WO2013069771A1 - Dérivé d'acide anthranilique et agent de lutte contre les organismes nocifs - Google Patents

Dérivé d'acide anthranilique et agent de lutte contre les organismes nocifs Download PDF

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WO2013069771A1
WO2013069771A1 PCT/JP2012/079129 JP2012079129W WO2013069771A1 WO 2013069771 A1 WO2013069771 A1 WO 2013069771A1 JP 2012079129 W JP2012079129 W JP 2012079129W WO 2013069771 A1 WO2013069771 A1 WO 2013069771A1
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group
halogen atom
control agent
weight
compounds
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PCT/JP2012/079129
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English (en)
Japanese (ja)
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伸三 利部
正明 三冨
育也 大野
保道 小野▲崎▼
亮 堀越
中村　哲
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Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社
国立大学法人岐阜大学
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Publication of WO2013069771A1 publication Critical patent/WO2013069771A1/fr

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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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to an anthranilic acid derivative and a pest control agent containing the same. More specifically, the present invention relates to an anthranilic acid derivative having a bicyclic to tricyclic fused aromatic heterocycle and a pesticidal agent containing the same.
  • Patent Documents 1 and 2 disclose anthranilic acid-based pest control agents
  • Patent Document 3 discloses a production method thereof. Specific examples of anthranilic acid derivatives having a condensed aromatic heterocycle exhibiting pesticidal activity are disclosed. There is no description.
  • An object of the present invention is to provide a novel compound exhibiting pest control activity.
  • R 1 represents a C 1-8 alkyl group which may be substituted with a halogen atom
  • W each independently represents a halogen atom, a cyano group or a C 1-8 alkyl group which may be substituted with a substituent selected from the group S
  • n represents an integer of 0 to 4
  • A represents a bicyclic to tricyclic fused aromatic heterocycle containing at least one nitrogen atom, which may be substituted with a substituent selected from Group T
  • B represents a 5- to 6-membered aromatic heterocycle optionally substituted with a substituent selected from Group U, which is bonded to the nitrogen atom of A
  • S group consists of a cyano group and a halogen atom
  • T group consists halogen atom, optionally substituted C 1-8 alkyl group and optionally C 1-8 alkyl group optionally substituted by
  • the present invention provides the following [1] to [5].
  • [1] A compound represented by the formula (I).
  • [2] A pest control agent comprising one or more compounds represented by the formula (I).
  • [3] A compound represented by formula (I) for use in pest control.
  • [4] Use of a compound represented by the formula (I) for producing a pest control agent.
  • [5] A method for controlling pests, comprising bringing the compound represented by formula (I) into contact with pests.
  • A is a bicyclic to tricyclic fused pyrrole ring, and B is substituted with a substituent selected from the U group, which is bonded to a nitrogen atom of the fused pyrrole ring.
  • the compound is preferably a pyridine ring or a pyrazine ring optionally substituted with a substituent selected from Group U.
  • the pests to be controlled are preferably agricultural or horticultural pests or animal parasitic pests. That is, the pest control agent is preferably an agricultural or horticultural insecticide or an animal parasite control agent.
  • the compound according to the present invention exhibits excellent pest control activity.
  • the compound according to the present invention is difficult to decrease drug sensitivity, has a high sustained effect, and has high safety during use.
  • halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a chlorine atom or a bromine atom.
  • C 1-8 alkyl group is a chain, branched or cyclic alkyl group having 1 to 8 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms.
  • a C 1-6 alkyl group is more preferably a C 1-4 alkyl group which is an alkyl group having 1 to 4 carbon atoms.
  • Examples of the C 1-8 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, an n-butyl group, an n-pentyl group, a cyclopentyl group, an n-hexyl group, and a cyclohexyl group.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group or a cyclopropyl group and more preferably a methyl group or an isopropyl group.
  • the upper limit of the number of halogen atoms that may be substituted in the “C 1-8 alkyl group optionally substituted with halogen atom” is the number of hydrogen atoms that the alkyl group has, “Atom” and “C 1-8 alkyl group” are as defined above.
  • the C 1-8 alkyl group which may be substituted with a halogen atom is preferably a C 1-6 alkyl group which may be substituted with a halogen atom, more preferably C which may be substituted with a halogen atom. 1-4 alkyl group.
  • the “C 1-8 alkyloxy group” is an alkyloxy group having an alkyl group having 1 to 8 carbon atoms in the form of a chain, branched or cyclic, or a combination thereof, preferably C 1 A -6 alkyloxy group, more preferably a C1-4 alkyloxy group.
  • Examples of the C 1-8 alkyloxy group include a methoxy group, an ethoxy group, and an isopropoxy group, and a methoxy group is preferable.
  • the upper limit of the number of halogen atoms that may be substituted in the “C 1-8 alkyloxy group optionally substituted with halogen atom” is the number of hydrogen atoms that the alkyl group has, “Halogen atom” and “C 1-8 alkyloxy group” are as defined above.
  • the C 1-8 alkyloxy group which may be substituted with a halogen atom is preferably a C 1-6 alkyloxy group which may be substituted with a halogen atom, more preferably a C 1-6 alkyloxy group which may be substituted with a halogen atom.
  • the “aromatic heterocycle” is an aromatic ring containing 1 to 3 atoms arbitrarily selected from a nitrogen atom, an oxygen atom and a sulfur atom as atoms constituting the ring. .
  • the “5- to 6-membered aromatic heterocycle” means an aromatic ring having 5 or 6 atoms constituting the ring in the above-defined “aromatic heterocycle”. It is. A group derived by removing one hydrogen atom from a “5- to 6-membered aromatic heterocycle” may also be referred to as “5- to 6-membered aromatic heterocycle”.
  • a bicyclic to tricyclic condensed aromatic heterocycle containing at least one nitrogen atom means a condensed fragrance formed by sharing a partial bond between two or three aromatic heterocycles or a benzene ring A fused aromatic heterocycle, wherein at least one ring is an aromatic heterocycle containing one or more nitrogen atoms.
  • An aromatic heterocycle containing one or more nitrogen atoms is, for example, a pyrrole ring.
  • a group derived by removing two hydrogen atoms from “a bicyclic to tricyclic fused aromatic heterocycle containing at least one nitrogen atom” is also referred to as “a bicyclic or tricyclic ring containing at least one nitrogen atom”. It may be referred to as a “fused aromatic heterocycle”.
  • the “2- to 3-cyclic fused pyrrole ring” is a condensed aromatic heterocycle containing a pyrrole ring among the above-mentioned “2- to 3-ring fused aromatic heterocycles containing at least one nitrogen atom”. is there.
  • R 1 is a C 1-8 alkyl group optionally substituted with a halogen atom, preferably a C 1-6 alkyl group, more preferably a methyl group, an ethyl group, an n-propyl group, isopropyl Group, cyclopropyl group or t-butyl group.
  • a halogen atom preferably a C 1-6 alkyl group, more preferably a methyl group, an ethyl group, an n-propyl group, isopropyl Group, cyclopropyl group or t-butyl group.
  • W is each independently a halogen atom, a cyano group or a C 1-8 alkyl group optionally substituted with a substituent selected from the S group, and the S group consists of a cyano group and a halogen atom.
  • W is bonded to any position of the 3, 4, 5 or 6 position of the benzene ring.
  • n means the number of W bonded, and is an integer of 0 to 4.
  • Preferred n is an integer of 0-2.
  • A is a bicyclic to tricyclic fused aromatic heterocycle containing at least one nitrogen atom, which may be substituted with a substituent selected from the T group, and the T group includes a halogen atom, a halogen atom A C 1-8 alkyl group which may be substituted with and a C 1-8 alkyloxy group which may be substituted with a halogen atom.
  • A is a divalent group, one bonded to the carbonyl carbon, and one bonded to B through a nitrogen atom.
  • A may be indole diyl group, thienopyrrole diyl group, fluropyrrole diyl group, fluoroindole diyl group, methoxyindole diyl group, chlorothienopyrrole diyl group, pyridinopyrrole diyl group, pyrimidinopyrrole diyl group and benzothieno.
  • Examples thereof include a pyrrole diyl group, preferably a group in which a benzene ring or a 5- to 6-membered aromatic heterocycle is condensed at positions 4 and 5 of the pyrrole-1,2-diyl group or an indole-1,7-diyl group. . More preferably, it is as shown below.
  • B is a 5- to 6-membered aromatic heterocycle optionally bonded to a substituent selected from the U group and bonded to the nitrogen atom of A.
  • the U group is substituted with a halogen atom or a halogen atom. It consists of an optionally substituted C 1-8 alkyl group and an optionally substituted C 1-8 alkyloxy group.
  • B includes, for example, pyridyl group, pyrimidinyl group, pyrazinyl group, pyrazolyl group and thiazolyl group, preferably pyridyl group or pyrazinyl group, more preferably 3-chloro-2-pyridyl group or 3-chloro-2 -A pyrazinyl group.
  • a preferred combination of AB is that A is a bicyclic to tricyclic condensed pyrrole ring, and B may be substituted with a substituent selected from the U group, which is bonded to a nitrogen atom of the condensed pyrrole ring. It is a pyrazine ring optionally substituted with a pyridine ring or a substituent selected from the U group.
  • a more preferable combination of AB is shown below.
  • R 1 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group or a t-butyl group; W is 3-methyl-5-chloro, 3-methyl, 3-methyl-5-bromo or 3-methyl-5-cyano or absent AB is The compound which is is mentioned.
  • the compound represented by the formula (I) can be synthesized as follows.
  • an anthranilic acid derivative represented by the formula (II) and a carboxylic acid represented by the formula (III) are condensed in the presence or absence of a base to give a formula (I ) Can be obtained.
  • Reactions include sulfonate chlorides such as mesyl chloride and tosyl chloride, activators such as triphenylphosphine, trimethylboric acid, diethyl phosphate cyanide and hexachlorocyclotriphosphatriazene or dicyclohexylcarbodiimide and 1-ethyl-3- (
  • a carbodiimide-based compound such as 3′-dimethylaminopropyl) carbodiimide hydrochloride can be used.
  • alkali metal hydrides such as sodium hydride
  • carbonates such as potassium carbonate and sodium carbonate
  • alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
  • tertiary amines such as triethylamine
  • unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine
  • the reaction can be performed without solvent, or using a solvent that does not affect the reaction or a solvent that promotes the target reaction.
  • a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene and Dihalogen hydrocarbons such as dichlorobenzene and solvents such as water can be used alone or in combination of
  • the reaction can usually be carried out at ⁇ 80 to 250 ° C., preferably 20 to 50 ° C.
  • the anthranilic acid derivative represented by the formula (II) can be synthesized by the methods described in Patent Literature 1, Patent Literature 2, and Patent Literature 3, and methods similar thereto.
  • the compound represented by the formula (III) hydrolyzes the compound (VI) obtained by reacting the compound represented by the formula (IV) with the compound represented by the formula (V). Can be obtained.
  • R 2 is a C 1-6 alkyl group
  • X is a halogen atom
  • reaction of the compound represented by the formula (IV) and the compound represented by the formula (V) can be performed in the presence or absence of a base.
  • alkali metal hydrides such as sodium hydride
  • carbonates such as potassium carbonate and sodium carbonate
  • alkali metal hydroxides such as potassium hydroxide and sodium hydroxide
  • tertiary amines such as triethylamine
  • unsubstituted or substituted pyridines such as pyridine and 4-dimethylaminopyridine
  • the reaction may be performed in the presence of copper bromide, potassium bromide, zinc bromide, copper iodide, potassium iodide, zinc iodide or the like.
  • the reaction can be performed using no solvent, a solvent that does not affect the reaction, or a solvent that promotes the target reaction.
  • a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene and One or a combination of two or more halogen hydrocarbons such as dichlorobenzene and water can be used
  • the reaction can usually be carried out at ⁇ 80 to 250 ° C., preferably 20 to 50 ° C.
  • Hydrolysis of the obtained compound represented by the formula (VI) is usually carried out in the presence of a base.
  • the base used include alkali metal alkoxides such as sodium methoxide, potassium methoxide, lithium methoxide and sodium ethoxide, Examples thereof include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and organic bases such as triethylamine and 1,8-diazabicyclo [5.4.0] undec-7-ene, preferably sodium methoxide, Sodium ethoxide or sodium hydroxide.
  • alcohols such as methanol and ethanol
  • ethers such as tetrahydrofuran and dioxane
  • solvents such as water can be used singly or in combination.
  • the compound represented by the formula (IV) can be a commercially available compound, or can be obtained by combining known methods using a commercially available compound as a starting material.
  • a of the compound represented by the formula (IV) represents a group in which a benzene ring or a 5- to 6-membered aromatic heterocycle is condensed at the 4- and 5-positions of the 2-pyrrolyl group
  • Journal of Medicinal Chemistry, 47 (25), 6270-6282 can be synthesized according to the method described in 2004 as shown in the following formula.
  • the compound represented by the formula (VII) (wherein A ′ represents a benzene ring or 5- to 6-membered aromatic heterocycle condensed at the 4- and 5-positions of the 2-pyrrolyl group) is added to the compound represented by the formula (VIII)
  • the above compound can be obtained by reacting the azidoacetate represented by the formula (R 2 is as defined above) and cyclizing the resulting compound represented by the formula (IX).
  • the reaction of the compound represented by the formula (VII) and the compound represented by the formula (VIII) is usually performed in the presence of a base.
  • a base for example, an alkali metal hydride such as sodium hydride, an alkali metal alkoxide such as sodium methoxide, Carbonates such as potassium carbonate and sodium carbonate, alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine or unsubstituted or substituted groups such as pyridine and 4-dimethylaminopyridine.
  • the pyridine which has can be used.
  • the reaction can be performed without solvent, or using a solvent that does not affect the reaction or a solvent that promotes the target reaction.
  • a solvent for example, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, Aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, dichloromethane, chloroform, chlorobenzene and One kind or a combination of two or more kinds of solvents such as halogen hydrocarbons such as dichlorobenz
  • the reaction can usually be carried out at ⁇ 80 to 250 ° C., preferably in the range of ⁇ 20 to 20 ° C.
  • the compound (IV) can be obtained by heating the compound represented by the chemical formula (IX) in the absence of a solvent, in a solvent that does not affect the reaction, or in a solvent that promotes the target reaction.
  • a solvent for example, high boiling point ethers such as diphenyl ether, aromatic hydrocarbons such as benzene, xylene and toluene, saturated hydrocarbons such as heptane, octane, ligroin and mineral oil, chlorobenzene, bromobenzene and di- Halogen hydrocarbons such as chlorobenzene can be used alone or in combination of two or more.
  • the reaction can usually be carried out at 80 to 250 ° C., preferably in the range of 100 to 200 ° C.
  • Examples of the pests that the pest control agent containing one or more compounds represented by the formula (I) exhibit a controlling effect include agricultural and horticultural pests, animal parasitic pests (animal endoparasites and animal ectoparasites) ), Sanitary pests, unpleasant pests, stored / stored food pests and house pests, preferably horticultural pests or animal ectoparasites.
  • insect species are as follows.
  • Agricultural and horticultural pests include lepidopterous pests (for example, Spodoptera litura, Coleoptera, Acayoto, Aomushi, Konaga, Shirouchimojiyoto, Nikameiga, Kononogaiga, Futobikoga, Sakigaiga, Sinkiga, Azalea, Agrotis s.
  • lepidopterous pests for example, Spodoptera litura, Coleoptera, Acayoto, Aomushi, Konaga, Shirouchimojiyoto, Nikameiga, Kononogaiga, Futobikoga, Sakigaiga, Sinkiga, Azalea, Agrotis s.
  • Hemiptera pests eg, peach aphids, cotton aphids, Aphisfabae, corn aphids, pea aphids, potato aphids, bean aphids, tulip beetles ros hum hum avenae, Methopolophium dirhodum, wheat beetle aphid, barley aphid, radish aphid, fake aphid, snowy aphid, Rosy apple aphid, re Aphids (Aphididae, Adelgidae, Phylloxeridae) such as common aphids, Komikan aphids and citrus aphids, leafhoppers such as leafhoppers and leafhoppers, leafhoppers such as leafhoppers, leafhoppers and leafhoppers, Stink bugs such as blue stink bugs and red be
  • animal parasites ie, animal parasites
  • animal ectoparasites include ticks (eg, ticks (eg, Lone Star ticks, Gulf ticks, ticks, Rocky Mountain ticks, West Coast ticks, American dogs) Ticks, ticks, mites, capesid ticks, manes, mites, western mites, shrews, mites, mites, mites, mites, mites, mites, mites, etc.
  • ticks eg, ticks (eg, Lone Star ticks, Gulf ticks, ticks, Rocky Mountain ticks, West Coast ticks, American dogs) Ticks, ticks, mites, capesid ticks, manes, mites, western mites, shrews, mites, mites, mites, mites, mites, mites, etc.
  • Acne mites and cat dust mites cucumber mites (for example, bovine cucumber mites mites), mites mites (for example, bovine mites mites and dog mites mites), Sao Mites (for example, avian mites), worms, mites (for example, chicken mites and mite mites), tsutsugamushi (for example Miyamatsu tsutsugamushi and tsutsugamushi)), fleas (for example, cat fleas, human fleas, mushrooms) Ops murine and mud mines), lice (eg, dog lice and chicken lice), lice (eg, pig lice, dog lice, louse lice, human lice, white lice and bed bugs), house flies, cow flies, sand flies, fly flies (E.g., sand flies), tsetse flies, abs, aedes (e.
  • Animal endoparasites include nematodes (eg, fecal nematodes, helminths, roundworms (eg, tortuous stomach and murine roundworms), ciliate nematodes, and heterocytics (eg, Pig pneumoniae, Cantonese schistosomiasis and cat lungworm), helminths, caecal worms (eg, chicken roundworm), roundworms (eg anisakis nematode, pig roundworm, horse roundworm, dog roundworm and cat roundworm), Rotating nematodes (e.g., bursula, spiny-mouthed jawworm, cat stomachworm, horoscope stomachworm, largemouth horse stomachworm, chicken stomachworm and medinae), filamentous insects (e.g.
  • nematodes eg, fecal nematodes, helminths, roundworms (eg, tortuous stomach and murine roundworms), ciliate nemato
  • Lymphoid worms rotifers and loar worms
  • nematodes and trichinidae for example, Trichuris and Trichinella
  • flukes for example, Schistosoma japonicum and liver fluke
  • bald worms e.g., Lymphoid worms, rotifers and loar worms
  • flukes for example, Schistosoma japonicum and liver fluke
  • bald worms eg, And crustaceans (eg, suspicious leaves (eg, Manson ciliate) and circles (eg, Coleoptera)) and protozoa .
  • Sanitary pests, unpleasant pests, stored grain pests, stored food pests and house pests include mosquitoes (e.g., human striped mosquitoes and mosquitoes), cockroaches (e.g. black cockroaches, crested cockroaches and German cockroaches), coniferous mites (e.g.
  • Flies eg, house flies, fly flies, butterflies, drosophila and chironomids
  • flyfish phylums
  • hymenopteran insects eg, ants such as the black ant and fire ant, bees such as the giant hornet
  • Arthropods eg, Paramecium, Funabushi and Dangamushi
  • Hemiptera insects eg, bed bugs
  • polypods of arthropods eg, centipedes, geese, and millipedes
  • arachnid arthropods E.g., acididae
  • Coleoptera insects e.g., trash
  • Coleoptera arthropods eg, genus Coleoptera
  • earwig insects eg, Carabidae
  • grasshopper insects eg, Crestedidae
  • Coleoptera insects eg, Azuki weevil, scotch beetle,
  • insect species to which the pest control agent of the present invention is applied are lepidopterous insects, hemiptera pests, thrips pests or animal parasitic fleas and mites, more preferably Lepidoptera, Hemiptera pests, Thripidae pests or ticks.
  • the pest control agent of the present invention can use the compound represented by the formula (I) alone or can be prepared using a carrier according to the method of use.
  • the pest control agent of the present invention is an agricultural and horticultural insecticide
  • it is usually mixed with a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant and other formulation adjuvants, It is provided in any dosage form such as emulsion, solution, suspension, wettable powder, flowable, powder, granule, tablet, oil, aerosol or smoke.
  • solid carrier examples include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, and calcium carbonate.
  • liquid carrier examples include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene.
  • alcohols such as methanol, n-hexanol and ethylene glycol
  • ketones such as acetone, methyl ethyl ketone and cyclohexanone
  • aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene.
  • Aromatic hydrocarbons such as, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil And vegetable oils such as cottonseed oil, dimethyl sulfoxide and water.
  • examples of the gaseous carrier include liquefied petroleum gas (LPG), air, nitrogen, carbon dioxide gas, and dimethyl ether.
  • Surfactants or dispersants for emulsification, dispersion or spreading include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters and Examples include lignin sulfonate.
  • examples of the adjuvant for improving the properties of the preparation include carboxymethyl cellulose, gum arabic, polyethylene glycol and calcium stearate.
  • the above carriers, surfactants, dispersants and adjuvants can be used alone or in combination as required.
  • the content of the compound represented by the formula (I) in the preparation is not particularly limited, but is usually 1 to 75% by weight for the emulsion, 1 to 75% by weight for the liquid, and 0.3% for the powder based on the total amount of the preparation. -25% by weight, wettable powder 1-90% by weight, flowable powder 1-90%, granule 0.5-10% by weight.
  • Compounds of formula (I), formulations containing these, and mixtures of these with other pest control agents include harmful insects, plants, plant propagation materials (eg, seeds, plant foliage, roots) , Germinated plants and young plants), soil, nutrient solution in hydroponic culture, solid medium in hydroponic culture, and rooms that need to prevent the invasion of pests. Applied plants include genetically modified crops. These applications can be made before and after pest infestation.
  • the pest control agent of the present invention is an animal parasite control agent
  • it is a solution, emulsion, liquefied drop (pour-on preparation, spot-on preparation, etc.), spray, foam preparation, tablet, granule, fine granule , Powders, capsules, tablets, chewables, injections, suppositories, creams, shampoos, rinses, resins, smokes, poison baits, etc. , Spot-on formulations, etc.).
  • preparations such as ordinary emulsifiers, dispersants, spreading agents, wetting agents, suspending agents, stabilizers, preservatives, propellants, etc.
  • a supplementary agent can be blended, and a normal film forming agent can be blended.
  • Surfactants for emulsification, dispersion or spreading include, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl allyl ethers, polyoxyethylene fatty acid esters, higher alcohols and alkylaryls Examples include sulfonates.
  • Examples of the dispersant include casein, gelatin, polysaccharides, lignin derivatives, saccharides, and synthetic water-soluble polymers.
  • Examples of the spreading / wetting agent include glycerin and polyethylene glycol.
  • Examples of the suspending agent include casein, gelatin, hydroxypropyl cellulose, and gum arabic.
  • Examples of the stabilizer include phenolic antioxidants (such as butylhydroxytoluene (BHT) and butylhydroxyanisole (BHA)), amine-based antioxidants (such as diphenylamine), and organic sulfur-based antioxidants.
  • Examples of preservatives include methyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, and butyl paraoxybenzoate.
  • the above carriers, surfactants, dispersants and adjuvants can be used alone or in combination as required.
  • the liquid agent may further contain a fragrance and a synergist.
  • the content of the compound represented by the formula (I) in the pest control agent of the present invention in the preparation is usually 1 to 75% by weight based on the total amount of the preparation in the liquid preparation.
  • Examples of the carrier used for preparing the cream include non-volatile hydrocarbons (such as liquid paraffin), lanolin-added oils and fats, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils and water. Furthermore, an emulsifier, a humectant, an antioxidant, a fragrance, borax, and an ultraviolet absorber can be used alone or in combination as required. Examples of the emulsifier include fatty acid sorbitan, polyoxyethylene alkyl ether, and fatty acid polyoxyethylene.
  • the content of the compound represented by the formula (I) in the pest control agent of the present invention in the preparation is usually 0.5 to 70% by weight based on the total amount of the preparation.
  • the compound of formula (I) is appropriately subdivided and mixed with a diluent or a carrier such as starch, lactose and talc, and further a disintegrant and binder such as magnesium stearate.
  • a diluent or a carrier such as starch, lactose and talc
  • a disintegrant and binder such as magnesium stearate.
  • it can be manufactured by tableting as necessary.
  • Injections must be prepared as sterile solutions.
  • An injection may contain, for example, sufficient salt or glucose to make the solution isotonic with blood.
  • Carriers that can be used to prepare injectables include glycerides, esters such as benzyl benzoate, isopropyl myristate and fatty acid derivatives of propylene glycol, and organic solvents such as N-methylpyrrolidone and glycerol formal.
  • the content of the compound represented by the formula (I) in the pest control agent of the present invention in the preparation is usually 0.01 to 10% by weight based on the total amount of the preparation for injection.
  • the carrier for preparing the resin agent include vinyl chloride polymers and polyurethane.
  • plasticizers such as phthalates, adipic esters and stearic acid can be added to these substrates as carriers.
  • plasticizers such as phthalates, adipic esters and stearic acid can be added to these substrates as carriers.
  • the compound represented by the formula (I) in the substrate After kneading the compound represented by the formula (I) in the substrate, it can be molded by injection molding, extrusion molding, press molding or the like. Furthermore, it can be made into an animal ear tag or an animal insect repellent collar through suitable processes such as molding and cutting.
  • Carriers for poisonous baits include food and attractants (flours such as wheat flour and corn flour, starches such as corn starch and potato starch, sugars such as granulated sugar, maltose and honey, foods such as glycerin, onion flavor and milk flavor Flavors, animal powders such as rice bran powder and fish meal, and various pheromones).
  • the content of the compound represented by formula (I) in the preparation is usually 0.0001 to 90% by weight based on the total amount of the preparation for poisonous baits.
  • the pest control agent of the present invention can be controlled by being administered orally or by injection into the body of an applied animal, and by being administered to all or part of the body surface of the applied animal.
  • pests can be controlled by coating a place where pests are expected to enter, parasite or move with the pest control agent of the present invention.
  • the pest control agent of the present invention may be used as it is, but depending on the case, it can be diluted with water, a liquid carrier, a commercially available shampoo, rinse, bait or a breeding house underlay.
  • the pest control agent according to the present invention can be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators and fertilizers.
  • Drugs that can be used in combination are those listed in the Pesticide Manual (issued by The 13th Edition The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 13th Edition, 2008, published by SHIBUYA INDEX RESEARCH GROUP). It is done.
  • insecticides, acaricides or nematicides include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenfos ), Pyraclofos, chlorpyrifos-methyl, diazinon, fosthiazate and imicyafos, organophosphate compounds such as methomyl, thiodicarb, aldicarb ( aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran and ben Carbamate compounds such as belfuracarb, nereistoxin derivatives such as cartap and thiocyclam, organochlorine compounds such as dicofol and tetradifon, permethrin, tefluthrin ), Cypermethrin, deltamethrin
  • other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, pyrimidifen, tebufenrad, tebufenrad, tebufenrad, tebufenrad ), Fluacrypyrim, acequinocyl, cyflumetofen, flubendiamide, ethiprole, fipronil, etoxazole, imidacloprid, ididacloprid, imidacloprid, imidacloprid thiamethoxam), acetamiprid (acetamiprid), nitenpyram, thiacloprid, dinotefuran, pime Rosin (pymetrozine), bifenazate, spirodiclofen (spirodiclofen), spiromesifen (spiromesifen), flonicamid (flonicamid),
  • the pest control agent of the present invention can be used in combination with or in combination with microbial pesticides such as BT agents and entomopathogenic virus agents.
  • fungicides used in combination or in combination include strobilurins such as azoxystrobin, kresoxym-methyl, trifloxystrobin, metominostrobin and orysastrobin.
  • strobilurins such as azoxystrobin, kresoxym-methyl, trifloxystrobin, metominostrobin and orysastrobin.
  • Compounds, ananilinopyrimidine compounds such as mepanipyrim, pyrimethanil and cyprodinil, triadimefon, bitertanol, triflumizole, metconazole, protoconazole (Propiconazole), penconazole, flusilazole (flusilazole), microbutanil (myclobutanil), cyproconazole, tebuconazole, hexaconazole (h azole compounds such as exaconazole, prochloraz, simeconazole, quinox
  • ethyl carboxylate was isolated. 100 mg (0.33 mmol) of ethyl 1- (3-chloropyridin-2-yl) -1H-indole-2-carboxylate was dissolved in 2 ml of ethanol, 2 ml of 1N sodium hydroxide was added, and the mixture was refluxed for 30 minutes.
  • the compound represented by the formula (I) was synthesized as follows.
  • Formulation Example 1 [Granule] Compound 1 5% by weight Bentonite 40% by weight Talc 10% by weight 43% by weight of clay 2% by weight calcium lignin sulfonate The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
  • Formulation Example 2 [Granule] Compound 1 2% by weight Sun Extract (trademark) P-252 5% by weight Binder 1.5% by weight Granulation improver 0.5% by weight 91% by weight clay The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
  • Sun Extract (trademark) P-252 is a product of Nippon Paper Chemicals Co., Ltd., mainly composed of sodium lignin sulfonate.
  • Formulation Example 3 [wettable powder] Compound 3 30% by weight 50% by weight of clay 2% white carbon Diatomaceous earth 13% by weight 4% by weight calcium lignin sulfonate Sodium lauryl sulfate 1% by weight The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.
  • Formulation Example 4 [Granule wettable powder] Compound 3 30% by weight 60% clay Dextrin 5% by weight Alkyl maleic acid copolymer 4% by weight Sodium lauryl sulfate 1% by weight The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.
  • Formulation Example 6 Compound 1 15% by weight N, N-dimethylformamide 20% by weight Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight 10% by weight of polyoxyethylene alkyl aryl ether The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 7 [powder] Compound 14 2% by weight 60% clay Talc 37% by weight Calcium stearate 1% by weight The said component was mixed uniformly and the powder agent was obtained.
  • Formulation Example 8 [DL powder] Compound 1 2% by weight DL clay 94.5% by weight 2% white carbon Calcium stearate 1% by weight Light liquid paraffin 0.5% by weight The said component was mixed uniformly and the powder agent was obtained.
  • Formulation Example 9 [Fine Granule F ] Compound 3 2% by weight Carrier 94% by weight 2% white carbon Hysol SAS-296 (JX Nippon Oil & Energy) 2% by weight The said component was mixed uniformly and the powder agent was obtained.
  • Formulation Example 12 [Granule] Compound 1 2% by weight Probenazole 24% by weight Binder 3.0% by weight Granulation improver 0.5% by weight Clay 70.5% by weight The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
  • Test Example 1 Cutout of a leaf disc having a diameter of 5.0 cm from cabbage cultivated in a potter's beak prevention test pot, and a chemical solution of a compound having a predetermined concentration prepared to be 50% acetone water (0.05% Tween 20 (trademark) added). Sprayed. After air drying, the second instar larvae were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
  • Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead insects) ⁇ ⁇ 100
  • the compounds 1, 2, 3, 4, 5, 6, 7, 8, 26 and 28 showed insecticidal activity with a mortality rate of 80% or more after 100 ppm of foliage treatment.
  • compounds 1,3,4,5,6,7,8,9,10,18,19,20,22,23,24 and 26 show insecticidal activity with a death rate of 80% or more. It was.
  • With 1 ppm foliar treatment compounds 1, 4, 5, 6, 7, 8, 11, 12, 13, 14, 15, 16, 18, 19, 22, 23, 24, and 28 have a death rate of 80% or more. Insecticidal activity was demonstrated.
  • Test Example 2 A cut-out leaf disc having a diameter of 5.0 cm was cut out from a cabbage grown in a pot- spotted carp control pot, and a chemical solution of a compound having a predetermined concentration prepared so as to be 50% acetone water (added with 0.05% Tween 20 (trademark)). Sprayed. After air-drying, the third-instar larvae of Spodoptera litura were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
  • Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead insects) ⁇ ⁇ 100
  • the compounds 1,3,4,5,6,7,8,25,26 and 28 showed insecticidal activity with a mortality rate of 80% or more after 100 ppm of foliage treatment.
  • Insecticidal activity of compounds 1,3,4,5,6,7,8,9,10,18,19,20,21,22,23,23, and 26 with a death rate of 80% or more by treatment with 10 ppm of foliage showed that.
  • Compound 1,3,4,5,6,7,8,9,11,12,14,16,18,19,20,22,23,24 and 28 were killed by 1 ppm of foliage at 80% death rate The above insecticidal activity was exhibited.
  • Test Example 3 Cotton Aphid Control Test A leaf disc having a diameter of 2.0 cm was cut out from a cucumber cultivated in a pot, and 50% acetone water (0.05% Tween 20 (trademark) added) was added to this. The chemical solution was sprayed. After air drying, cotton aphid first instar larvae were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
  • Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead insects) ⁇ ⁇ 100
  • the compounds 1, 5, 6, 7, 8, 11, 12, 13, 14, 15, 16, 18, and 28 showed insecticidal activity with a mortality rate of 80% or more after treatment with 500 ppm of foliage.
  • Compounds 1, 5, 6, 7, 8, 11, 12, 13, 14, 19, 20, and 28 showed insecticidal activity with a mortality rate of 80% or more after 100 ppm foliage treatment.
  • Compounds 5, 6, 7, 8, 9, 12, 14, 19, 20, 22, 24, and 28 showed insecticidal activity with a mortality rate of 80% or more after treatment with 20 ppm of foliage.
  • Citrus thrips control test A leaf disk with a diameter of 2.8 cm was cut out from green beans grown in pots, and 50% acetone water (0.05% Tween20 (trademark) added) was added to this compound. The chemical solution was sprayed. After air drying, the first instar larvae of Citrus thrips were released. Thereafter, this was left in a thermostatic chamber (16 hours light period-8 hours dark period) at 25 ° C. The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. The test was conducted by a two-run system.
  • Death rate (%) ⁇ Number of dead insects / (Number of living insects tens of dead insects) ⁇ ⁇ 100
  • the compounds 1, 5, 6, 8, 11, 12, 13, 14, 15, and 22 exhibited insecticidal activity with a mortality rate of 80% or more after treatment with 500 ppm of foliage.
  • Compounds 6, 7, 19 and 28 showed insecticidal activity with a mortality rate of 80% or more after 100 ppm foliage treatment.
  • Test Example 5 1 ⁇ L of a chemical solution of a compound prepared at a predetermined concentration with acetone was treated on the back of a female housefly of a housefly kept in a housefly control test room. After the chemical treatment, adults were transferred to plastic cups so that there were 5 per cup, and left in a constant temperature room (16 hours light period-8 hours dark period) at 25 ° C. After 24 hours of treatment, the state of agony of adults was observed, and the rate of agony was calculated according to the following formula. The test was conducted by a two-run system.
  • Rate of bitter worms (%) ⁇ number of bitter worms / (number of normal worms + number of bitter worms) ⁇ ⁇ 100
  • the compounds 6, 9, 10, 19, 22, and 23 showed a high insecticidal effect with an morbidity rate of 80% or more at a treatment amount of 2 ⁇ g of compound per head.

Abstract

L'invention concerne un composé représenté par la formule (I) qui a une excellente activité de lutte contre les organismes nocifs. [R1 représente un groupe alkyle en C1-8 ou similaire ; W représente un atome d'halogène ou similaire ; n représente un entier de 0 à 4 ; A représente un hétérocycle aromatique condensé bicyclique à tricyclique contenant au moins un atome d'azote, ou similaire ; et B représente un hétérocycle aromatique à 5 à 6 chaînons qui est lié à un atome d'azote dans A.]
PCT/JP2012/079129 2011-11-11 2012-11-09 Dérivé d'acide anthranilique et agent de lutte contre les organismes nocifs WO2013069771A1 (fr)

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