WO1992000964A1 - Amine derivative - Google Patents

Amine derivative Download PDF

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Publication number
WO1992000964A1
WO1992000964A1 PCT/JP1991/000889 JP9100889W WO9200964A1 WO 1992000964 A1 WO1992000964 A1 WO 1992000964A1 JP 9100889 W JP9100889 W JP 9100889W WO 9200964 A1 WO9200964 A1 WO 9200964A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
general formula
alkenyl
alkynyl
Prior art date
Application number
PCT/JP1991/000889
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Haruhito Ohishi
Teruyuki Iihama
Keiichi Ishimitsu
Tomio Yamada
Renpei Hatano
Nobuo Takakusa
Jun Mitsui
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.
Publication of WO1992000964A1 publication Critical patent/WO1992000964A1/ja

Links

Classifications

    • 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
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel amine derivative, a process for producing the same, and an insecticide containing the derivative as an active ingredient.
  • An object of the present invention is to provide an agricultural chemical which can be synthesized industrially advantageously, has a certain effect and can be used safely.
  • the present invention has the general formula (I)
  • R is a 5- or 6-membered nitrogen-containing aromatic which may be substituted
  • X represents an optionally substituted alkylene group or an alkylidene group
  • R 2 represents hydrogen, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or Aryl group or one Y—R 3 , Y is ⁇ , S (0),, CO, C 02, 1 is 0, 1, 2,
  • R 3 is hydrogen, an alkyl group which may be substituted Alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or aryl.
  • A, B and D each independently represent an optionally substituted carbon atom, a heteroatom or a single bond
  • E represents C0
  • Q represents hydrogen, an optionally substituted alkyl group, alkenyl Group, 'alkynyl group or aryl group, nitro group, halogen atom or Z—R 4
  • Z is CO, C 02, S (0) m , m is 0, 1, 2, R 4 is substituted
  • Z is CO, C 02, S (0) m , m is 0, 1, 2, R 4 is substituted
  • the compound of the present invention is produced by any one of the following (1) to (4).
  • ⁇ is S (0) n R 5 , 0R 6 , Or n represents an enol hydroxyl group, n represents 0, 1, or 2, R 5 represents an optionally substituted C, to C 4 alkyl group or phenyl group, and R 6 represents an optionally substituted C, to (: Represents an alkyl group or a phenyl group or S 0 2 R 7 , and R 7 represents an optionally substituted C 4 to C 4 alkyl group or a phenyl group.
  • the compound represented by the formula [I] is The compound represented by the formula (m) is used without any solvent or in an inert solvent such as benzene, toluene, ethanol, DMF, DME, N-methylpyrrolidone, and acetic acid. In some cases, it can be produced by reacting min in the presence of a Lewis acid catalyst such as P-toluenesulfonic acid at room temperature to reflux temperature.
  • a Lewis acid catalyst such as P-toluenesulfonic acid at room temperature to reflux temperature.
  • the compound represented by the formula [I] can be obtained by adding the compound represented by the formula [IV] to a compound represented by the formula [IV] without solvent or in an inert solvent such as benzene, toluene, DMF, DME, THF, and N-methylpyrrolidone.
  • the amine represented by [ ⁇ ] can be produced by reacting in the presence of a base such as triethylamine, pyridine, DBU or the like at room temperature to reflux temperature.
  • Q is an optionally substituted alkyl group, alkenyl group, alkynyl or ⁇ reel, a nitro group, a halogen atom, C0R 4, C 02 R 4 and S (0) m R 4 (where m, R, have the same meanings as described above) can be produced from compounds of the formula [I] in which Q is a hydrogen atom.
  • a haptic agent such as Ride (DAST) or N-fluoropyridinium triflate
  • a compound in which Q is represented by C 0 R 4 , C 0 2 R 4 or S (0) m can be produced by acylating or sulfonating a compound in which Q is a hydrogen atom.
  • the reaction may be carried out without solvent or in an inert solvent such as benzene, toluene, THF, DME, chloroform, dichloromethane, ether, DMF, etc., and in some cases, sodium hydroxide, hydroxide, or potassium hydroxide. It proceeds smoothly from room temperature to reflux temperature in the presence of bases such as lyethylamine, pyridine, DBU, and alcoholate.
  • Acid chlorides such as acetyl chloride and benzoyl chloride, acid anhydrides such as acetic anhydride, trifluoroacetic anhydride, and benzoic anhydride, and methanesulfonyl are used as acylating agents and sulfonating agents.
  • examples thereof include sulfonic acid chlorides such as chloride and p-toluenesulfonyl chloride, and sulfonic anhydrides such as methanesulfonic anhydride and p-toluenesulfonic anhydride.
  • Compound R 2 is not hydrogen atom among the compounds represented by I]
  • Formula (I) can be prepared from compounds wherein R 2 is water atom among the compounds represented by the formula [I].
  • the reaction may be carried out neat or in an inert solvent such as benzene, toluene, chloroform, THF, ether, alcohol, acetonitrile, and in some cases, toluethylamine, pyridine, DBU, benzene.
  • an inert solvent such as benzene, toluene, chloroform, THF, ether, alcohol, acetonitrile, and in some cases, toluethylamine, pyridine, DBU, benzene.
  • the reaction is performed in the range of room temperature to reflux temperature in the presence of a base such as sodium carbonate and sodium hydride.
  • the compound represented by the formula [I] can be obtained by usual post-treatment.
  • the structure of the compound was determined by IR, NMR, and mass spectra.
  • Table 1 shows typical examples of the compounds of the present invention including the above Examples.
  • the compound of the present invention has high insecticidal activity against various insect pests such as insects, moths, aphids, black-tailed leafhoppers, and brown rice.
  • insect pests such as insects, moths, aphids, black-tailed leafhoppers, and brown rice.
  • many insect pests such as Japanese moth, pinworm, leafhopper, aphid, etc., have developed resistance to organic phosphorus agents and carbamates, causing a problem of insufficient efficacy of these agents. Effective drugs are also desired.
  • the compound of the present invention is an agent having an excellent insecticidal effect not only on susceptible strains but also on insect pests which are resistant to organic phosphorus and carbamate.
  • the insecticide of the present invention contains the compound represented by the general formula (I) as an active ingredient, and can be used as it is as a pure active ingredient compound. That is, they are used in the form of wettable powders, water solvents, powders, emulsions, granules, flowables and the like.
  • a vegetable powder such as soybean flour, flour, etc.
  • a fine mineral powder such as diatomaceous earth, apatite, gypsum, talc, bentonite, clay, etc.
  • sodium benzoate Organic and inorganic compounds such as urea, sodium sulfate and the like are used.
  • liquid dosage forms vegetable oils, mineral oils, petroleum fractions such as kerosene, kynlen and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, trichloride Use ethylene, methyl isobutyl ketone, water, etc. as the solvent.
  • a surfactant can be added if necessary to obtain a uniform and stable form. Obtained in this way
  • the wettable powders, emulsions, aqueous solutions, and flowables obtained are diluted with water to a predetermined concentration to form suspensions or emulsions, and the powders and granules are applied to plants as they are.
  • the compound of the present invention alone is sufficiently effective, but it can also be used in combination with various insecticides, acaricides and fungicides.
  • miticides and insecticides that can be used by mixing with the compound of the present invention are shown below.
  • Example 6 Emulsion Compound of the present invention 10 parts Alkylphenyl polyoxyethylene 5 parts Dimethylformamide 50 parts Kinylene 35 parts More than 50 parts are mixed and dissolved, diluted with water before use, and dispersed as an emulsion.
  • Example 7 wettable powder
  • Compound of the present invention 20 parts Higher alcohol sulfate 5 parts Diatomaceous earth 70 parts Silica '5 parts The above are mixed, pulverized into fine powder, diluted with water before use, and dispersed as a suspension.
  • the rice seedlings were immersed for 30 seconds in a drug solution diluted with water so as to have a compound concentration of 125 ppm in accordance with the formulation of the emulsion described in Example 6 of the drug. After air-drying, the treated seedlings were placed in a test tube and inoculated with 10 larvae of the third instar larvae of the strain resistant to organophosphorus and carbamate agents. They were covered with gauze and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%. Table 3 shows the results.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
PCT/JP1991/000889 1990-07-05 1991-07-02 Amine derivative WO1992000964A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2/176462 1990-07-05
JP17646290 1990-07-05
JP20923890 1990-08-09
JP2/209238 1990-08-09
JP5556291 1991-02-28
JP3/55562 1991-02-28

Publications (1)

Publication Number Publication Date
WO1992000964A1 true WO1992000964A1 (en) 1992-01-23

Family

ID=27295626

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1991/000889 WO1992000964A1 (en) 1990-07-05 1991-07-02 Amine derivative

Country Status (2)

Country Link
EP (1) EP0539588A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1992000964A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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US8334295B2 (en) 2007-06-29 2012-12-18 Korea Research Institute Of Chemical Technology Pyrimidine derivatives as HIV reverse transcriptase inhibitors
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EP0539588A1 (en) 1993-05-05

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