  • Thrips examples of thrips of the order Thrips (Selenothrips rubrocinctus), thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Helothripes Leeuwenia pasanii), Shiritakuthamis (Litotetothrips pasaniae), Citrus srips (Scirtothrips citri), Hempothrips chinensis, Soybean thrips (Mycterothrips glycines), Da Thrips setosus, Thripsrtsaw Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and the like.
  • mite moths (Leptotrombidium akamushi), Ashinowa spider mite (Tetranychus ludeni), American dock ticks (Dermacentor variabilis), Ichinami spider mite (Tetranychus truncatus), house dust mite (Ornithonyssus bacoti), mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus) and other ticks (Cheyletus acc malaccensis), stag beetle tick (Tyrophagus putrescent moth) Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (
  • Amite termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes termm ants) , Glyptotermes , Nakaly termites (Glyptotermes nakajimai), Nitobe termites (Pericapritermes nitobei), Yamato termites (Reticulitermes speratus) and the like.
  • cockroach Periplaneta fuliginosa
  • German cockroach Blattella germanica
  • Great cockroach Blatta orientalis
  • Greater cockroach Periplaneta brunnea
  • Greater cockroach Blattella lituriplanet (Periplaneta americana) and the like.
  • fleas examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).
  • Nematodes for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-footed nematode (Pratylenchus penetrans), red-knot nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne rostochiensis), Javaloid nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), and pterolenchus nematode (Pratylenchus neglectus)
  • mollusks examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta Is mentioned.
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • animal parasite ticks Boophilus microplus
  • black tick ticks Raicephalus sanguineus
  • yellow tick ticks Haemaphysalis longicornis
  • yellow ticks Haemaphysalis flava
  • tsurigane tick ticks Haemaphysata tick
  • Tick Haemaphysalis concinna
  • tick Haemaphysalis japonica
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis ias
  • tick Ixodes ovatus
  • tick desmite Ticks Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae
  • avian mite Ornithonyssus sylviarum
  • fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • ectoparasites to be controlled include, for example, cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle lice (Linognathus vituli), pig lice (Haematopinus ⁇ suius ⁇ pubis), And lice like head lice (Pediculus capitis), and lice like dog lice (Trichodectes canis), blood-sucking dipteries such as Tabibus trigonus, Culicoides schultzei, and Simulium ornatum Examples include pests.
  • endoparasites include nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms, flukes such as Schistosoma japonicum, and liver fluke, and coccidium, malaria parasites, intestinal granulocysts, toxoplasma And protozoa such as Cryptosporidium.
  • nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms,
  • the agricultural and horticultural insecticide containing the fused heterocyclic compound represented by the general formula (1) or a salt thereof of the present invention as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers. It has a remarkable control effect on the pests that it gives, so that it matches the time when the occurrence of the pests is predicted, before the occurrence of the pests or when the occurrence is confirmed, nursery facilities, paddy fields, fields, fruit trees, vegetables, etc.
  • the desired effects of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds such as crops, seeds such as flower buds, paddy field water, stalks and leaves or soil and other cultivation carriers.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomato, spinach, broccoli, lettuce, onion, green onion (satsuki, parrot), green pepper, eggplant, strawberry, pepper, ladle, leek, etc., root vegetables (carrot, potato, sweet potato, sweet potato, daiko, kabu, lotus root, gobo) , Garlic, raccoon, etc.), crops for processing (crab, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as
  • Plants to which tolerance to an acetyl-CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance into a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • a nucleic acid introduced with a base substitution mutation is introduced into a plant cell.
  • site-specific amino acid substitution mutations into the chill CoA carboxylase gene, ALS gene, etc.
  • plants resistant to acetyl CoA carboxylase inhibitors, ALS inhibitors, etc. can be created.
  • the agricultural and horticultural insecticides of the invention can be used.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
  • ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab,
  • Bosome inactivating protein RIP
  • Steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878, WO 03. / 052073 and the like.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination or systematized with these techniques.
  • the insecticide for agricultural and horticultural use according to the present invention is used as it is to control various pests, or appropriately diluted with water or the like, or suspended in an amount effective for controlling the pests or nematodes.
  • pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc.
  • it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted.
  • they can also be used as application to house building materials, smoke, bait and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at the initial stage of cultivation used for the propagation of plants, for example, for seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings. Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a spraying method for crop foliage stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate.
  • Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application during sowing, greening period, application during transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • the plant source of the plant being cultivated In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling.
  • treatment on the plant source of the plant being cultivated is suitable.
  • a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred.
  • a granule is treated in a planting hole at the time of planting or mixed with a cultivation carrier in the vicinity of the transplantation site.
  • the agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations. That is, the condensed heterocyclic compound represented by the general formula (1) of the present invention or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required.
  • additive components include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.
  • the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier 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.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols 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, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as 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 esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants 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 is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 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 depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be suitably selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg depending on the purpose.
  • Agricultural and horticultural insecticides of the present invention are pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, for the purpose of expanding the appropriate period of control or reducing the dose. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the usage situation.
  • Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, eclomeole, echlomez Edifenphos, etaconazole, ethaboxam, e
  • herbicides for example, 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, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), Amibu Amibuzin, amiprophos-methyl,
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) Virus preparations, Monocrosporium ⁇ ⁇ phymatophagum, Steinernema ⁇ carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
  • microbial pesticide to be used by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies 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-icosen-10-one, 14-methyl-1 - May also be used in combination with pheromone agents such as octadecene It is a function.
  • pheromone agents such as octadecene It is a function.
  • Reference example 1 Process for the preparation of N- (3-methylamino-6-pentafluoroethylpyridazin-4-yl) -3-ethylthio-6-trifluoromethylimidazo [1,2-a] pyridine-2-carboxylic acid amide 4-Amino-3-methylamino-6-pentafluoroethylpyridazine (229 mg, 0.943 mmol) was dissolved in dehydrated THF (10 mL), NaH (60% in oil, 41.5 mg, 1.04 mmol) was added, Stir at room temperature for 10 minutes.
  • Example 2 2- (3-Ethylsulfinyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-c] pyridazine ( Compound No. 1-128) and 2- (3-Ethylsulfonyl-6-trifluoromethylimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4 , 5-c] pyridazine (Compound No.
  • Example 4 2- (3-Ethylsulfonyl-7-chloroimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (Compound No. 2-129) Production method 2- (3-Ethylthio-7-chloroimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (37.3 mg , 0.0906 mmol) was dissolved in AcOEt (0.9 mL), m-CPBA (ca. 70%, 55.9 mg, 0.226 mmol) was added, and the mixture was stirred at room temperature for 12 hours.
  • m-CPBA ca. 70%, 55.9 mg, 0.226 mmol
  • Reference example 2 Process for producing 3-ethylthio-N- (2-hydroxy-5- (trifluoromethylthio) phenyl) -7-trifluoromethylimidazo [1,2-a] pyridine-2-carboxamide 3-ethylthio-7-trifluoromethylimidazo [1,2-a] pyridine-2-carboxylic acid (151 mg, 0.520 mmol) was added to DMF (0.040 mL), CHCl3 (6.0 mL), oxalyl chloride (132 mg). 1.04 mmol) and stirred at room temperature for 30 minutes.
  • Example 5 Process for producing 2- (3-ethylthio-7-trifluoromethylimidazo [1,2-a] pyridin-2-yl) -5-trifluoromethylthiobenzo [d] oxazole (Compound No. 6-16) To 3-ethylthio-N- (2-hydroxy-5- (trifluoromethylthio) phenyl) -7-trifluoromethylimidazo [1,2-a] pyridine-2-carboxamide (87.4 mg, 0.182 mmol), Triphenylphosphine (52.5 mg, 0.200 mmol), dimethoxyethyl azodicarboxylate (DMEAD) (46.8 mg, 0.200 mmol), and THF (2.0 mL) were added, and the mixture was stirred under reflux conditions for 2 hours.
  • DMEAD dimethoxyethyl azodicarboxylate
  • THF 2.0 mL
  • Example 6 2- (3-Ethylsulfonyl-7-trifluoromethylimidazo [1,2-a] pyridin-2-yl) -5-trifluoromethylthiobenzo [d] oxazole (Compound No. 6-18) and 2- (3 Process for producing 2-ethylsulfonyl-7-trifluoromethylimidazo [1,2-a] pyridin-2-yl) -5-trifluoromethylsulfinylbenzo [d] oxazole (Compound No.
  • Example 7 2- (3-Ethylthio-6-iodoimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (Compound No. 2 -13) Production method 2- (3-Chloro-6-iodoimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo prepared by the method of Reference Example 1 and Example 1 NaSEt (35.3 mg, 0.420 mmol) and DMA (5 mL) were added to [4,5-b] pyridine (67.0 mg, 0.140 mmol), and the mixture was stirred at 150 ° C. for 1 hour.
  • Example 10 3- (Ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) imidazo [1,2-a] pyridine-7- Method for producing carboxaldehyde 2- (3-Ethylsulfonyl-7-vinylimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (67.
  • NMO N-methylmorpholine N-oxide
  • THF 4 mL
  • pH 7 buffer aqueous solution 2 mL
  • OsO 4 0.039 m in t-BuOH, 0.6 mL, 0.0234 mmol
  • NaIO 4 38.0 mg, 0.178 mmol
  • the reaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated.
  • Example 12 N- (3- (ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) imidazo [1,2-a] pyridine -7-yl) acetamide (Compound No. 2-162) 2- (3-Ethylsulfonyl-7-bromoimidazo [1,2-a] pyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4 prepared according to the method of Example 4 above.
  • Example 15 8-Bromo-3- (ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridin-2-yl) imidazo [1,2-a] Pyridine-7-amine (Compound No. 8-3), and 6,8-dibromo-3- (ethylsulfonyl) -2- (3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5- b] Pyridin-2-yl) imidazo [1,2-a] pyridin-7-amine (Compound No.
  • reaction mixture was diluted with ethyl acetate, quenched with a hypo aqueous solution, the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated.
  • Reference Example 6 Process for producing 2- (7-bromoimidazo [1,2-a] pyridin-2-yl) -6-trifluoromethylimidazo [4,5-b] pyridine 2- (2-Bromoacetyl) -6-trifluoromethylimidazo [4,5-b] pyridine (200 mg) and 2-amino-4-bromopyridine (124 mg) prepared by the method of Reference Example 5 were mixed with ethanol. Dissolved in (3 mL). In addition, the mixture was heated to reflux for 1 hour.
  • 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 is uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to obtain a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
  • Control value test against peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated.
  • the condensed heterocyclic compound represented by the general formula (1) of the present invention or a salt thereof is dispersed in water and diluted to 500 ppm of a chemical solution.
  • the chemical solution is sprayed on the stems and leaves of a potted Chinese cabbage and air-dried.
  • the number of parasites of the peach aphid parasitizing each Chinese cabbage on the 6th day after drug spraying was calculated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
  • Ta Number of parasites before spraying in the treated zone
  • Ca Number of parasites before spraying in the untreated zone
  • C Number of parasites after spraying in the untreated zone
  • the compounds of the present invention 1-7, 1-9, 1-10, 1-12, 1-121, 1-123, 1-124, 1-126, 1-127, 1-128, 1-129 , 1-130, 1-132, 1-298, 1-300, 1-352, 1-354, 2-1, 2-3, 2-7, 2-9, 2-10, 2-11, 2 -12, 2-13, 2-15, 2-16, 2-18, 2-124, 2-126, 2-127, 2-129, 2-132, 2-141, 2-144, 2-162 2-168, 2-235, 2-237, 2-238, 2-240, 2-243, 2-244, 2-246, 2-249, 2-250, 2-252, 2-255, 2 -258, 2-261, 2-264, 2-267, 2-270, 2-273, 2-276, 2-279, 2-282 2-285, 2-390, 3-1, 3-3, 3-4, 3-6, 4-1, 4-3, 4-7, 4-9, 4-10, 4-12, 4- 13, 4-15, 4-18, 4-19, 4-21, 4-24, 5-1,
  • Test Example 2 Insecticidal test against Japanese brown planthopper (Laodelphax striatella)
  • the condensed heterocyclic compound represented by the general formula (1) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and then rice seedlings (variety: Nipponbare) Was soaked for 30 seconds, air-dried, put into a glass test tube, inoculated with 10 each of the three Japanese beetles, and then plugged, and after 8 days of inoculation, the number of live and dead insects was investigated. And the determination was made according to the determination criteria of Test Example 1.
  • the compounds of the present invention 1-7, 1-9, 1-10, 1-12, 1-121, 1-123, 1-124, 1-126, 1-127, 1-128, 1-129 , 1-130, 1-132, 1-298, 1-300, 1-352, 1-354, 2-1, 2-3, 2-7, 2-9, 2-10, 2-11, 2 -12, 2-13, 2-15, 2-16, 2-18, 2-124, 2-126, 2-127, 2-129, 2-132, 2-141, 2-144, 2-162 2-168, 2-235, 2-237, 2-238, 2-240, 2-243, 2-244, 2-246, 2-249, 2-250, 2-252, 2-255, 2 -258, 2-261, 2-264, 2-267, 2-270, 2-273, 2-276, 2-279, 2-282 2-285, 2-390, 3-1, 3-3, 3-4, 3-6, 4-1, 4-3, 4-7, 4-9, 4-10, 4-12, 4- 13, 4-15, 4-18, 4-19, 4-21, 4-24, 5-1,
  • Test Example 3 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and two days after the release, cypress seedlings with spawning eggs are condensed into a complex of the general formula (1) of the present invention.
  • the drug containing a ring compound as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C.
  • Six days after immersion in the chemical solution the number of hatching insects was investigated, and the death rate was calculated according to the following formula. 1 ward, 10 heads, 3 systems.
  • the compounds of the present invention 1-7, 1-9, 1-10, 1-12, 1-121, 1-123, 1-124, 1-126, 1-127, 1-128, 1-129 , 1-130, 1-132, 1-298, 1-300, 1-352, 1-354, 2-1, 2-3, 2-7, 2-9, 2-10, 2-11, 2 -12, 2-13, 2-15, 2-16, 2-18, 2-124, 2-126, 2-127, 2-129, 2-132, 2-141, 2-144, 2-162 2-168, 2-235, 2-237, 2-238, 2-240, 2-243, 2-244, 2-246, 2-249, 2-250, 2-252, 2-255, 2 -258, 2-261, 2-264, 2-267, 2-270, 2-273, 2-276, 2-279, 2-282 2-285, 2-390, 3-1, 3-3, 3-4, 3-6, 4-1, 4-3, 4-7, 4-9, 4-10, 4-12, 4- 13, 4-15, 4-18, 4-19, 4-21, 4-24, 5-1,
  • the compounds according to the present invention have an excellent control effect against a wide range of agricultural and horticultural pests and are useful.

Abstract

Les dommages occasionnés par les insectes nuisibles et autres restant significatifs dans la production des cultures agricoles ou horticoles, la présente invention concerne un composé hétérocyclique condensé ou des sels de celui-ci, ledit composé étant un nouveau composé insecticide à visée agricole et horticole pour lutter contre la présence, etc., d'insectes nuisibles résistant aux produits existants, représenté par la formule générale (1) (dans la formule, R1 représente (a1) un groupe alkyle (C1-C6), et R2 représente (b1) un groupe haloalkyle (C1-C6) ; A1, A3, et A4 représentent un groupe CH ; A2 représente un groupe C-CF3 ; B1 et B2 représentent un atome d'azote ou un groupe CH ; B3 représente N-Me ; B4 représente un atome d'azote ; et G1, G2, et G3 représentent un atome de carbone ; R3 représente (c7) un groupe haloalkyle (C1-C6), R5 représente (d2) un groupe alkyle (C1-C6), et R4 et R7 représentent (e1) un atome d'hydrogène ; et m représente 0, 1 ou 2). Un insecticide contenant le composé selon l'invention, et son procédé d'utilisation sont en outre décrits.
PCT/JP2016/079677 2015-10-06 2016-10-05 Composé hétérocyclique condensé ou sels de celui-ci, insecticide à visée agricole et horticole le contenant, et son procédé d'utilisation WO2017061497A1 (fr)

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