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WO1999044993A1 - Compose a base d'acryronitrile, son procede de production et agent de lutte contre les ravageurs renfermant ce compose - Google Patents

Compose a base d'acryronitrile, son procede de production et agent de lutte contre les ravageurs renfermant ce compose Download PDF

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Publication number
WO1999044993A1
WO1999044993A1 PCT/JP1999/001047 JP9901047W WO9944993A1 WO 1999044993 A1 WO1999044993 A1 WO 1999044993A1 JP 9901047 W JP9901047 W JP 9901047W WO 9944993 A1 WO9944993 A1 WO 9944993A1
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Prior art keywords
substituted
optionally substituted
compound
cosme
heterocyclic group
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PCT/JP1999/001047
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English (en)
Japanese (ja)
Inventor
Toru Koyanagi
Yuji Nakamura
Masayuki Morita
Tsuyoshi Ikeda
Original Assignee
Ishihara Sangyo Kaisha Ltd.
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Priority to AU32748/99A priority Critical patent/AU3274899A/en
Publication of WO1999044993A1 publication Critical patent/WO1999044993A1/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
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • the present invention relates to a novel acrylonitrile compound useful as an active ingredient of a pesticide.
  • U.S. Pat. No. 3,337,565 and U.S. Pat. No. 3,337,566 disclose an acrylonitrile derivative similar to the compound of the present invention, and the derivative and the compound of the present invention have different chemical structures. I do.
  • WO97 / 40009 describes an ethylene derivative similar to the compound of the present invention, but the derivative and the compound of the present invention have different chemical structures.
  • WO098 / 42683 describes a triazole compound power 5 'similar to the compound of the present invention.
  • the compound and the compound of the present invention have different chemical structures.
  • the present invention provides a compound represented by the formula (I):
  • Q is an optionally substituted phenyl, an optionally substituted benzyl, an optionally substituted naphthyl or 1 J
  • X is an optionally substituted naphthyl or 1 J
  • R 2 is alkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, substitution which may be alkoxy, substituted Alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkylthio, optionally substituted alkenylthio, optionally substituted alkynylthio, optionally substituted cycloalkyl, optionally substituted ⁇ cycloalkyloxy, cycloalkylthio which may be substituted, phenyl which may be substituted, phenoxy which may be substituted, phenylthio which may be substituted, benzyl which may be substituted, benzyl which may be substituted Benzyloxy, optionally substituted benzylthio,
  • R 3 is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted Is a benzyl or 1 J, wherein J is a 5- or 6-membered heterocyclic group containing at least one kind of 1 to 4 atoms selected from the group consisting of 0, S and N.
  • a 6- to 11-membered condensed heterocyclic group containing at least one atom selected from the group consisting of 0, S and N condensed heterocyclic groups are substituted Wherein X does not contain a pyridyl group], an acrylonitrile compound or a salt thereof, a production method thereof, and a pesticide containing the same.
  • R 2 optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted Good alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkylthio, optionally substituted alkenylthio and optionally substituted alkynylthio, and optionally substituted alkyl of R 3 , substituted
  • substituent of alkenyl and alkynyl which may be substituted include nodogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, nitro, cyano, and amino.
  • the number of substitutions may be one or more, and when two or more, they may be the same or different.
  • W 2 is a halogen, an alkyl, a noroalkyl, an alkoxy, a haloalkoxy, an alkylthio, a haloalkylthio, a phenyl, a nitro or a cyano.
  • R 2 of a substituted or unsubstituted cycloalkyl as the substituent of the optionally substituted cycloalkyl good cycloalkylthio and R 3 may be substituted which may cycloalkyl O carboxymethyl ⁇ beauty substituted, for example halogen, Alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, cyano and the like.
  • the number of substitutions may be one or more, and in the case of two or more, they may be the same or different.
  • heterocyclic group of J examples include pyrrolyl, furyl, phenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3- Oxadiazolyl, 1,2,4 Oxadiazolyl, 1,3,4 Oxadiazolyl, 1,2,3_thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3,4-tetra Zolyl, pyridyl, pyrimidinyl, birazinyl, pyridazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, imidazolinyl, birazolinyl , Oxazolinyl, isooxazolinyl,
  • Examples include sobenzofuranyl, benzothenyl, benzimidazolyl, indazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, quinolyl, isoquinolyl, cinnolyl, phthalazyl, quinazalinyl, and quinoxalinyl.
  • the alkyl or alkyl moiety as a substituent contained in R 2 , R 3 or J is a straight-chain or branched one having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl and the like.
  • R P alkenyl contained in R 2 or R 3, alkynyl, alkenyl moiety or alkynyl moiety, or Q, X, alkenyl as a substituent contained in R 2, R 3 or J, alkenyl moiety, alkynyl or alkynyl moiety Examples thereof include linear or branched ones having 2 to 6 carbon atoms, for example, vinyl, aryl, butadienyl, isopropyl, ethynyl, propynyl, 2-penten-4-ynyl and the like.
  • the cycloalkyl or cycloalkyl moiety contained in R 2 or R 3 or the cycloalkyl as a substituent contained in Q, X, R 2 , R 3 or J has 3 to 6 carbon atoms, for example, cyclopropyl , Cyclopentyl, cyclohexyl and the like.
  • halogen as a substituent contained in Y or halogen as a substituent contained in Q, X, R 2 , R 3 or J is an atom of fluorine, chlorine, bromine or iodine.
  • the number of halogen substituents as a substituent may be 1 or 2 or more. In the case of 2 or more, they may be the same or different.
  • Acrylonitrile compounds of the formula (I) are possible force to form a salt, is a salt thereof forces such as the hydrochloride salt include everything force 5 'so long as it is agriculturally acceptable, sulfate, inorganic acid salts such as nitrates;? acetates, and organic acid salts force be mentioned up as main evening Nsuruhon acid salt.
  • the acrylonitrile compound of the formula (I) has a geometrical isomer (E-form and Z-form), and the present invention includes all of these isomers and mixtures thereof.
  • the optical isomer force 'existing force 5 ' may be used. And mixtures thereof.
  • Desirable compounds among the acrylonitrile compounds of the formula (I) or salts thereof are as follows.
  • the heterocyclic group of J is pyrrolyl, furyl, chenyl, imidazolyl, vilazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3 —Oxadizazolyl, 1,2,4-oxodazolyl, 1,3,4-thoxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3 , 4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, imidazolinyl , Virazolinyl, oxa
  • R 2 is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted alkoxy, an optionally substituted alkenyloxy, Alkynyloxy, alkylthio which may be substituted, alkylthio which may be substituted, alkenylthio which may be substituted, cycloalkyl which may be substituted, cycloalkyl which may be substituted, cycloalkyloxy which may be substituted An optionally substituted cycloalkylthio, an optionally substituted phenyl, an optionally substituted phenoxy, an optionally substituted phenylthio, an optionally substituted benzyl, an optionally substituted
  • the heterocyclic group of J is pyrrolyl, furyl, phenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3 —Oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3,4 —Tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, imidazolinyl, Birazolinyl, oxazolinyl, is
  • S- is J, 3 months optionally substituted alkyl, alkenyl which may be substituted, substitution which may be alkynyl, optionally substituted cycloalkyl, optionally benzyl substituted or mono- J
  • a 6- to 11-membered condensed heterocyclic group containing at least one kind of atom selected from the group consisting of S and N, wherein the condensed heterocyclic group may be substituted.
  • the heterocyclic group of J is pyrrolyl, furyl, chenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,3 —Oxadiazolyl, 1,2,4-oxodazolyl, 1,3,4-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3,4 —Tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, imidazolinyl, Birazolinyl, oxazolinyl
  • the acrylonitrile-based compound of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced, for example, according to the reaction [A], [B] and a usual method for producing a salt.
  • reaction [A] is described below.
  • Q, X, Y and the formula (I) are as described above, and L is a halogen.
  • Bases include, for example, alkali metals such as sodium and potassium; alcoholates of alkali metals such as potassium tert-butoxide; carbonates such as potassium carbonate and sodium carbonate; potassium bicarbonate and sodium bicarbonate.
  • Bicarbonates such as thorium; metal hydroxides such as potassium hydroxide and sodium hydride; metal hydrides such as potassium hydride and sodium hydride; trimethylamine, triethylamine, pyridine, 4-dimethyl One or more tertiary amines such as aminopyridine are appropriately selected.
  • Reaction [A] is performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; E-carbon chloride, methyl chloride, chloroform, and dichloromethane.
  • Cyclic or acyclic aliphatic hydrocarbons such as dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and getyl ether; esters such as methyl acetate and ethyl acetate
  • Apolar aprotic solvents such as dimethyl sulfoxide, sulfolane, N, N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, pyridine; acetonitrile, pionitrile Nitriles such as acrylonitrile; acetone, methylethylketo
  • ketones such as tertiary amines such as trimethylamine and triethylamine; water and the like.
  • the reaction temperature of the reaction [A] is usually from 180 to 150 ° C (: desirably from 150 to 120 ° C), and the reaction time is usually from 0.1 to 48 hours, preferably from 0.2 to 24 hours.
  • the reaction time is usually from 0.1 to 48 hours, preferably from 0.2 to 24 hours.
  • reaction [B] is described below.
  • the first step of the reaction [B] is performed in the presence of a base, if necessary.
  • a base one or more tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine are appropriately selected.
  • the first step of the reaction [B] is usually performed in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; carbon tetrachloride, methyl chloride, and chloroform.
  • Cyclic or acyclic aliphatic hydrocarbons such as dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, and getyl ether; esters such as methyl acetate and ethyl acetate One or two or more are appropriately selected from the above.
  • the reaction temperature of the first step of the reaction (B) is usually from 1 to 80 to + 150 ° C, preferably from 1 to 50 to + 80 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0. In 5-24 hours is there.
  • the compound represented by the formula (V) ′ prepared in the first step of the reaction [B] is a novel useful intermediate compound in the present invention.
  • the second step of the reaction [B] is performed in the presence of a base, if necessary.
  • a base include one or more of tertiary amines such as carbonates such as potassium carbonate and sodium carbonate; tertiary amines such as trimethylamine, triethylamine, pyridine and 4-dimethylaminopyridine. It is appropriately selected.
  • the second step of the reaction [B] is usually performed in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; carbon tetrachloride, methyl chloride, and chloroform.
  • Cyclic or acyclic aliphatic hydrocarbons such as dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, and getyl ether; esters such as methyl acetate and ethyl acetate One or two or more of nitriles such as acetonitrile, propionitrile and acrylonitrile; and ketones such as acetone and methylethylketone are appropriately selected.
  • the reaction temperature of the second step of the reaction (B) is usually 180 to 150 ° C, preferably _80 to + 80 ° C, and the reaction time is usually 0.1 to 48 ° C. Hours, preferably 0.5 to 24 hours.
  • the compound represented by the formula (II) in the above reactions (A) and (B) is an intermediate compound useful for producing the compound of the present invention, and includes a novel compound. .
  • Compounds of formula (II) are capable of forming salts, including any agriculturally acceptable salts, for example, inorganic salts such as hydrochlorides, sulfates, and nitrates. Acid salts; organic acid salts such as acetic acid salts and methanesulfonate salts; alkaline metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as magnesium salts and calcium salts; dimethylammonium Quaternary ammonium salts such as triethylammonium, etc .;
  • the present invention embraces all of these individual Isomers and mixtures thereof. Further, the compound of the formula ( ⁇ ) has optical isomers, and the present invention includes all of these isomers and mixtures thereof.
  • the compounds of the formula (II) include those having pest control activity.
  • the compound of the formula (II) or a salt thereof can be produced, for example, according to the reaction [c] and a conventional method for producing a salt.
  • Reaction [C] is usually performed in the presence of a base and a solvent.
  • Examples of the base include alkali metal such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium methoxide and potassium tert-butoxide; and metal hydrogen such as potassium hydride and sodium hydride.
  • Organic compounds such as methyllithium, n-butyllithium, tert-butyllithium, and phenyllithium; carbonates such as potassium carbonate and sodium carbonate; heavy compounds such as potassium bicarbonate and sodium bicarbonate Carbonates; metal hydroxides such as lithium hydroxide and sodium hydroxide; Amines such as nomethylamine, dimethylamine, and triethylamine; one or more amines are appropriately selected from pyridines, pyridines such as 4-dimethylaminopyridine, and the like.
  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene; dioxane, tetrahydrofuran, and getyl ether.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • dioxane dioxane
  • tetrahydrofuran tetrahydrofuran
  • Ethers alcohols such as methanol, ethanol, propanol, and tert-butanol; cyclic or cyclic such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane
  • Acyclic aliphatic hydrocarbons esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane, N, N-dimethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, pyridine
  • Polar aprotic solvents such as acetone; Ketones such as ketones; Monomechiruamin, dimethylcarbamoyl Ruamin, amines such as Toryechiruamin; and one or more water is needed selection.
  • the reaction temperature of the reaction (C) is usually -80 to 10: I 50 ° C, desirably _ 50 to 120 ° C, and the reaction time is usually 0.1 to 48 hours, Preferably, it is 0.5 to 24 hours.
  • the reaction [C] when Z is a halogen, after reacting the formula (VII) with the formula (VIII), a hydrolysis reaction is carried out if necessary. In order to improve the yield of the target compound of formula (II), it is desirable to carry out this hydrolysis reaction.
  • the compound represented by the formula (VII) in the reaction [C] can be produced by the method described in WO97 / 40009, particularly, pages 85 to 86, or a method analogous thereto.
  • the compound of the present invention is useful as an active ingredient of a pesticide.
  • pesticides such as insecticides, acaricides, nematicides, soil pesticides, fungicides, and pesticides in water.
  • Desirable embodiments of the pesticidal composition containing the compound of the present invention are described below.
  • pesticides such as insecticides, acaricides, nematicides, soil pesticides, and fungicides.
  • the pest control agent containing the compound of the present invention is useful as an insecticide, acaricide, nematocide, or soil insecticide (hereinafter abbreviated as a pesticide).
  • Namihada two, Nisenamihada two, Kanzahada two Plant parasitic mites such as Citrus red mite, Apple tick mites, Cyanophoridae, Citrus saccharidum, Nedani, etc .; Animal parasitic mites such as ticks; Aphid such as peach aphid, Petra aphid, Konaga, Spiny beetles, Lotus leafworms, Codling moths, Ball worms, Tobacco bad worms, Gypsy moths, Konomeiga, Chinokokaku monmonaki, Colorado potato beetle, Scotch beetle, Bolui building, Scarabaeidae, Scarabaeidae, Scarabaeidae, Codworm , Grasshoppers, flies, Agricultural pests such as caterpillars, tamanayaga, power brallaga, ari, etc .; such as root-knotweeds, cysts-census, neg
  • Plant parasitic nematodes Plant parasitic nematodes; gastropods, such as slugs and scabies; soil pests, such as duckweeds and scabies; sanitary pests, such as gadani, cockroaches, gadfly, acaie Storing pests such as Bakuga, Azukizombushi, Kokunusutomodoki, Tenebrionidae, etc .; Clothing, house pests such as Iga, Himechabushibushi, Termites, etc .; Species; other fleas, lice, It is effective for controlling flies.
  • pesticides containing the compounds of the present invention can be used to control plant parasitic mites, animal parasitic mites, agricultural pests, sanitary pests, clothing, house pests, indoor dust mites, etc. Especially effective.
  • the pesticides containing the compound of the present invention are also effective for controlling various insect pests which are resistant to drugs such as organophosphorus agents, carbamate agents and synthetic pyrethroid agents.
  • the compound of the present invention since the compound of the present invention has excellent systemic translocation, by treating a soil with a pesticide containing the compound of the present invention, soil harmful insects, mites, nematodes, abdomen At the same time as controlling insects and isopods, pests in the foliage can be controlled.
  • the force is useful as fungicides, For example rice blast, sheath blight, Gomaha blight;? Wheat powdery mildew, scab, Rust, snow rot, naked smut, eye spot, leaf blight, wilt; citrus black spot, scab; apple moss Nilia disease, powdery mildew, spot leaf spot, scab; pear scab, black scab; peach scab, scab, phomopsis rot; grape scab, scab, powdery mildew, Downy mildew; Oyster anthracnose, deciduous disease; Persimmon anthracnose, powdery mildew, vine blight, Downy mildew; Tomato ring spot, leaf mold, plague; Brassica vegetable black It is effective for controlling diseases such as spot blight; potato summer blight; blight; strawberry powdery mildew; gray mold and sclerotium
  • pesticidal agent containing the compound of the present invention include the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, various diseases, various soil diseases, and the like. And pest control agents for agricultural and horticultural use that comprehensively control harmful substances.
  • Pest control agents such as pesticides and fungicides containing the compound of the present invention are usually mixed with the compound and various agricultural auxiliaries to prepare powders, granules, water dispersible granules, wettable powders, aqueous solutions. Forces used in the form of suspensions, oily suspensions, aqueous solvents, emulsions, pastes, aerosols, micro-sprays, etc. s', as long as they meet the purpose of the present invention, It can be in any formulation form used in the art.
  • Auxiliaries used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white wool, kaolin, bentonite, mixtures of kaolinite and sericite, clay, sodium carbonate, baking soda, sodium sulfate, zeolite, starch, etc.
  • Solid carrier water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, benzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N — Solvents such as dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates Salt, alkylaryl sulfate, a Kildiglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disul
  • auxiliaries such as a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a safener, and a fungicide can be used.
  • the compounding ratio of the compound of the present invention and various auxiliaries is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In the actual use of these preparations, they can be used as they are, or diluted to a predetermined concentration with a diluent such as water, and can be used by adding various spreading agents as necessary.
  • the application of pesticides such as pesticides and fungicides containing the compound of the present invention cannot be specified unconditionally due to differences in meteorological conditions, formulation, application time, place of application, types and occurrence of pests, etc.
  • the active ingredient concentration is generally 0.05 to 800,000 ppm, desirably 0.5 to 5000 000 ppm, and the application rate per unit area is 0.05 to 10,000 g of the compound of the present invention per hectare. However, it is preferably 1 to 5000 g.
  • the application of the pesticide, which is a desirable embodiment of the pesticide containing the compound of the present invention is the same as described above.
  • the active ingredient concentration of 0.1 to 500,000 ppm preferably 1 to 100,000 ppm
  • the amount of application per unit area is based on the present invention per hectare.
  • the compound is 0.1 to 10000 g, preferably 10 to 1000 g, and the application of the bactericide cannot be unconditionally specified due to the difference in various conditions as described above.
  • 0.1 to 500,000 ppm is desirable. Is carried out at an effective component concentration of from l to 100,000 ppm, and the application rate per unit area is from 0.1 to 10,000 g, preferably from 10 to 1,000 g, of the compound of the present invention per hectare.
  • the application of the pesticidal composition for agricultural and horticultural use which is another desirable embodiment of the pesticidal composition containing the compound of the present invention, is performed according to the above-mentioned application of the pesticide and the fungicide.
  • the present invention also includes a method for controlling harmful pests by such an application method.
  • pesticides such as insecticides and fungicides containing the compound of the present invention, or application of dilutions thereof, are usually applied by the general application method, that is, spraying (for example, spraying, spraying, Misting, atomizing, granulation, surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.), immersion bait etc.
  • spraying for example, spraying, spraying, Misting, atomizing, granulation, surface application, etc.
  • soil application mixtureing, irrigation, etc.
  • surface application application, dressing, coating, etc.
  • immersion bait etc.
  • ultra-low volume spray method In this method, it is possible to contain 100% of the active ingredient.
  • pesticides such as pesticides and fungicides containing the compound of the present invention can be mixed with or used in combination with other pesticides, fertilizers, and safeners. , May show action.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antivirals, attractants, antibiotics, plant hormones, plant growth regulators, etc.
  • a mixed pest control composition in which the compound of the present invention and one or more of the active ingredient compounds of other pesticides are mixed or used in combination, the application range, timing of chemical treatment, control activity, etc. in a favorable direction. that force is? possible to improve.
  • the compound of the present invention and the active ingredient compound of another pesticide may be prepared separately and mixed at the time of spraying, or both may be prepared together and used.
  • the present invention also includes such a mixed pest control composition. It is.
  • the mixing ratio of the compound of the present invention to the active ingredient compound of another pesticide cannot be specified unconditionally due to differences in weather conditions, formulation, application time, place of application, types of pests and occurrence, but generally 1: 1. 300 to 300: 1, preferably 1: 100 to 00: 1.
  • the appropriate amount of application is 0.1 to 5000 g, preferably 10 to 3000 g, as the total amount of the active ingredient compound per hectare.
  • the present invention also includes a method for controlling pests and pests by a method for applying such a mixed pest control composition.
  • Examples of the pesticides, acaricides, nematicides or soil pesticides in the above-mentioned other pesticides, ie, active ingredient compounds of the pesticides include, for example, profenophos (P rofenofos) ⁇ dichlorvos (D ichiorvos), fenamiphos (Fen am iphos), funitrothion (F enitrothion), EPN, diazinone (D iazin 0 n), chlorpyrifos methyl (Ch iorpyrifos- me thyl), acephate (Ac ephate), Organophosphate compounds such as Prothiofos, Phosthiazate, Phosphocarb, etc .;
  • Carbaryl (Carbary 1), Provoxur (Propoxur), Aldicarb (A1 dicarb), Carbofuran (Carbofuran), Thiodicarb (Thiodicarb), Methomil (Meth omyl), Oxamil ( ⁇ xamy1), Echioffencarp Carbamate compounds such as (E thiofencarb), Pirimicarb, and Fenobubucarb;
  • Neraist toxin derivatives such as cartap (Cartap), thiocyclam (Thiocyc1am);
  • Organic chlorinated compounds such as dicophor (Dic0f01) and tetradiphone (Tetradifon);
  • Organometallic compounds such as fenbutatin oxide (Fenbutatatin Oxide);
  • Benzoyl perylene compounds such as difluvenzuron (Diflubenzenzuron), chlorfluazuron (Ch1orrfluazazuron), tefluvenzuron (Teflubenzuron), and nonolulone (Novarulon);
  • Juvenile hormone-like compounds such as methoprene (Methaoprene);
  • Pyridazinone compounds such as pyrigben (Pyridaben);
  • fenpyroximate Fenpyroximate
  • Fipronil Fipronyl
  • Tebufenpyrad tebufenpyrad
  • Neonicotinoids such as imidacloprid (I midac 1 oprid) ⁇ nitenpyram, acetamiprid, diacloden (Diac 1 ode n ), thiacloprid (T hiac 1 oprid);
  • Hydrazine-based compounds such as tebufenozide (Tebufenozid), methoxfenozide (Methoxyfenozid), and chromafenozide (Chromomafenozid);
  • AV ermectin avermectin
  • milbemycin milbe
  • Examples of the active ingredient compound of the fungicide (generic name; including some applications) in the other pesticides include, for example, mepanipyrim, pyrimesanil (Pyrimethani 1), and cyprodinil (Cyprodini 1).
  • Pyrimidinamine compounds Triadimefone (T riadimef 0 n), bitertanol (Bitertano 1), triflumizol (T riflum izole), etaconazole (E taconazo 1 e), propiconazol (P ropiconazo 1 e), Penconazo 1 (Penconazo 1 e), Flusilazol (Flusi 1 azo 1 e), Microbutanil (Myc 1 obutani 1), Cyproconazole (Cyproconazo 1 e), Terbuconazole (Terbuconazole) ), Hexaconazole (Hexaconazole), Furconazole (Furconazol e_c is Prochloraz (Pro azole compounds such as chlorconaz), metconazole (Metconazole), epoxyconazole (Epoxiconconazle1e, tetraconazole (Tetraconaz01e);
  • Quinoxaline-based compounds such as quinomethionate (Quinomethionate);
  • Dithiocarbamate compounds such as maneb (Maneb), zineb (Zineb), manzeb (Mancozeb), polycarbamate (Polycarbamate), and propineb (Propine);
  • Organochlorine compounds such as husalide (Fthalide), chlorothalonil (Chororothalon1), and quintozene (Quint0zene);
  • Benomyl (Benomyl), Thiophanate-Methyl, Carbendazim, 4-Chloro-2-cyano 1 _Dimethylsulfamoyl-1-5- (4-Methylphenyl) Imidazo-I Imidazole-based compounds such as Pyridinamine compounds such as fluazinam (F 1 uazin am);
  • Cyanoacetamide-based compounds such as cimoxanil (Cymo Xani 1); metalaxyl (Meta 1 a Xy 1), oxadixyl ( ⁇ xadixy 1), ofures (O furace), benalaxyl (Benalaxyl), and furalaxil ( Phenylamide-based compounds such as Fu ra 1 a X y 1) and Cyprofuram;
  • Sulfenic acid-based compounds such as diclofluoride (Dich10f1uanid); Copper-based compounds such as cupric hydroxide (Cuprichydroxide) and organic copper (OxineCopper);
  • Isoxazol-based compounds such as hydroxysoxazole (Hydroxyisoxazole);
  • Fosetylaluminum (Fostyyl_Al), turquophosmethyl (Tolcfos—Methy1), S-benzyl 0,0-diisopropyl phosphorothioate,
  • Organophosphorus compounds such as 0-ethyl S, S-diphenyl phosphorodithioate, aluminum ethylhydrido genphosphonate;
  • N-halogenothioalkyl compounds such as captan (Captan), captaphor (Captafo1), and phthalate (Fo1pet);
  • Dicarboxyimide compounds such as procymidone (Procymidone), iprodione (I prodione), and hinclozolin (Vinc10z01in); such as flutolanil (Flutolani1) and mepronil (Meproni1) Benzanilide compounds;
  • Piperazine compounds such as trifoline (Triffine);
  • Pyridine compounds such as pyrifenox (Pyrifenox);
  • Carbinol-based compounds such as fenarimol (Fenarimol) and furtriafluor (Fiutriafil);
  • Piberidine compounds such as fenpropidine; morpholine compounds such as fenpropimorph; Organotin compounds such as fentin hydroxide, fentin acetate, etc .;
  • Urea-based compounds such as Penciclone (Pencycuron);
  • Cinamic acid-based compounds such as dimethomorph (Dimethomol ph); felucca-based compounds such as jetfencalp (Diet fofencarb);
  • Cyanopyrroyl compounds such as fludioxonil (Fludioxoni1) and fenpiclonil (Fenpicloni1);
  • Methoxyacrylate-based compounds such as azoxis trobin (Az0Xystr0bin), kresoximmethyl (Kresosim—Methyl), metominophen (Metominofen);
  • Oxazolidinone compounds such as famoxadone; atraquinone compounds; crotonic acid compounds; antibiotics and other compounds such as isoprothiolane (Is0pr0thi01ane) and tricyclazole (Tricyclazole).
  • Pyroquilon Pyro qu ilon
  • Diclomedine Diclom ezine
  • Probenazole Probenazo 1 e
  • Quinoxyfen Quinoxyfen
  • Propamorocarb hydrochloride Prop amo carb Hy drochloride
  • Spiroxamine Sp irox am ine
  • pest control agents such as biofouling agents in water are described.
  • Underwater biofouling agents containing the compound of the present invention can be used for ships and underwater structures (for example, harbor facilities, buoys, pipelines, bridges, submarine bases, offshore oilfield drilling facilities, power plant headraces, stationary nets) Control of harmful water-borne organisms against marine water, etc., specifically, plants such as green algae and brown algae, animals such as fujibo, selbra, sea squirt, mussels, oysters, etc., and slime It is effective in preventing aquatic organisms such as various bacteria, molds, diatoms, etc. from adhering to the ship's bottom and underwater structures and preventing their propagation.
  • aquatic organisms such as various bacteria, molds, diatoms, etc.
  • the underwater organism-controlling agent containing the compound of the present invention provides an antifouling property and a slime resistance for a long period of time, and has an excellent effect of preventing harmful underwater organisms from adhering to ships and underwater structures and preventing their propagation. Demonstrate fruit.
  • the water-borne biocontrol agent containing the compound of the present invention is usually formulated as a coating composition, and may be used in the form of a force, and in some cases, in another dosage form (solution, emulsion, pellet, etc.). it can.
  • the paint vehicle used when formulating the compound of the present invention as a paint composition include resin vehicle s that are usually used, such as 'powers to be mentioned', for example, vinyl chloride resins, vinyl chloride-vinyl acetate copolymers, and the like.
  • Vinyl chloride-vinyl isobutyl ether copolymer chlorinated rubber resin, chlorinated polyethylene resin, chlorinated polypropylene resin, acrylic resin, styrene-butadiene resin, polyester resin, epoxy resin, phenolic resin, synthetic rubber, Silicone rubber, silicone resin, petroleum resin, oil and fat resin, rosin ester resin, rosin stone, rosin, etc.
  • an organotin of unsaturated mono- or dicarboxylic acid obtained by a condensation reaction of (meth) acrylic acid with an organotin compound such as bis (triptyltin) oxide or triphenyltinhydroxide.
  • An acrylyl copolymer resin composition containing a compound salt as a constituent unit, a resin containing a metal element such as copper, zinc, and tellurium in a side chain can also be used.
  • the compounding ratio is 0.1 to 60% by weight, preferably 1 to 40% by weight of the compound of the present invention. Prepared.
  • the coating composition containing the compound of the present invention can be prepared, for example, using a ball mill, a pebble mill, a roll mill, a sand glider mill, or the like according to a method well known in the field of paint production.
  • the coating composition can contain a plasticizer, a coloring pigment, an extender, an organic solvent, and the like, which are generally used in the art.
  • the coating composition containing the compound of the present invention can further contain other known inorganic or organic antifouling agents, if necessary.
  • antifouling agents include, for example, cuprous oxide, copper rhodanide, copper hydroxide, copper naphthenate, metallic copper, various tin compounds and dithiolrubamic acid derivatives such as tetramethylthiuram monosulfide, Tetramethylthiuram disulphide, bis-bis (dimethyldithiocarbamate) zinc, ethylene-bis (dithioflavin) zinc, ethylene-bis (dithiocarbamic acid) manganese, bis-dimethy Ludici talent rubamic acid) Copper.
  • the compound of the present invention is effective as an active ingredient of a pesticidal agent.
  • a pest control agent for agricultural and horticultural use containing the formula (I) or a salt thereof as an active ingredient, or a method for controlling pests in the agricultural and horticultural field using the compound.
  • a pesticide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling pests using the compound is a pesticide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling pests using the compound.
  • a nematicide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling nematodes using the compound is a nematicide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling nematodes using the compound.
  • a fungicide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling harmful bacteria using the compound is a fungicide containing the above formula (I) or a salt thereof as an active ingredient or a method for controlling harmful bacteria using the compound.
  • Table 1 shows typical examples of the compound of the present invention represented by the above formula (I). These compounds may be synthesized based on the above synthesis examples or the above-mentioned various methods for producing the compound of the present invention. I can do it.
  • Me methyl group
  • Et ethyl group
  • Pr propyl group
  • Bu butyl group
  • Pen pen Tyl group
  • He x hexyl group
  • P h phenyl group
  • t tertiary
  • Cy cyclo
  • benzyl (4-CI) represents a 4-cycloalkyl benzyl group. The same applies to other similar descriptions.
  • a drug solution prepared so that the concentration of the compound of the present invention was 800 ppm was prepared.
  • the leaves of only one primary leaf of the squid were transplanted into a cup (8 cm in diameter, 7 cm in height), and about 30 adult Nami-Nada two were inoculated. This was immersed in the above-mentioned chemical solution together with kidney leaves for about 10 seconds, air-dried, and left in a constant temperature room with lighting at 26 ° C.
  • viability was determined, and the adult kill ratio was determined by the following formula.
  • a drug solution prepared so that the concentration of the compound of the present invention was 800 ppm was prepared.
  • the leaves of only the primary leaves of kidney beans were transplanted into cups (8 cm in diameter and 7 cm in height), inoculated with adults of Nami-nada, and spawned for 24 hours to remove the adults. This was immersed in the above-mentioned chemical solution for about 10 seconds together with the ingen leaves, air-dried, and allowed to stand in a constant temperature room at 26 ° C with illumination.
  • the hatching state of the eggs was investigated, and the ovicidal rate was calculated by the following formula.
  • Rice seedlings are immersed in a chemical solution prepared so that the concentration of the compound of the present invention becomes 800 ppm for about 10 seconds, air-dried, and the roots are wrapped with moist absorbent cotton and placed in a test tube. Then, release 10 larvae of the larvae into this, cover the tube with gauze, and leave them in a constant temperature room with illumination at 26 ° C. When the survival of the insects is determined thereafter, the compound of the present invention shows an effective control effect.
  • Test Example 4 Peach aphid insecticidal test
  • a drug solution prepared so that the concentration of the compound of the present invention was 800 ppm was prepared. Pot with only one true leaf left (8 cm in diameter, 7 cm in height) After applying adhesive to the petiole of the planted eggplant, two to three adult females of the peach aphid wingless embryo were applied to the true leaf. Inoculated and bred. Two days after inoculation, the adults were removed and the number of larvae was counted. The eggplant leaves infested with the larvae were immersed in the above-mentioned chemical solution for about 10 seconds, air-dried, and allowed to stand in a constant temperature room at 26 ° C with illumination. On the 5th day after the treatment, viability was determined, and the mortality was calculated by the following formula. The withdrawn insects were considered dead.
  • Mortality (%) Number of dead insects / Number of treated larvae X 1 0 0
  • Tomato (cultivar: Bontelosa) is cultivated in a plastic bowl having a diameter of 7.5 cm.
  • 10 ml of a drug solution prepared so that the compound of the present invention becomes 500 ppm is sprayed using a spray gun.
  • the compound of the present invention shows an effective control effect.
  • Test Example 7 Wheat powdery mildew prevention effect test
  • a green alga (1 Selenastrum capricornutum or 2 Chlorella vulgaris) cultured in advance for 7 days is inoculated into an algal growth medium containing a drug solution prepared so that the concentration of the compound of the present invention is 100 ppm, and the temperature is kept constant at 20 ° C under illumination.
  • the compound of the present invention shows an effective control effect.
  • the above components are uniformly mixed to obtain a wettable powder.
  • Finely divided silica 25 parts by weight A mixture of the above components and the compound of the present invention are mixed in a weight ratio of 4: 1 to obtain a wettable powder.
  • Formulation Example 5
  • the above ingredients are uniformly mixed and pulverized.
  • (1) to (3) are uniformly mixed in advance, and diluted with an appropriate amount of acetone.
  • Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to make an ultra low volume formulation.
  • the above components are uniformly mixed and pulverized to obtain an aqueous suspension.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un nouveau composé qui est utile en tant que principe actif d'un agent de lutte contre les ravageurs. Le composés est un composé à base d'acryronitrile de formule (I), dans laquelle Q représente un phényle substitué ou non substitué ou analogue, X représente un naphtyle substitué ou non substitué ou -J, Y représente -C(=0)R1, -C(=S)R2 ou analogue, R1 représente un alkynyle substitué ou non substitué ou -SR3, R2 représente un alkyle substitué ou non substitué ou analogue, R3 représente un alkyle substitué ou non substitué ou analogue, et J représente un groupe hétérocyclique à 5 ou 6 chaînons présentant entre 1 et 4 atomes d'au moins un hétéroatome sélectionné dans le groupe formé de O, S et N à condition que X ne soit pas un groupe pyridyle et son sel.
PCT/JP1999/001047 1998-03-06 1999-03-04 Compose a base d'acryronitrile, son procede de production et agent de lutte contre les ravageurs renfermant ce compose WO1999044993A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU32748/99A AU3274899A (en) 1998-03-06 1999-03-04 Acryronitrile-based compound, method for producing the same and pest controllingagent comprising the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP10/73125 1998-03-06
JP7312598 1998-03-06
JP10/242516 1998-08-12
JP24251698 1998-08-12

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002088099A1 (fr) * 2001-04-27 2002-11-07 Nippon Soda Co.,Ltd. Composé thiazolylcinnamonitrile et agent pesticide
WO2003031421A1 (fr) * 2001-10-02 2003-04-17 Nippon Soda Co.,Ltd. Procede de preparation de derives d'ethene
US6987112B2 (en) 2000-11-02 2006-01-17 Nippon Soda Co., Ltd. Organic compound having cyano group and insecticides/miticides
WO2007100160A1 (fr) * 2006-03-03 2007-09-07 Nissan Chemical Industries, Ltd. Composes acrylonitrile
US7649104B2 (en) 2003-03-28 2010-01-19 Nissan Chemical Industries, Ltd. Process for producing acrylonitrile compound

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4988818A (en) * 1989-10-06 1991-01-29 Basf Aktiengesellschaft Synergistic triazole compounds
WO1997040009A1 (fr) * 1996-04-25 1997-10-30 Nissan Chemical Industries, Ltd. Derives ethyleniques et agents pesticides
JPH10158254A (ja) * 1996-10-04 1998-06-16 Ihara Chem Ind Co Ltd 水中付着生物防汚剤用樹脂
WO1998035935A1 (fr) * 1997-02-14 1998-08-20 Ishihara Sangyo Kaisha Ltd. Composes d'acrylonitrile, leur procede de production et les pesticides les contenant
WO1998042683A1 (fr) * 1997-03-21 1998-10-01 Nippon Soda Co., Ltd. Composes de triazole, leur procede de preparation, et insecticides et acaricides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4988818A (en) * 1989-10-06 1991-01-29 Basf Aktiengesellschaft Synergistic triazole compounds
WO1997040009A1 (fr) * 1996-04-25 1997-10-30 Nissan Chemical Industries, Ltd. Derives ethyleniques et agents pesticides
JPH10158254A (ja) * 1996-10-04 1998-06-16 Ihara Chem Ind Co Ltd 水中付着生物防汚剤用樹脂
WO1998035935A1 (fr) * 1997-02-14 1998-08-20 Ishihara Sangyo Kaisha Ltd. Composes d'acrylonitrile, leur procede de production et les pesticides les contenant
WO1998042683A1 (fr) * 1997-03-21 1998-10-01 Nippon Soda Co., Ltd. Composes de triazole, leur procede de preparation, et insecticides et acaricides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6987112B2 (en) 2000-11-02 2006-01-17 Nippon Soda Co., Ltd. Organic compound having cyano group and insecticides/miticides
WO2002088099A1 (fr) * 2001-04-27 2002-11-07 Nippon Soda Co.,Ltd. Composé thiazolylcinnamonitrile et agent pesticide
WO2003031421A1 (fr) * 2001-10-02 2003-04-17 Nippon Soda Co.,Ltd. Procede de preparation de derives d'ethene
US7649104B2 (en) 2003-03-28 2010-01-19 Nissan Chemical Industries, Ltd. Process for producing acrylonitrile compound
US8138368B2 (en) 2003-03-28 2012-03-20 Nissan Chemical Industries, Ltd. Process for producing acrylonitrile compound
US8324420B2 (en) 2003-03-28 2012-12-04 Nissan Chemical Industries, Ltd. Process for producing acrylonitrile compound
WO2007100160A1 (fr) * 2006-03-03 2007-09-07 Nissan Chemical Industries, Ltd. Composes acrylonitrile

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