WO2018105632A1 - Composé de quinoléine ayant un groupe carbamate, sel de celui-ci, insecticide pour une utilisation agricole et horticole contenant ledit composé, et utilisation dudit insecticide - Google Patents

Composé de quinoléine ayant un groupe carbamate, sel de celui-ci, insecticide pour une utilisation agricole et horticole contenant ledit composé, et utilisation dudit insecticide Download PDF

Info

Publication number
WO2018105632A1
WO2018105632A1 PCT/JP2017/043733 JP2017043733W WO2018105632A1 WO 2018105632 A1 WO2018105632 A1 WO 2018105632A1 JP 2017043733 W JP2017043733 W JP 2017043733W WO 2018105632 A1 WO2018105632 A1 WO 2018105632A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
halo
beetle
agricultural
salt
Prior art date
Application number
PCT/JP2017/043733
Other languages
English (en)
Japanese (ja)
Inventor
直登 清水
樹 米村
諏訪　明之
綾介 田中
隼平 藤江
Original Assignee
日本農薬株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本農薬株式会社 filed Critical 日本農薬株式会社
Publication of WO2018105632A1 publication Critical patent/WO2018105632A1/fr

Links

Classifications

    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to an agricultural and horticultural insecticide containing a quinoline compound having a carbamate group or a salt thereof as an active ingredient, and a method of using the same.
  • Patent Documents 1 to 8 Such documents do not disclose any quinoline compounds having a carbamate group.
  • the present inventors have found that the quinoline compound having a carbamate group represented by the general formula (1) or a salt thereof has an excellent control effect against agricultural and horticultural pests. At the same time, the present inventors have found that it is environmentally degradable and has little influence on environmental organisms such as bees.
  • R 1 is (a1) (C 1 -C 6 ) alkyl group; (a2) halo (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4 ) (C 2 -C 6) alkynyl group; and; (a5) (C 3 -C 6) cycloalkyl group; or (a6) (C 3 -C 6 ) cycloalkyl (C 1 -C 6) alkyl group .
  • R 2 represents (b1) a hydrogen atom; (b2) a (C 1 -C 6 ) alkyl group; (b3) a halo (C 1 -C 6 ) alkyl group; (b4) (C 1 -C 6 ) alkoxy (C 1 -C 6) alkyl group; (b5) cyano (C 1 -C 6) alkyl group; (b6) (C 3 -C 6) cycloalkyl group; or (b7) (C 3 -C 6 ) cycloalkyl ( C 1 -C 6 ) alkyl group; R 3 is (c1) halogen atom; (c2) cyano group; (c3) nitro group; (c4) (C 1 -C 6 ) alkyl group; (c5) (C 1 -C 6 ) alkoxy group; ) (C 2 -C 6 ) alkenyloxy group; (c7) (C 2 -C 6 ) alkynyloxy group; (c8)
  • A represents an oxygen atom or N—R 4 (wherein R 4 represents (e1) a hydrogen atom; or (e2) (C 1 -C 6 ) an alkyl group); and A 1 and A 2 may be the same or different and each represents CH or a nitrogen atom, m represents 0, 1, or 2, and n represents 0, 1, or 2.
  • a quinoline compound or a salt thereof [2] The quinoline compound or a salt thereof according to [1], wherein A is an oxygen atom, [3] The quinoline compound or a salt thereof according to [1], wherein A is N-Me, [4] An agricultural and horticultural insecticide comprising the quinoline compound or a salt thereof according to any one of [1] to [3] as an active ingredient, [5] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with an effective amount of the quinoline compound or salt thereof according to any one of [1] to [3], [6] An ectoparasite control agent for animals comprising the quinoline compound or a salt thereof according to any one of [1] to [3] as an active ingredient.
  • the quinoline compound having a carbamate group of the present invention or a salt thereof not only has an excellent effect as an agricultural and horticultural insecticide, but also a pest parasitic on domestic animals such as dogs and cats other than humans and cattle and sheep. It also has an excellent effect.
  • 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 2 -C 6 ) alkenyl group” refers to a linear or branched alkenyl group having 2 to 6 carbon atoms such as a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, and the like.
  • the “(C 2 -C 6 ) alkynyl group” refers to a linear or branched alkynyl group having 2 to 6 carbon atoms such as propynyl group, butynyl group, pentynyl group, hexynyl group and the like.
  • the "(C 3 -C 6) cycloalkyl group” include cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an alkyl group having a carbon number of 3 to 6 ring such as a cyclohexyl group, "(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
  • Linear or branched C1-C6 alcohols such as oxy groups
  • a “(C 2 -C 6 ) alkenyloxy group” is, for example, a straight chain or branched chain carbon atom number 2 to 2 such as propenyloxy group, butenyloxy group, pentenyloxy group, hexenyloxy group, etc.
  • 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 , Normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethyl Linear or branched alkylsulfonyl having 1 to 6 carbon atoms such as propylsulfonyl group, 1-methylbutylsulfonyl group
  • halo (C 1 -C 6 ) alkyl group halo (C 2 -C 6 ) alkenyl group
  • halo (C 2 -C 6 ) alkynyl group halo (C 2 -C 6 ) alkynyl group
  • halo (C 3 -C 6) cycloalkyl group "halo (C 1 -C 6) alkoxy group”, “halo (C 2 -C 6) alkenyloxy group”, “halo (C 2 -C 6 ) alkynyloxy group ",” halo (C 3 -C 6) cycloalkyl group "," halo (C 1 -C 6) alkylthio group ",” halo (C 1 -C 6) alkylsulfinyl group ",” halo (C 1 -C 6 ) alkylsulfonyl ”,“ halo (C 2 -C 6 ) alkenylthio ”,“ halo (C 2 -C 6 ) alkenylthio ”,“ halo (C 2 -C 6 ) alkenylsulfinyl ”,“ halo (C 2 -C 6 ) alkenyl sulfonyl group ",” hal
  • 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 shown for a group to which the above substituent is linked. For example, in the case of a “(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group”, a linear or branched chain 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.
  • Examples of the salt of the quinoline compound having a carbamate group represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate and maleate.
  • Illustrate organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium salt be able to.
  • the quinoline compound having a carbamate group represented by the general formula (1) and salts thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers may be present. And diastereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. Further, the quinoline compound having a carbamate group represented by the general formula (1) of the present invention and salts thereof may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. However, the present invention encompasses all geometric isomers and mixtures containing them in any proportion.
  • R 1 is (a1) (C 1 -C 6 ) alkyl group; and R 2 is (B1) hydrogen atom; (b2) (C 1 -C 6 ) alkyl group; (b3) halo (C 1 -C 6 ) alkyl group; (b4) (C 1 -C 6 ) alkoxy (C 1 -C) 6) alkyl group; or (b5) cyano (C 1 -C 6) alkyl group; a, R 3 is, (c8) halo (C 1 -C 6) alkyl group; (c15) halo (C 1 -C 6 ) an alkylthio group; or (d17) a halo (C 1 -C 6 ) alkylsulfonyl group.
  • A is an oxygen atom or N—R 4 (wherein R 4 is (e1) a hydrogen atom; or (e2) (C 1 -C 6 ) an alkyl group); and A 1 and A 2 may be the same or different and are CH or a nitrogen atom, m is 2, and n is 1.
  • the quinoline compound having a carbamate group or a salt thereof of the present invention can be produced by, for example, the following production method, but the present invention is not limited thereto.
  • R 1 , R 2 , R 3 , A, A 1 , A 2 , and n are the same as described above, and X represents a leaving group such as a halogen atom.
  • the quinoline compound represented by the general formula (1-2) is a haloquinoline compound represented by the general formula (1-5) produced by the method described in International Publication No. 2016/091731 pamphlet. And a carbamate compound according to the method described in J. A. C. S., 2002, 124 (21), 6043-6048, in the presence of a metal catalyst and a base, in an inert solvent, a cross-coupling reaction Can be manufactured.
  • the quinoline compound represented by the general formula (1-1) comprises a quinoline compound represented by the general formula (1-2) and R 2 X represented by the general formula (2). It can be produced by reacting in the presence of an inert solvent and a base.
  • Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and alkali metals such as sodium hydride and potassium hydride.
  • examples include hydrides, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and tertiary butoxy potassium, and alkyl lithiums such as methyl lithium and normal butyl lithium.
  • the amount used is usually in the range of 1.0 to 10 moles compared to the haloquinoline compound represented by the general formula (1-5) or the quinoline compound represented by the general formula (1-2). Is done.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • examples thereof include alcohols such as methanol, ethanol and isopropanol; diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran and the like.
  • examples of the inert solvent include linear or cyclic ethers; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and nitriles such as acetonitrile. Or a mixture of two or more.
  • R 1 , R 2 , R 3 , A, A 1 , A 2 , and n are the same as described above, and X represents a leaving group such as a halogen atom.
  • step [A] The quinoline compound represented by the general formula (1-4) can be produced by the same method as the method of step A of production step 1.
  • the quinoline compound represented by the general formula (1-3) can be produced according to the method described in ORGANIC FUNCTIONAL GROUP PREPARATIONS III 2th edition ACADEMI PRESS, INC.
  • 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 quinoline compound represented by the general formula (1-2) is ORGANIC FUNCTIONAL GROUP PREPARATIONS III 2th edition ACADEMI PRESS, INC. It can be produced according to the method described in 1. After completion of the reaction, 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.
  • step [B] The quinoline compound represented by the general formula (1-1) can be produced by the same method as the method of step B of production step 1.
  • Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr represents a normal propyl group
  • i-Pr represents an isopropyl group.
  • the physical properties indicate melting point (° C.) or 1 H-NMR. 1 H-NMR data are shown in Table 13.
  • the agricultural and horticultural insecticide containing a quinoline compound having a carbamate group represented by the general formula (1) of the present invention or a salt thereof as an active ingredient is a variety of agricultural and forestry that harms paddy rice, fruit trees, vegetables, other crops and flowers. It is suitable for pest control such as horticulture, stored grain pests, hygiene pests or nematodes, and pests that parasitize inside and outside of animals.
  • 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), rush saint moth (Bactra furfurana), Ichinomosei (Parnara guttata), Inaitei inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (
  • 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-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito
  • 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 weevil (Donacia provosti), rice weevil (Lissorhoptrus oryzophilus), Weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), weevil weevil (Involvulus cupreus), weevil (Aulacophora femoralis), pea weevil (Bruchus pisorum) Epilachna viginti
  • 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 Monomelium pharaonis
  • 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), Shiritaku Thrips pasaniae, Citrus Srips citri, Hypothrips 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 , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (Pericapritermes nitobei), Yamato termite (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 rat 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 such as head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), buffalo (Tabanus trigonus), green hawks (Culicoides schultzei), and blood-sucking dipterans such as 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 insecticides containing the quinoline compound having a carbamate group represented by the general formula (1) of the present invention or a salt thereof as an active ingredient are paddy field crops, field crops, fruit trees, vegetables, other crops, flower buds, etc. It has a remarkable control effect against the pests that cause damage to the pests, so that it matches the time when the occurrence of the pests is predicted, before the occurrence of the pests or at the time when the occurrence is confirmed, paddy field, field, fruit tree,
  • the desired effects of the agricultural and horticultural insecticide of the present invention can be achieved by treating the seeds such as vegetables, other crops, flower buds, paddy 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, Tomatoes, spinach, broccoli, lettuce, onions, green onions (satsuki, parsley), peppers, eggplants, strawberries, peppers, ladle, leek, etc.
  • 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, pe
  • 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 or 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-like substances, 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 is 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 quinoline compound having a carbamate group represented by the general formula (1) or a salt thereof of the present invention is blended in an appropriate inert carrier or, if necessary, with an auxiliary agent in an appropriate ratio.
  • Dissolve, separate, suspend, mix, impregnate, adsorb or adhere to appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable powders, granules, powders, tablets, packs, etc. It can be used by formulating.
  • 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, phospholipids (eg, cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid and styrene Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, Fins, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipids eg, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • 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 Gin (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.
  • Example 1 Process for producing 6-ethoxycarbonylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (Compound No. 3-6) 6-Amino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (30 mg, 0.07 mmol) prepared in the previous step was added to THF (tetrahydrofuran) (2.0 mL).
  • THF tetrahydrofuran
  • Example 2 Process for producing 7-ethoxycarbonylamino-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (Compound No. 4-6) 7-Bromo-3- (ethylsulfonyl) -2- (5- (trifluoromethylthio) benzoxazol-2-yl) quinoline (20 mg, 0.04 mmol) prepared by the method described in WO2016 / 091731 was dissolved in toluene.
  • FIG. Preparation of 7-Ethoxycarbonylamino-3-ethylsulfonyl-2- (6-pentafluoroethyl-3-methyl-3H-imidazo [4,5-C] pyridazin-2-yl) quinoline (Compound No.
  • 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 form 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.
  • Test Example 1 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 quinoline compound having a carbamate group 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 potted Chinese cabbage and air-dried.
  • 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 area
  • Ca Number of parasites before spraying in the untreated area
  • C Number of parasites after spraying in the untreated area
  • the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A. , A activity was shown.
  • the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A. Showed the activity of A.
  • Test Example 3 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and carpate seedlings with spawning eggs two days after the release are expressed by the carbamate group represented by the general formula (1) of the present invention.
  • a quinoline compound having a quinoline compound as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and left in a thermostatic chamber at 25 ° C.
  • Six days after immersion in the chemical solution the number of hatching insects was investigated, the death rate was calculated by the following formula, and the determination was made according to the criteria of Test Example 2. 1 ward, 10 heads, 3 systems.
  • the compounds of the present invention 1-6, 2-1, 2-6, 2-7, 2-10, 2-11, 2-16, 2-21, 3-1, 3-6, 3-7 3-16, 4-6, 4-7, 4-26, 4-27, 4-46, 6-6, 6-7, 6-26, 6-27, 7-1, 7-2, and 7-3 showed the activity of A.
  • the compound according to the present invention has an excellent control effect against a wide range of agricultural and horticultural pests and is useful.

Abstract

La présente invention aborde le problème du développement et de la fourniture d'un nouveau insecticide à usage agricole et horticole pour des raisons telles qu'il y a encore d'importants dégâts sur la production des cultures agricoles et horticoles par des parasites et des organismes nuisibles résistants aux produits chimiques classiques ont apparus. La présente invention concerne un composé de quinoléine ayant un groupe carbamate représenté par la formule générale (1) (dans laquelle R1 représente un groupe alkyle ; R2 représente un atome d'hydrogène ou un groupe alkyle ; R3 représente un groupe haloalkyle ; A1 représente un atome d'oxygène ou un groupe N-Me ; A1 représente un atome d'azote ; A2 représente CH ; m représente 2 ; et n représente 1) ou un sel de celui-ci ; un insecticide à usage agricole et horticole, qui contient le composé ou un sel de celui-ci en tant que principe actif ; et l'utilisation de l'insecticide à des fins agricoles et horticoles.
PCT/JP2017/043733 2016-12-07 2017-12-06 Composé de quinoléine ayant un groupe carbamate, sel de celui-ci, insecticide pour une utilisation agricole et horticole contenant ledit composé, et utilisation dudit insecticide WO2018105632A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2016-237324 2016-12-07
JP2016237324 2016-12-07
JP2017-077088 2017-04-07
JP2017077088 2017-04-07

Publications (1)

Publication Number Publication Date
WO2018105632A1 true WO2018105632A1 (fr) 2018-06-14

Family

ID=62491141

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/043733 WO2018105632A1 (fr) 2016-12-07 2017-12-06 Composé de quinoléine ayant un groupe carbamate, sel de celui-ci, insecticide pour une utilisation agricole et horticole contenant ledit composé, et utilisation dudit insecticide

Country Status (1)

Country Link
WO (1) WO2018105632A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
WO2020173861A1 (fr) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
CN112824402A (zh) * 2019-11-21 2021-05-21 浙江省化工研究院有限公司 一类苯并咪唑类衍生物、其制备方法及应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014005263A (ja) * 2011-08-04 2014-01-16 Sumitomo Chemical Co Ltd 縮合複素環化合物及びその有害生物防除用途
WO2015002211A1 (fr) * 2013-07-01 2015-01-08 住友化学株式会社 Composé hétérocyclique condensé et son utilisation pour lutter contre les ravageurs
WO2016091731A1 (fr) * 2014-12-11 2016-06-16 Syngenta Participations Ag Dérivés tétracycliques à action pesticide comportant des substituants contenant du soufre
WO2016121997A1 (fr) * 2015-01-29 2016-08-04 日本農薬株式会社 Composé hétérocyclique fusionné contenant un groupe cycloalkylpyridyle ou un sel de celui-ci, et insecticide agricole ou horticole contenant ledit composé et procédé d'utilisation associé

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014005263A (ja) * 2011-08-04 2014-01-16 Sumitomo Chemical Co Ltd 縮合複素環化合物及びその有害生物防除用途
WO2015002211A1 (fr) * 2013-07-01 2015-01-08 住友化学株式会社 Composé hétérocyclique condensé et son utilisation pour lutter contre les ravageurs
WO2016091731A1 (fr) * 2014-12-11 2016-06-16 Syngenta Participations Ag Dérivés tétracycliques à action pesticide comportant des substituants contenant du soufre
WO2016121997A1 (fr) * 2015-01-29 2016-08-04 日本農薬株式会社 Composé hétérocyclique fusionné contenant un groupe cycloalkylpyridyle ou un sel de celui-ci, et insecticide agricole ou horticole contenant ledit composé et procédé d'utilisation associé

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10640518B2 (en) 2016-03-10 2020-05-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10759815B2 (en) 2016-03-10 2020-09-01 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
WO2020173861A1 (fr) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
CN112824402A (zh) * 2019-11-21 2021-05-21 浙江省化工研究院有限公司 一类苯并咪唑类衍生物、其制备方法及应用
CN112824402B (zh) * 2019-11-21 2023-02-28 浙江省化工研究院有限公司 一类苯并咪唑类衍生物、其制备方法及应用

Similar Documents

Publication Publication Date Title
JP6581284B2 (ja) ベンゾオキサゾール化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
JP6577051B2 (ja) ３ｈ‐ピロロピリジン化合物若しくはそのｎ‐オキサイド、又はそれらの塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
JP6388671B2 (ja) シクロアルキルピリジル基を有する縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
JP6263166B2 (ja) 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2016104746A1 (fr) Composé hétérocyclique à groupe cycloalkyle condensé, sel de celui-ci, insecticide agricole et horticole le contenant, et son procédé d&#39;utilisation
WO2017061497A1 (fr) Composé hétérocyclique condensé ou sels de celui-ci, insecticide à visée agricole et horticole le contenant, et son procédé d&#39;utilisation
WO2016039441A1 (fr) Composé imidazopyridazine ou ses sels et insecticide agricole et horticole contenant ledit composé et son procédé d&#39;utilisation
WO2017065183A1 (fr) Composé hétérocyclique condensé contenant un groupe oxime ou ses sels, et insecticide agricole et horticole contenant ledit composé et son procédé d&#39;utilisation
WO2016039444A1 (fr) Composé d&#39;imidazopyridazine ou ses sels, insecticide agricole et horticole contenant ledit composé et utilisation associée
WO2017146220A1 (fr) Composé de quinoléine présentant un hétérocycle condensé lié à celui-ci, n-oxyde ou sels correspondants et insecticide agricole et horticole contenant le composé et procédé pour son utilisation
WO2017146221A1 (fr) Composé hétérocyclique condensé présentant des hétérocycles liés et ses sels, insecticide agricole/horticole contenant ledit composé, et procédé d&#39;utilisation dudit insecticide
WO2015072463A1 (fr) Composé amide ou son sel, produit agricole/horticole insecticide/bactéricide contenant ledit composé, et procédé pour son utilisation
WO2017026384A1 (fr) Composé imidazole ou ses sels, et insecticide agricole et horticole contenant ledit composé et son procédé d&#39;utilisation
WO2018124129A1 (fr) Composé hétérocyclique fusionné possédant un groupe oxime ou sels de celui-ci, et pesticide à usage agricole et horticole comprenant ces composés ainsi que procédé de mise en œuvre de ce pesticide
WO2014157600A1 (fr) Composé hétérocyclique condensé ou ses sels, pesticide agricole et horticole contenant ledit composé et son procédé d&#39;utilisation
WO2018084142A1 (fr) Composé de quinoléine ayant un groupe oxime, n-oxyde ou sel de celui-ci, insecticide agricole et horticole le comprenant et son procédé d&#39;utilisation
JP2015003906A (ja) 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2018070502A1 (fr) Composé de 1h-pyrrolopyridine, n-oxyde de celui-ci, sel de celui-ci, pesticide à usage agricole et horticole contenant ledit composé, et son procédé d&#39;utilisation
JP6717968B2 (ja) Ｎ‐アルキルスルホニルインドリン化合物及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
JP6630828B2 (ja) Ｎ‐アルキルスルホニル縮合複素環化合物又はその塩類及び該化合物を含有する殺虫剤並びにその使用方法
WO2018199210A1 (fr) Composé hétérocyclique fusionné ou sel de celui-ci, insecticide agricole et horticole contenant l&#39;un ou l&#39;autre composé et procédé d&#39;utilisation de l&#39;insecticide agricole et horticole
WO2018105632A1 (fr) Composé de quinoléine ayant un groupe carbamate, sel de celui-ci, insecticide pour une utilisation agricole et horticole contenant ledit composé, et utilisation dudit insecticide
WO2018199208A1 (fr) Composé hétérocyclique à noyau à 5 chaînons contenant de l&#39;azote ou sel de celui-ci, insecticide agricole et horticole le contenant, et son procédé d&#39;utilisation
WO2018199209A1 (fr) Composé hétérocyclique ayant un groupe éther d&#39;oxime conjugué ou un sel de celui-ci, insecticide agricole et horticole le comprenant et son procédé d&#39;utilisation
WO2018043597A1 (fr) Composés de 3h-pyrrolopyridine ou de n-oxyde ou de sels de celui-ci, insecticide agricole/horticole contenant lesdits composés, et leur procédé d&#39;utilisation

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17877630

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 17877630

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP