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WO1991001978A1 - Derives de triazine - Google Patents

Derives de triazine Download PDF

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Publication number
WO1991001978A1
WO1991001978A1 PCT/JP1990/000951 JP9000951W WO9101978A1 WO 1991001978 A1 WO1991001978 A1 WO 1991001978A1 JP 9000951 W JP9000951 W JP 9000951W WO 9101978 A1 WO9101978 A1 WO 9101978A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
alkenyl
hydrogen
alkynyl
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/JP1990/000951
Other languages
English (en)
Japanese (ja)
Inventor
Keiichi Ishimitsu
Junji Suzuki
Takashi Kishimoto
Haruhito Ohishi
Tomio Yamada
Renpei Hatano
Nobuo Takakusa
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
Publication of WO1991001978A1 publication Critical patent/WO1991001978A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic 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
    • C07D405/14—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 three or more hetero rings
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to a novel triazine derivative, a method for producing the same, and an insecticide having the derivative as an active ingredient.
  • Background technology :
  • insecticides for example, organophosphorus pesticides such as parathion and malathion, and carbamate pesticides such as kyarvalyl and mesomil. .
  • organophosphorus pesticides such as parathion and malathion
  • carbamate pesticides such as kyarvalyl and mesomil.
  • insecticides have played an extremely important role in improving agricultural production.However, in recent years, the use of some of these insecticides has been regulated due to problems such as residual and accumulated environmental pollution, and as a result of long-term use, they have become resistant. Some have produced pests. 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.
  • 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.
  • X represents an optionally substituted alkylene group, a heteroatom, or a single bond
  • R 2 and R 3 represent hydrogen, each an optionally substituted alkyl group, an alkenyl group, an alkynyl group, click Roarukiru group, consequent Roaruke two Le group signaling is Ariru group one Y - R 5,
  • R 5 is hydrogen, an alkyl group which may be substituted, an alkenyl group, an alkynyl group A cycloalkyl group, a cycloalkenyl group or an aryl group;
  • R 6 and R 7 are the same or different and each represents hydrogen, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl; Group or aryl group, w
  • R ⁇ is two collected by filtration group, Shiano group, one P (0 R 8) 2 ( W is 0 or S, R 8 is hydrogen, optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, Represents a cycloalkenyl group or an aryl group.), 1 (indicates 3 ⁇ 4—, Q is 0, S (0) m.
  • R 9 is hydrogen, optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, consequent Roarukeniru group or Ariru The group, R '.
  • R 11 are the same or different and each represents hydrogen, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group or an aryl group, or one T—R 12 , T is S (0) ⁇ , —CO— or 1 C 0 2— , ⁇ is 0, 1, 2, R 12 is hydrogen, an optionally substituted alkyl group, alkenyl group, alkyninole group , A cycloanolealkyl group, a cycloalkenyl group or an aryl group.
  • BEST MODE FOR CARRYING OUT THE INVENTION The production of the compound of the present invention is carried out as follows. NR 2 NH Z -HCHO
  • the compound represented by the general formula [I] is obtained by the Mannich reaction with the compound of the formula [ ⁇ ]. , R 2 N Hz, and HCH 0 can be obtained in good yield by heating at room temperature, or in some cases, in a solvent such as alcohols.
  • 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, MASS and the like.
  • Example 1 (Compound No. 95): 3 In a solvent mixture of methanol 20 and water 2, N—2—corurubidine-1 5—irmethyl N'—methyl N ”—cyanoguanidine 1.4 & methylamine (40) 1.5 g of formalin (37% aqueous solution) and 2.5 g of formalin (37% aqueous solution) were stirred and refluxed overnight. After the completion of the reflux reaction, the solvent was distilled off, and the obtained filamentous material was subjected to power column chromatography. 1- (2-Chlorviridine-1-5-dimethyl) 1-2-Cyanoimino 3,5-Dimethyl hexahydro 1,3,5—Triazine 1.2 g were obtained.
  • N- 2 Klozoreviline 1 5 —I-N-methylamine 12 in a mixture of methanol 10 ffl £ and water 2 fl fl £ 1.6 g, methylamine 0.7 g (40% aqueous solution) and 1.5 g of formalin (37% aqueous solution) were charged and reacted under stirring at 50'C for 3 hours.
  • the solvent Quantitatively by washing out, pouring, and washing with methanol 1 1 (2—Chlorubilidin 1—5—Irmethyl) 1—2 2 Troinomin 5—Methyl ⁇ Kisahi Draw 1, 3,
  • Table 1 shows representative examples of the compounds of the present invention, including the examples described above.
  • the compound of the present invention has high insecticidal activity against various insect pests such as insect beetles, moth moth, aphids, black leafhoppers, and brown insect power.
  • insect pests such as insect beetles, moth moth, aphids, black leafhoppers, and brown insect power.
  • many insect pests such as moth moth, pinworm, leafhopper-aphid, etc. have developed resistance to organic phosphorus agents and carbamates, resulting in a problem of insufficient efficacy of these agents, and A drug that is also effective is desired.
  • the compound of the present invention is a drug having an excellent insecticidal effect not only on susceptible strains but also on insect pests resistant to organic phosphorus and carbamate-resistant agents.
  • the insecticide of the present invention has a compound represented by the general formula [I] as an active ingredient, and can be used as it is as a pure product of the active ingredient compound. That is, they are used in the form of wettable powders, water solvents, powders, emulsions, granules, flowables and the like.
  • a solid agent when a solid agent is used, plant powders such as soybean flour and wheat flour, diatomaceous earth, apatite, stone cultivation, mineral powder such as talc, bentonite, clay, etc.
  • Organic and inorganic compounds such as sodium benzoate, urea and sodium sulfate are used.
  • liquid dosage forms vegetable oils, mineral oils, petroleum fractions such as ketocin, xylene and sorbent naphtha. Cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxy ', Trichlorethylene, Use solvent, water, etc. as solvent.
  • 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 prepare a suspension or an emulsion, and the powder and granules are sprayed on plants as they are. used.
  • the compound of the present invention is sufficiently effective alone, 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.
  • Organic and carbamate insecticides Phenthione, phenythrothione, diazinone, kurubiliphos, ESP, nomidione, phenetet.dimethate, formotion, marathon, dipterex, thiomethone , Phosmet, menazone, dichlorvos. Acefuit, EPBP, jarihole, methylparathion, oxidimethylmethyl, ethion, viraclohos.
  • Difluvenzuron, chlorfluazuron, triflumuron, tefluvenzuron, buprofezin, and machine oil are shown.
  • the agents and the like are not limited to these examples.
  • Compound of the present invention 10 parts Alkylphenylpolyoxyethylene 5 parts Dimethylformamide 50 parts Xylene 35 5 parts or more are mixed and dissolved, diluted with water and sprayed as an emulsion before use.
  • 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.
  • Example 2 Efficacy against black leafhopper A rice seedling 7 days after germination was immersed for 30 seconds in a chemical solution diluted with water to a compound concentration of 125 ppm according to the formulation of the emulsion described in Example 3 of the drug. did. After air-drying, the treated seedlings were placed in an examiner and inoculated with 10 third-instar larvae of the leafhopper leafhopper, a strain resistant to organophosphates and carbamates. They were covered with gauze, placed in a thermostatic chamber at a temperature of 25 and a humidity of 65%, and the insecticidal rate was examined after 5 days. Table 3 shows the results. Fig. 3

Landscapes

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

Abstract

L'invention se rapporte à des composés représentés par la formule générale (I) et à des sels de ces composés, ayant une activité insecticide puissante: où R1 représente un groupe hétérocyclique ou phényle éventuellement substitué; X représente un groupe alkylène éventuellement substitué, un hétéroatome ou une liaison simple; R2 et R3 représentent chacun un atome d'hydrogène, un groupe alkyle, alkényle, alkynyle, cycloalkyle, cycloalkényle ou aryle éventuellement substitué, -Y-R5, ou -NR6R7, où Y représente -O-, -S(O)n-, -CO-, ou -CO2-, n est égal à 0, à 1 ou à 2, R5 représente un atome d'hydrogène ou un groupe alkyle, alkényle, alkynyle, cycloalkyle, cycloalkényle, ou aryle éventuellement substitué, et R6 and R7 peuvent être identiques ou différents l'un de l'autre et représentent chacun un groupe similaire à R5; et R4 représente un nitro, un cyano, -P(=W)(OR8)2 (où W représente O ou S, et R8 représente un groupe similaire à R5), -Q-R9, ou -NR10R11, où Q représente un groupe similaire à Y, R9 représente un groupe similaire à R5, et R10 et R11 représentent des groupes similaires à R6 et R7, respectivement.
PCT/JP1990/000951 1989-07-28 1990-07-26 Derives de triazine Ceased WO1991001978A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP1/193937 1989-07-28
JP19393789 1989-07-28
JP23046389 1989-09-07
JP1/230463 1989-09-07

Publications (1)

Publication Number Publication Date
WO1991001978A1 true WO1991001978A1 (fr) 1991-02-21

Family

ID=26508193

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1990/000951 Ceased WO1991001978A1 (fr) 1989-07-28 1990-07-26 Derives de triazine

Country Status (2)

Country Link
AU (1) AU6044790A (fr)
WO (1) WO1991001978A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0483062A3 (en) * 1990-10-24 1992-10-28 Ciba-Geigy Ag Process for the preparation of nitroguanidine derivatives
WO1999009009A1 (fr) * 1997-08-20 1999-02-25 Novartis Ag Procede de production de composes organiques
WO2000040582A1 (fr) * 1999-01-08 2000-07-13 Bayer Aktiengesellschaft Derives de guanidine cycliques et leur utilisation comme pesticides
CN102372700A (zh) * 2010-04-02 2012-03-14 上海师范大学 1,5-二取代六氢三嗪化合物及制备方法和应用
CN101584337B (zh) * 2009-06-19 2013-03-06 上海师范大学 1,5-二取代六氢三嗪杀虫剂及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU628229B2 (en) * 1989-11-10 1992-09-10 Agro-Kanesho Co. Ltd. Hexahydrotriazine compounds and insecticides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0483062A3 (en) * 1990-10-24 1992-10-28 Ciba-Geigy Ag Process for the preparation of nitroguanidine derivatives
WO1999009009A1 (fr) * 1997-08-20 1999-02-25 Novartis Ag Procede de production de composes organiques
WO2000040582A1 (fr) * 1999-01-08 2000-07-13 Bayer Aktiengesellschaft Derives de guanidine cycliques et leur utilisation comme pesticides
AU763756B2 (en) * 1999-01-08 2003-07-31 Bayer Aktiengesellschaft Cyclic guanidine derivatives and their use as pesticides
US6683028B1 (en) 1999-01-08 2004-01-27 Bayer Aktiengesellschaft Cyclic guanidine derivatives and their use as pesticides
CN101584337B (zh) * 2009-06-19 2013-03-06 上海师范大学 1,5-二取代六氢三嗪杀虫剂及其制备方法
CN102372700A (zh) * 2010-04-02 2012-03-14 上海师范大学 1,5-二取代六氢三嗪化合物及制备方法和应用

Also Published As

Publication number Publication date
AU6044790A (en) 1991-03-11

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