WO2019163921A1 - Composé de pyridine substitué et sel de celui-ci - Google Patents

Composé de pyridine substitué et sel de celui-ci Download PDF

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Publication number
WO2019163921A1
WO2019163921A1 PCT/JP2019/006661 JP2019006661W WO2019163921A1 WO 2019163921 A1 WO2019163921 A1 WO 2019163921A1 JP 2019006661 W JP2019006661 W JP 2019006661W WO 2019163921 A1 WO2019163921 A1 WO 2019163921A1
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Prior art keywords
formula
compound
alkyl
alkylthio
salt
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PCT/JP2019/006661
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English (en)
Japanese (ja)
Inventor
哲夫 米田
優太 田澤
達也 可児
洋子 長
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石原産業株式会社
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Publication of WO2019163921A1 publication Critical patent/WO2019163921A1/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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel substituted pyridine compound or a salt thereof.
  • the present invention also relates to pesticides, agricultural and horticultural insecticides, acaricides, nematicides or soil-killing pesticides containing a substituted pyridine compound or a salt thereof as an active ingredient. Furthermore, the present invention relates to a method for controlling pests by applying an effective amount of a substituted pyridine compound or a salt thereof.
  • Patent Document 1 describes a wide range of amide compounds for pharmaceutical use, but there is only a specific description of R 4 as a hydrogen atom in the following formula (I).
  • Patent Document 2 describes a wide range of amide compounds for pharmaceutical use, but there is only a specific description in which R 4 is piperidine in the following formula (I).
  • An object of the present invention is to provide a compound or a salt thereof highly active against pests, a pest control agent containing the compound or a salt thereof as an active ingredient, for example, agricultural and horticultural insecticides, acaricides It is to provide a nematicide or a soil-killing pesticide, and to provide a method for controlling pests by applying the compound or a salt thereof.
  • the present inventors have conducted various studies on substituted pyridine compounds in order to find better pest control agents. As a result, the present inventors have found that a novel substituted pyridine compound or a salt thereof has a high control effect against pests with a low dose, and completed the present invention.
  • A is a substituent represented by the formula (A-1) or a substituent represented by the formula (A-2);
  • R 3 is a hydrogen atom, alkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio) carbonyl or carboxyl.
  • R 1 is a hydrogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyl, cycloalkyl, cycloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio;
  • R 2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or dialkylamino;
  • m is an integer from 0 to 2; When m is 2, R 2 may be the same or different.
  • A is a substituent represented by the formula (A-1) or a substituent represented by the formula (A-2);
  • R 3 is a hydrogen atom, alkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 ′ is nitro, halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, (alkylthio) carbonyl or carboxyl.
  • R 1 is a hydrogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyl, cycloalkyl, cycloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or haloalkylthio;
  • R 2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or dialkylamino;
  • m is an integer from 0 to 2; when m is 2, each R 2 may be the same or different; However, when R 4 ′ is bromine, R 1 is not a hydrogen atom.
  • a pesticide containing a substituted pyridine compound represented by the formula (1) or a salt thereof as an active ingredient for example, agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide), and formula (I ′)
  • the present invention relates to a method for controlling pests by applying an effective amount of a compound represented by the formula:
  • a highly active compound for pests or a salt thereof is provided, and a pest control agent containing the compound or a salt thereof as an active ingredient, for example, agricultural and horticultural insecticides, acaricides It is possible to provide a nematicide or a soil-killing pesticide, and a method for controlling pests by applying the compound or a salt thereof.
  • C n (n is a natural number) is synonymous with “carbon number n” (n is a natural number).
  • ppm is described as the concentration, it indicates “ppm by weight”.
  • the present invention relates to a substituted pyridine compound represented by the formula (I) or a salt thereof.
  • the present invention also provides a pesticide containing a substituted pyridine compound represented by the formula (I ′) or a salt thereof as an active ingredient (for example, agricultural and horticultural insecticides, acaricides, nematicides or insecticides). And a method for controlling pests by applying an effective amount of the compound or a salt thereof.
  • “compound of formula X” means “compound of formula X”.
  • haloalkyl in the formula (I) or the formula (I ′) means an alkyl in which at least one hydrogen atom contained in the alkyl is substituted with a halogen atom.
  • haloalkoxy or haloalkylthio means alkoxy or alkylthio in which at least one hydrogen atom contained in each group is substituted with a halogen atom, respectively.
  • a halogen atom substituted from a hydrogen atom is referred to as “halogen as a substituent”.
  • the number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • alkyl or alkyl moiety in the formula (I) or the formula (I ′) include, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, Examples thereof include linear or branched C 1 -C 6 groups such as normal hexyl or neohexyl.
  • alkenyl or alkenyl moiety in the formula (I) or the formula (I ′) include, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl. 2-methyl-2-propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl or 2 And a straight or branched C 2 -C 6 group such as 1,3-dimethyl-2-butenyl.
  • alkynyl or alkynyl moiety in the formula (I) or the formula (I ′) include, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- Linear or branched C such as propynyl, 2-methyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl or 5-hexynyl group 2 -C 6 thereof.
  • Examples of the cycloalkyl or cycloalkyl moiety in the formula (I) or the formula (I ′) include C 3 -C 6 groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Examples of the salt of the compound of the formula (I) or the formula (I ′) include any salt as long as it is acceptable in the technical field, and examples thereof include ammonium salts such as dimethylammonium salt and triethylammonium salt.
  • Inorganic salts such as hydrochloride, perchlorate, sulfate, nitrate; organic acid salts such as acetate, trifluoroacetate, oxalate, p-toluenesulfonate, methanesulfonate, etc. Is mentioned.
  • the compound of the formula (I) or a salt thereof and the compound of the formula (I ′) or a salt thereof there may be an isomer such as an optical isomer. Both isomeric mixtures are included.
  • isomers are described as a mixture.
  • the present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.
  • the chemical structure may be different from that of the compound of formula (I) or formula (I ′). Since it can be recognized, it is clear that it is within the scope of the present invention.
  • the compound of formula (I) or formula (I ′) or a salt thereof (hereinafter also referred to as the compound of the present invention) can be produced according to the following production method and / or a usual salt production method. It is not limited to these methods. Incidentally, the production method of the following preparation and intermediates have been described for the preparation of compounds of formula (I), according to these processes, by using a compound having a R 4 'in place of R 4, Compounds of formula (I ′) can be prepared.
  • the compound of the formula (I) can be produced by reacting the compound of the formula (II) with the compound of the formula (III) in the presence of a dehydration condensing agent or a base.
  • the compound of Formula (II) or the compound of Formula (III) can be manufactured by a well-known method besides using a commercial item.
  • the dehydrating condensing agent is not particularly limited.
  • the base is not particularly limited.
  • tertiary amines such as triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4- (dimethyl Amino) pyridine, 2,6-lutidine and the like.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • a solvent include, but are not limited to, ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane, and dimethoxyethane; aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethane, and chloroform Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane Nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of formula (I) can be produced by reacting the compound of formula (II-a) with the compound of formula (III) in the presence of a base.
  • the base may be an organic base or an inorganic base.
  • the organic base is not particularly limited, and examples thereof include amine bases such as triethylamine and diisopropylethylamine.
  • the inorganic base is not particularly limited, and examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate.
  • the reaction can be performed in the presence of a solvent, if necessary. Although it does not restrict
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of the formula (II-a) can be a commercially available product or can be produced by reacting the compound of the formula (II) with a halogenating agent.
  • the halogenating agent is not particularly limited, and examples thereof include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, and phosphorus pentachloride.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited, but ethers such as diethyl ether, butyl methyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, 1,4-dioxane and dimethoxyethane; aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethane and chloroform Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hex
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of the formula (III) can be produced by reacting the compound of the formula (III-a) with the compound of the formula (IV).
  • the compound of formula (III-a) or the compound of formula (IV) can be produced by a known method in addition to using a commercially available product.
  • the reaction can be performed in the presence of a base as necessary.
  • a base examples include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
  • alkali metal hydrides such as sodium hydride
  • alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
  • Tertiary amines such as triethylamine, 4-methylmorpholine, diisopropylethylamine; 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4- (dimethylamino) pyridine, 2,6- Lutidine and the like.
  • the reaction can be performed in the presence of a solvent, if necessary. Although it does not restrict
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the pest control agent containing the compound of the present invention as an active ingredient is, for example, a pest, mite, nematode or soil pest control agent that is a problem in the field of agriculture and horticulture, that is, an agricultural and horticultural insecticide, acaricide or nematicide. It is useful as an agent or a soil killing insect pest. It is also useful as an animal parasite control agent, that is, an animal killing parasite agent.
  • the compound of the present invention comprises aphids such as peach aphid, cotton aphid, etc .; Agriculture such as leafhoppers, leafhoppers, scale insects, stink bugs, whiteflies such as tobacco whiteflies, thrips, grasshoppers, fly flies, scarabs, cornworms, cabrayaga, ants, etc.
  • the agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention as an active ingredient is used for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes, etc. It is particularly effective. Among them, it is very useful as an insecticide or acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests.
  • agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention as active ingredients are drugs such as organic phosphorus agents, carbamate agents, synthetic pyrethroid agents, neonicotinoid agents, etc. It is also effective for the control of various resistant insect pests.
  • the compound of the present invention has excellent osmotic migration, an agricultural / horticultural insecticide, acaricide, nematicide or soil-killing pesticide containing the compound of the present invention as an active ingredient is added to the soil.
  • an agricultural / horticultural insecticide, acaricide, nematicide or soil-killing pesticide containing the compound of the present invention as an active ingredient is added to the soil.
  • By the treatment it is possible to control pests of the foliage at the same time as the control of soil harmful insects, mites, nematodes, gastropods and the like.
  • the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests and the like are comprehensively included.
  • Examples include agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides to be controlled.
  • the pest control agent containing the compound of the present invention as an active ingredient is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oil suspension by mixing the compound and various adjuvants. It is used in various forms such as pharmaceuticals, aqueous granules, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc., but as long as it meets the purpose of the present invention, it is usually used in this field. It can be in any formulation form.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water, Solvents such as toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkylsulfate esters, alkylsulfates, alkylarylsulfates, al
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the art.
  • a bulking agent for example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction.
  • Various commonly used adjuvants such as agents and antifungal agents can also be used.
  • the compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, desirably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the application of the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application place, type of pests and occurrence, etc., but generally 0.05 to 800,000 ppm, preferably 0.5 to
  • the active ingredient concentration is 500,000 ppm
  • the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare.
  • the present invention also includes a method for controlling pests, mites, nematodes or soil pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • Application of various preparations of the pest control agent containing the compound of the present invention as an active ingredient, or dilutions thereof, is generally performed by a commonly used application method, that is, spraying (for example, spraying, misting, atomizing, dusting). Granule, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra-low volume application method. In this method, it is possible to contain 100% of the active ingredient.
  • the agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention as an active ingredient may be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. In this case, even more excellent effects and functions may be exhibited.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. .
  • an insecticidal composition, an acaricidal composition, a nematicidal composition or a composition for soil-killing insect pests in which the compound of the present invention and one or more active ingredient compounds of other agricultural chemicals are mixed or used in combination.
  • the product can improve the application range, the timing of chemical treatment, the control activity, and the like in a preferable direction.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately in the form of a mixture, or both may be used together.
  • the present invention includes such an insecticidal composition, an acaricidal composition, a nematicidal composition or a soil-killing insect pest composition.
  • the compound of the present invention is a crystalline protein toxin produced by Bacillus thuringiensis such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, entomopathogenic virus agent, entomopathogenic fungus agent, Microbial pesticides such as pathogenic fungi; avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE -175, antibiotics such as abamectin, emamectin, spinetoram and semi-synthetic antibiotics; natural products such as azadirachtin, rotenone; Repellents like Can be an equal, mix, also it is
  • an active ingredient compound for example, mepanipyrim, pyrimethanil, cyprodinil ), Anilinopyrimidine compounds such as ferimzone; Tria such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
  • a substituted pyridine compound represented by the formula (I) or a salt thereof (2) The compound or salt thereof according to (1), wherein R 1 is a hydrogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylcarbonyl. (3) The compound or salt thereof according to (1) or (2), wherein R 1 is a hydrogen atom, alkyl, haloalkyl, alkoxy or alkylcarbonyl.
  • a pest control agent comprising the substituted pyridine compound represented by the formula (I ′) or a salt thereof as an active ingredient.
  • Synthesis example 1 Synthesis of methyl 4- (2- (trifluoromethyl) pyrimidine-5-carboxamide) nicotinate (compound No. Ia-5) 2- (trifluoromethyl) pyrimidine-5-carboxylic acid (0.25 g), 4- Methyl amino-nicotinate (0.20 g), O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate (0.60 g), Triethylamine (0.55 mL) was dissolved in tetrahydrofuran (3.0 mL) and stirred at room temperature for 18 hours.
  • reaction mixture was poured into water and extracted with ethyl acetate.
  • the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure.
  • the residue was purified by flash chromatography (eluent: n-heptane / ethyl acetate) to obtain the desired product (0.24 g, yield 56%).
  • Synthesis example 2 Synthesis of methyl 4- (5- (trifluoromethyl) pyrazine-2-carboxamide) nicotinate (Compound No. Ib-5) 5- (trifluoromethyl) pyrazine-2-carboxylic acid (0.11 g), 4- Methyl amino-nicotinate (80 mg), O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate (0.40 g), triethylamine ( 0.22 mL) was dissolved in N, N-dimethylformamide (3.5 mL) and stirred at room temperature for 24 hours.
  • reaction mixture was poured into water and extracted with ethyl acetate.
  • the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure.
  • the residue was purified by flash chromatography (eluent: n-heptane / ethyl acetate) to obtain the desired product (90 mg, yield 52%).
  • Synthesis example 3 Synthesis of methyl 4- (N-methyl-5- (trifluoromethyl) pyrazine-2-carboxamide) nicotinate (Compound No. Ib-10) 5- (Trifluoromethyl) pyrazine-2-carboxylic acid (0.10 g ) In tetrahydrofuran (5 mL) at 0 ° C. was added oxalyl chloride (0.13 mL) and 1 drop of N, N-dimethylformamide. The reaction mixture was stirred at room temperature for 2 hours. The solvent and excess reagent were then removed under reduced pressure.
  • Tables 1 and 2 typical examples of the compounds of the present invention are listed in Tables 1 and 2. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • Tables 1 and 2 the numerical values described in the physical properties column indicate melting points (° C.), and the compounds described as “NMR” have their 1 H-NMR spectrum data in Tables 3 to 6. Show.
  • Tables 1 to 6 No. represents a compound number.
  • Me is a methyl group
  • Et is an ethyl group
  • n-Pr is a normal propyl group
  • t-Bu is a tertiary butyl group
  • i-Pr is an isopropyl group
  • c-Pr is cyclopropyl.
  • N-Bu represents a normal butyl group
  • i-Bu represents an isobutyl group
  • s-Bu represents a secondary butyl group.
  • Test Example 1 Effect test on green planthopper Rice seedlings were immersed in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. In this, about 10 larvae of 2 to 3 years old were released, and the tube mouth was covered with gauze and allowed to stand in a constant temperature room at 25 ° C. Five days after the treatment, the survival of the brown planthopper was determined, and the death rate (%) was determined by the following formula. In addition, as this invention compound, said compound No.
  • Mortality rate (%) (number of dead insects / number of released insects) x 100
  • Test Example 2 Effect test on tobacco whitefly An adult tobacco whitefly was released on a pot-planted cucumber seedling. After laying eggs for one day, cucumber seedlings were taken out and placed in a constant temperature room with illumination at 25 ° C. Seven days later, the number of 1-2 instar larvae parasitizing the cucumber seedlings was examined, and a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm was sprayed using a hand spray. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control value was determined by the following formula. In addition, as this invention compound, said compound No.
  • Control value (1 ⁇ (Ta ⁇ Cb) / (Tb ⁇ Ca)) ⁇ 100
  • Ta Number of old larvae after treatment in treated cucumber seedling
  • Tb Number of first to second larvae before treatment in treated cucumber seedling
  • Ca Number of old larvae after treatment in untreated cucumber seedling
  • Cb Before treatment in untreated cucumber seedling Number of larvae 1-2
  • Test Example 3 Effect test on peach aphid
  • Five adult peach aphids were released on radish leaves inserted in test tubes. After removing adults one day later, the number of larvae parasitizing on radish leaves was counted and immersed in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. In addition, as this invention compound, said compound No.
  • Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
  • Formulation Example 3 (1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
  • Formulation Example 7 (1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain a liquid agent.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dentistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne : un composé de pyridine substitué représenté par la formule (I) ou un sel de celui-ci ; un agent de lutte contre des organismes nuisibles contenant un composé de pyridine substitué représenté par la formule (I') ou un sel de celui-ci en tant que principe actif ; un insecticide agricole et horticole, un acaricide, un nématocide, ou un agent de lutte contre des organismes nuisibles du sol contenant un composé de pyridine substitué représenté par la formule (I') ou un sel de celui-ci en tant que principe actif ; et un procédé de lutte contre des organismes nuisibles par l'application d'un composé de pyridine substitué représenté par la formule (I') ou d'un sel de celui-ci. (Chacun des substituants dans la formule (I) et la formule (I') sont tels que définis dans la spécification.)
PCT/JP2019/006661 2018-02-22 2019-02-21 Composé de pyridine substitué et sel de celui-ci WO2019163921A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003048878A (ja) * 2001-05-31 2003-02-21 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2006008675A (ja) * 2004-05-27 2006-01-12 Nippon Nohyaku Co Ltd 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
JP2016020335A (ja) * 2014-06-19 2016-02-04 石原産業株式会社 有害生物防除剤
WO2017222037A1 (fr) * 2016-06-24 2017-12-28 石原産業株式会社 Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif
WO2018199175A1 (fr) * 2017-04-27 2018-11-01 石原産業株式会社 Composé n-(4-pyridyl) nicotinamide ou sel de celui-ci

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003048878A (ja) * 2001-05-31 2003-02-21 Nippon Nohyaku Co Ltd 置換アニリド誘導体、その中間体及び農園芸用薬剤並びにその使用方法
JP2006008675A (ja) * 2004-05-27 2006-01-12 Nippon Nohyaku Co Ltd 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
JP2016020335A (ja) * 2014-06-19 2016-02-04 石原産業株式会社 有害生物防除剤
WO2017222037A1 (fr) * 2016-06-24 2017-12-28 石原産業株式会社 Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif
WO2018199175A1 (fr) * 2017-04-27 2018-11-01 石原産業株式会社 Composé n-(4-pyridyl) nicotinamide ou sel de celui-ci

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