WO1994011340A1 - Derive d'hydrazone - Google Patents

Derive d'hydrazone Download PDF

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Publication number
WO1994011340A1
WO1994011340A1 PCT/JP1993/001648 JP9301648W WO9411340A1 WO 1994011340 A1 WO1994011340 A1 WO 1994011340A1 JP 9301648 W JP9301648 W JP 9301648W WO 9411340 A1 WO9411340 A1 WO 9411340A1
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WIPO (PCT)
Prior art keywords
group
optionally substituted
substituted
alkyl group
hydrogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1993/001648
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English (en)
Japanese (ja)
Inventor
Takashi Kishimoto
Michihiko Matsuda
Renpei Hatano
Makio Yano
Jun Mitsui
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Soda Co Ltd
Original Assignee
Nippon Soda Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd
Priority to AU54337/94A priority Critical patent/AU5433794A/en
Publication of WO1994011340A1 publication Critical patent/WO1994011340A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/22—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups further bound to nitrogen atoms, e.g. hydrazidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/02—Compounds containing any of the groups, e.g. carbazates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/48—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • C—CHEMISTRY; METALLURGY
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Definitions

  • the non-invention relates to a novel hydrazone derivative and a pesticide.
  • Background technology :
  • organophosphorus pesticides such as parathion and malazone
  • carbamate pesticides such as kylarvalyl and mesomil.
  • organophosphorus pesticides such as parathion and malazone
  • carbamate pesticides such as kylarvalyl and mesomil.
  • These insecticides have played an extremely important role in improving agricultural production.However, in recent years, the use of some of these insecticides has been restricted due to problems such as residual and accumulated environmental pollution, and resistant pests have been identified as a result of long-term use. What happened is coming out. Therefore, there is a demand for the development of a new drug that has excellent insecticidal properties against various pests including these resistant pests and can be used safely.
  • EP 50011 is known as a compound similar to the compound of the present invention, but its acaricidal activity is not necessarily sufficient.
  • An object of the present invention is to provide an agricultural chemical that can be synthesized industrially advantageously, has a certain effect, and can be used safely. Disclosure of the invention:
  • the present invention has the general formula (I)
  • X is a halogen atom, an optionally substituted alkyl group, Alkoxy group, cycloalkyloxy group which may be substituted, alkylsulfonyloxy group which may be substituted, alkylthio group which may be substituted or alkylsulfonyl group which may be substituted.
  • R represents a hydrogen atom or an optionally substituted alkyl group
  • R 2 is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkylcarbonyl group, an optionally substituted alkyl group, an optionally substituted alkoxycarbonyl group, an optionally substituted alkoxycarbonyl group, A phenylcarboxy group which may be substituted or a phenylcarbamoyl group which may be substituted,
  • NR and R 2 may be taken together to form a 5- to 7-membered heterocyclic group containing N which may be substituted (provided that R and R 2 are further 1 to 2 Nitrogen or oxygen atoms),
  • R 3 represents a hydrogen atom or an optionally substituted alkyl group
  • R 4 represents an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted alkynyl group,
  • A represents a sulfur atom, an oxygen atom, an alkylene which may be substituted, alkylidene which may be substituted, carbonyl or N r 4 (where, r 4 is an alkyl group which may optionally be a hydrogen atom or a substitution. ),
  • n 0 or 1
  • Y represents an optionally substituted phenyl group or an optionally substituted pyridyl group.
  • examples of the group that substitutes alkyl or alkoxy include a halogen atom.
  • examples of the group for substituting fuunyl include a halogen atom, alkyl, haloalkyl, alkoxy, quino, loalkoxy, cycloalkyloxy and the like.
  • Examples of the group that substitutes the heterocyclic group include alkyl.
  • Examples of the group that substitutes a pyridyl group include a halogen atom.
  • the carbon number of alkyl and alkoxy is 1 to 6
  • the carbon number of cycloalkyl is 3 to 8
  • the carbon number of alkenyl and alkynyl is 2 to 6.
  • X, R,, R 2 , R 3 , R 4 , ⁇ , ⁇ , and ⁇ ⁇ have the same meanings as described above.
  • the reaction is carried out for 1 hour to several 10 hours in an organic solvent, if necessary, in the presence of an acid catalyst, at 0 ° C. to 200 ° C., and up to the boiling point of the solvent when a solvent is used.
  • the solvent include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, halogenated hydrocarbons such as carbon tetraform, carbon tetrachloride, and 1,2-dichloroethane, and tetrahydrofura.
  • ethers such as dioxane and dioxane.
  • R 5 and Re are the same or different and each represent a hydrogen atom, an optionally substituted alkyl group, and R 7 represents an optionally substituted alkyl group;
  • X, R 3 , A, n and Y have the same meaning as described above.
  • the reaction is carried out in an organic solvent, if desired, at 0 ° C. to 200 ° C. and, when a solvent is used, up to the boiling point of the solvent, for 1 hour to several 10 hours.
  • the solvent examples include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, and 1,2-dichloroethane, and tetrahydrocarbon.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • halogenated hydrocarbons such as chloroform, carbon tetrachloride, and 1,2-dichloroethane
  • Ethers such as drofuran and dioxane can be used.
  • the desired product can be obtained by performing ordinary post-treatment.
  • the structure of the compound of the present invention was determined from IR, NMR, MS and the like. BEST MODE FOR CARRYING OUT THE INVENTION
  • Example 1 4 'monochloro-2,2-dimethyl-2 -furanacetophenoxycarbonylhydrazone (Compound No. 4)
  • N C— N (CH 3 )
  • N C-NMe 2 mp
  • N C-thigh e 2
  • N CN e 2
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an insecticidal, nymphicidal, larvicidal and ovicidal action.
  • the following are typical examples.
  • Lepidopteran pests for example, Hasmonyoto, Totoga, Evening Managaga, Aomushi, Evening Managinaba, Konaga, Chino Kokakumonhamaki, Chiyamahamaki, Momoshinguiga, Nashihime Shinki, Mikanhamogiga, Chiya Nogamihoga Kameiga, Kobuno Meiga, Yo-Mouth Biancon Borra I, Ameri Kashiro Hitori, Sujimadarameiga, Heliotis, Helicoverpa, Agrotis, Iga, Kodlinga, Peta mimushi, etc.
  • Hemiptera pests such as peach aphids, evening aphids, Nisedai aphids, wheat bilee aphids, hosohelium stink bugs, stag beetles, stalks Coleoptera, Psyllides, Colorado beetle, Rice beetle, Coleoptera , Bean beetle, Burdock beetle, Diablotica, Tobacco beetle, Beetle bark beetle, Matsunomadara power beetle, Gomadara bee beetle, Agriotis genus, Nigyuyahoshten tou, Kokunusuto, Kota mizobushi, etc.
  • Pests of the eye e.g., fly, oak mouth flies, senchiniku flies, peri-mipa'e, mikanko mipa'e, corn flies, rice hammogliae, yellow flies, flies, flies, koga takaye, anetaishima power, shinahamadara Etc., insects of the order Thysanoptera, such as Thrips palmi Karny, Thrips japonicus, Hymenoptera, pests, such as C. elegans, C.
  • the compound of the present invention is an agent having an excellent insecticidal effect not only on susceptible strains, but also against pests of organic phosphorus agents, carbamates, pyrethroids, and resistant systems.
  • the pesticidal composition of the present invention contains a compound represented by the general formula [I] or a salt thereof as an active ingredient, and can be used as an active ingredient in a pure form.
  • the pesticide ie, wettable powder, water solvent, powder, emulsion, granule, flowable and the like.
  • solid additives such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, etc.
  • Organic and inorganic compounds such as fine powder, sodium benzoate, urea and sodium sulfate are used.
  • liquid dosage forms vegetable oils, mineral oils, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, trichlor
  • ethylene, methyl isobutyl ketone, water, etc. as solvents.
  • a surfactant can be added if necessary to obtain a uniform and stable form.
  • the wettable powder, emulsion, aqueous solution, and flowable thus obtained are diluted to a predetermined concentration with water to form a suspension or emulsion, and powders and granules are sprayed on plants as they are. Used in.
  • the compound of the present invention alone is sufficiently effective, but it can also be used in combination with various insecticides, acaricides, nematicides, fungicides and synergists.
  • insecticides and acaricides that can be used by mixing with the compound of the present invention are shown below.
  • Organophosphorus and carbamate insecticides Phenthion, Phenyltrothion, Diazinone, Chlorpyrifos, ESP'Midothion, Phentoate, Dimethoate, Formothion, Marathon, Trichlorfon, Thiometone, Phosmet, Dichlorvos , Acetate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicion, cyano hos, isoxathion, pyridaphthion, hosalon, methidathion, sulprophos, chlorfenbimphos, tetracloth Lorubinphos, Dimethylbinphos, Propaphos, Isofenphos, Ethylthiomethone, Profenofos, Pyraclofos, Monocrotophos, Azinphosmethyl, Aldicarb, Mesomil, Thiodicarp, Carbofuran, Carbosulfan, Py
  • Example 5 wettable powder
  • Example 7 granules
  • the compound was diluted with water so that the compound concentration became 125 ppm.
  • the corn leaves were immersed in the chemical solution for 30 seconds, air-dried, and then put into a petri dish containing five Atoto 3rd instar larvae.
  • the glass lid was put on the container, and the mixture was placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%. Two iterations. The results are shown in Table 2.
  • N CH-N (CH 3 3) 2 HC 1

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  • Life Sciences & Earth 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composé répondant à la formule générale (I), son sel, et agent pesticide. Dans la formule (I), X représente halogène, alkyle, alcoxy, cycloalkyloxy, alkylsufonyloxy, alkylthio ou alkylsulfonyle; R1 représente hydrogène ou alkyle; R2 représente hydrogène, alkyle, alkylcarbonyle, alkylcarbamoyle, alcoxycarbonyle, phénylcarbonyle ou phénylcarbamoyle; ou bien R1 et R2 peuvent s'associer pour former C(r1)Nr2r3, ou NR1R2 peut former un hétérocycle; R3 représente hydrogène ou alkyle; R4 représente alkyle, alcényle ou alcynyle; A représents S, O, alkylène, alkylidène, carbonyle ou Nr4; n vaut 0 ou 1; et Y représente phényle ou pyridyle.
PCT/JP1993/001648 1992-11-13 1993-11-11 Derive d'hydrazone Ceased WO1994011340A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54337/94A AU5433794A (en) 1992-11-13 1993-11-11 Hydrazone derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4328828A JPH06157444A (ja) 1992-11-13 1992-11-13 ヒドラゾン誘導体および有害生物防除剤
JP4/328828 1992-11-13

Publications (1)

Publication Number Publication Date
WO1994011340A1 true WO1994011340A1 (fr) 1994-05-26

Family

ID=18214541

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1993/001648 Ceased WO1994011340A1 (fr) 1992-11-13 1993-11-11 Derive d'hydrazone

Country Status (3)

Country Link
JP (1) JPH06157444A (fr)
AU (1) AU5433794A (fr)
WO (1) WO1994011340A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001001781A1 (fr) * 1999-07-05 2001-01-11 Basf Aktiengesellschaft Insecticides contre les fourmis et leur procede d'application
JP2001072516A (ja) * 1999-07-05 2001-03-21 Nippon Nohyaku Co Ltd 防蟻剤及びその使用方法
WO2002002515A1 (fr) * 2000-06-30 2002-01-10 Agro-Kanesho Co., Ltd. Derives hydrazone ou sels de ces derniers efficaces pour eliminer les animaux ou les insectes nuisibles
CN103641795A (zh) * 2013-04-18 2014-03-19 南开大学 一类含1,2,3-噻二唑的苯乙酮衍生物及其制备方法和用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56128746A (en) * 1980-03-13 1981-10-08 Ricoh Co Ltd New hydrazone compound and its preparation
JPS6393761A (ja) * 1986-07-17 1988-04-25 シエ−リング・アクチエンゲゼルシヤフト 置換ヒドラゾン、その製法およびこれを含有する有害生物防除剤
EP0500111A2 (fr) * 1991-02-22 1992-08-26 Ishihara Sangyo Kaisha, Ltd. Composés d'hydrazone, procédé pour leur préparation, intermédiaires utilisés et compositions pesticides les renfermant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56128746A (en) * 1980-03-13 1981-10-08 Ricoh Co Ltd New hydrazone compound and its preparation
JPS6393761A (ja) * 1986-07-17 1988-04-25 シエ−リング・アクチエンゲゼルシヤフト 置換ヒドラゾン、その製法およびこれを含有する有害生物防除剤
EP0500111A2 (fr) * 1991-02-22 1992-08-26 Ishihara Sangyo Kaisha, Ltd. Composés d'hydrazone, procédé pour leur préparation, intermédiaires utilisés et compositions pesticides les renfermant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001001781A1 (fr) * 1999-07-05 2001-01-11 Basf Aktiengesellschaft Insecticides contre les fourmis et leur procede d'application
JP2001072516A (ja) * 1999-07-05 2001-03-21 Nippon Nohyaku Co Ltd 防蟻剤及びその使用方法
WO2002002515A1 (fr) * 2000-06-30 2002-01-10 Agro-Kanesho Co., Ltd. Derives hydrazone ou sels de ces derniers efficaces pour eliminer les animaux ou les insectes nuisibles
CN103641795A (zh) * 2013-04-18 2014-03-19 南开大学 一类含1,2,3-噻二唑的苯乙酮衍生物及其制备方法和用途
CN103641795B (zh) * 2013-04-18 2016-03-02 南开大学 一类含1，2，3-噻二唑的苯乙酮衍生物及其制备方法和用途

Also Published As

Publication number Publication date
AU5433794A (en) 1994-06-08
JPH06157444A (ja) 1994-06-03

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