WO1994017048A1 - Derive d'oxadiazole - Google Patents

Derive d'oxadiazole Download PDF

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Publication number
WO1994017048A1
WO1994017048A1 PCT/JP1994/000070 JP9400070W WO9417048A1 WO 1994017048 A1 WO1994017048 A1 WO 1994017048A1 JP 9400070 W JP9400070 W JP 9400070W WO 9417048 A1 WO9417048 A1 WO 9417048A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
chloro
compound
fluorophenyl
Prior art date
Application number
PCT/JP1994/000070
Other languages
English (en)
Japanese (ja)
Inventor
Takashi Kishimoto
Kaoru Noda
Yasushi Shibata
Michihiko Matsuda
Renpei Hatano
Makio Yano
Takao Iwasa
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
Priority claimed from JP5112340A external-priority patent/JPH06298747A/ja
Application filed by Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Publication of WO1994017048A1 publication Critical patent/WO1994017048A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • A01N43/82—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 three ring hetero atoms

Definitions

  • the present invention relates to a novel oxadiazole derivative and an insecticide and acaricide. Background technology:
  • Japanese Patent Application Laid-Open Publication No. Hei 11-261381 (EP 2 735 344) describes compounds having acaricidal activity and related to the compound of the present invention. For example, the following compounds are described. is there.
  • An object of the present invention is to provide an insecticide and acaricide that is effective and can be used safely.
  • the present inventors have found that at least one ortho position of a phenyl group directly bonded to an oxaziazole ring is substituted with a fluorine atom, and On whether or para position with a t one butyl group at the meta position of Fuweniru group attached through a zone Ichiru ring carbon atoms - A_ C 4 H 8 1 (wherein, Alpha is an oxygen atom, a sulfur atom, A compound having an amino group, a methylene group, or a bond) has a high activity not only in the susceptible ticks but also in the resistant ticks, and furthermore has an excellent insecticidal activity.
  • the present invention has been completed.
  • the present invention provides a compound represented by the general formula (I):
  • X is a halogen atom, d-3 alkyl group, 3 alkoxy group, 3 alkyl Chiomoto, nitro group, C, - 3 alkyl optionally substituted amino group with a group, or C, -3 haloalkyl group;
  • r 1 and r 2 are each independently a hydrogen atom, a Ct- 3 alkyl group, a hydroxy group, a halogen atom, a thiocarbamoyl group optionally substituted with Ci- 3 alkyl,
  • R 2 is together in a go-between Okiso group, human Dorokishii Mi amino group, C - 3 alkoxy Lee Mi amino group, or a methylene group!;
  • Y 2, Y 3, Y 4 and Upsilon 5 each represents a hydrogen atom, ds alkyl group
  • Y 2 or Upsilon 4 is not t-butyl group
  • Y 3 is t _ butyl group, neo-pentyl group, t-butoxy group, or t- Puchiruchio group, shows the t-Puchiruami cyano group.
  • the production method of the compound of the present invention is as follows.
  • ha 1 represents a halogen
  • X, Y 1, Y 2 , Y 3, Y 4, Y 5, r!, R 2 are as defined above.
  • the reaction is carried out in an organic solvent, if necessary, in the presence of a base, for 1 hour to several 10 hours, from ⁇ 20 ° C. to the boiling point of the solvent used.
  • a base for 1 hour to several 10 hours, from ⁇ 20 ° C. to the boiling point of the solvent used.
  • the solvent DMF, acetonitril, THF, benzene, chloroform, dioxane and the like can be used.
  • base pyridine, triethylamine, DBU, sodium hydride, sodium hydroxide, sodium carbonate and the like can be used.
  • X, ⁇ 2, ⁇ 3 , ⁇ 4, ⁇ 5,, r 2 are as defined above.
  • the reaction is carried out in an organic solvent from 50 ° C. to the boiling point of the solvent used, for 1 hour to several 10 hours.
  • DMF, toluene, xylene, dichlorobenzene and the like can be used as the solvent.
  • ha 1 represents a halogen
  • reaction 2 has the same meaning as described above.
  • the reaction is carried out in an organic solvent, if desired, in the presence of a base.
  • X, ⁇ 2, ⁇ 3 , ⁇ 4, ⁇ 5,, r 2 are as defined above.
  • the reaction is carried out in an organic solvent from 50 ° C. to the boiling point of the solvent used, for 1 hour to several 10 hours.
  • DMF, toluene, xylene, dichlorobenzene and the like can be used as the solvent.
  • the compound of the present invention depends on the type of the substituent, It can also be produced by appropriately selecting similar reactions. Wherein ha 1, QX,, Y 2 , Y 3, Y 4, Y 5, r! , r 2 have the same meaning as described above. a)
  • r 3 r 4 represents a lower alkyl group.
  • r 5 and r 6 each represent a d alkyl group.
  • r represents a C, -3 alkyl group, d alkylcarbonyl group, Ci-alkoxy group, or a thiocarbamoyl group which may be substituted with C alkyl.
  • r 8 and r 9 each represent an alkyl group; Shows oxygen, sulfur, and nitrogen atoms. e)
  • r is t representing a C i- 3 alkyl group
  • r 1 D represents a C alkyl group.
  • r H represents a C 3 alkyl group
  • r 12 is C!-,. Shows an alkyl group.
  • the target product can be obtained by performing ordinary post-treatment after the reaction.
  • reaction solution was poured into ice water, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and filtered, and then ethyl acetate was distilled off under reduced pressure.
  • the obtained residue was separated and purified using a silica gel column to obtain 1 g of the desired N- (4-t-butoxyphenylacetoxy) -2-chloro-opening-6-fluoro-benzamidine.
  • the obtained residue is separated and purified by a silica gel column, and the desired 5 — ( ⁇ -methylthio-14-acetoxybenzyl) _ 3 _ (2 _ 1-6-fluorofuryl) — 1, 2, 4 — 5.1 g of oxaziazole was obtained.
  • the compound of the present invention has high activity against ticks resistant to known acaricides and also has high activity against pests such as aphids.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, grain storage pests, clothing pests, house pests, and the like.
  • Lepidopteran pests for example, Hasmonyoto, Totoga, Tamanayaga, Aomushi, Tamanaginba, Konaga, Jyanokokakumonhamaki, Chiyamahamaki, Momomoshinguiga, Nashihime Shingui, Mikanhamoguriga, Chiyanohogaga, Machinaga Hemiptera pests, such as Kamiga moga, Kobnomimea, Yo-chi bitten corn borra, Amerika shirohitori, Sujimadarameiga, Heliotis spp., Helicobelpa spp., Aggrotis spp., Iga spp., Kodolinga spp.
  • Insect pests for example, house termites, sarcophagid termites, etc.
  • Lepidopteran pests for example, rodents, lice, pests, for example, rodents, ticks, for example, mites, for example, Namihadani, Nisenamihadani, Kanzahadani, Citrus spider Ngoha Mite, mikansabidanii, lingosavidinii, tyrannid mite, brevipalpas.
  • Tosentiyu Rice Shingaresenchu, Matsunozai Senyu, etc.
  • the compounds of the present invention excellent killing adults effect, refreshing in insect effect, larvicidal effect, also c shows the ovicidal effect, in recent years diamondback moth, ⁇ down force, Yokobai, organic Li emissions agent in aphid like many pests and mites, carbamate
  • the development of resistance to drugs and acaricides has led to a problem of insufficient efficacy of these drugs, and drugs that are effective against pests and mites of resistant strains are desired.
  • the compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests and mites of organic phosphorus agents, carbamate agents, pyrethroid agents, and acaricide-resistant strains.
  • the insecticide and acaricide of the present invention contains the compound represented by the formula [I] as an active ingredient, and can be used 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.
  • plant powders such as soybean flour and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, clay and other mineral powders, sodium benzoate, Organic and inorganic compounds such as urea and sodium sulfate are used.
  • liquid dosage forms vegetable oils, mineral oils, petroleum fractions such as kerosene, xylene and sorbent naphtha, sikglohexane, siquiloxaxanone, dimethylformamide, dimethylsulfoxide, trichloroethylene Use methyl isobutyl ketone, water, etc. as the solvent.
  • a surfactant can be added if necessary to obtain a uniform and stable form.
  • the wettable powders, emulsions, aqueous solutions and flowables obtained in this way are diluted to a certain concentration with water and used as suspensions or emulsions. Is done. It goes without saying that the compound of the present invention is effective alone, 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.
  • Example 26 Emulsion Compound of the present invention 10 parts Alkyl phenyl polyoxyethylene 5 parts
  • Example 28 The above mixture is mixed and pulverized into fine powder, diluted with water before use and dispersed as a suspension ( Example 28).
  • Example 26 10 days after germination, seedlings sown in three-size pots were inoculated with iridescent aphid adults. One day later, the adult was removed, and the drug was applied to the cucumber parasitized by the produced nymphs.
  • a drug solution diluted with water was sprayed so that the compound concentration was 31 ppm. They were placed in a constant temperature room with a temperature of 25 and a humidity of 65%, and the insecticidal rate was examined after 6 days. The results are shown in Table 3 below.
  • T e Number of dead eggs in the treatment area
  • T 1 Number of dead larvae in the treated area

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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne un composé présentant des effets insecticides et acaricides excellents, représenté par la formule générale [I], dans laquelle Q représente (a) ou (b); X représente halogène, alkyle C1-C3, alcoxy C1-C3, alkylthio C1-C3, nitro, amino facultativement substitué par alkyle C1-C3, ou haloalkyle C1-C3; r1 et r2 représentent chacun indépendamment hydrogène, alkyle C1-C3, hydroxy, halogène, thiocarbamoyle facultativement substitué par alkyle C1-C3, thiocarbamoyloxy facultativement substitué par alkyle C1-C3, alcoxycarbonyloxy C1-C3, alcoxy C1-C3, -S(O)nr3 (où n représente en nombre entier compris entre 0 et 2, et r3 représente alkyle C1-C3), amino facultativement substitué par alkyle C1-C3, ou alkylcarbonyloxy C1-C3, ou dans un autre mode de réalisation r1 et r2 peuvent être combinés afin de représenter oxo, hydroximino, méthylène ou alcoxy-imino C1-3; et Y1, Y2, Y3, Y4 ainsi que Y5 représentent chacun indépendamment hydrogène, alkyle C1-C6, alcoxy C1-C10, alkylthio C1-C6, halogène, amino facultativement substitué par alkyle C1-C3, ou hydroxy; à condition que lorsque soit Y2 soit Y4 ne représente pas t-butyle, alors Y3 représente t-butyle, néopentyle, t-butoxy, t-butylthio ou t-butylamino.
PCT/JP1994/000070 1993-01-21 1994-01-20 Derive d'oxadiazole WO1994017048A1 (fr)

Applications Claiming Priority (12)

Application Number Priority Date Filing Date Title
JP2491593 1993-01-21
JP5/24915 1993-01-21
JP5/27626 1993-01-22
JP2762693 1993-01-22
JP5112340A JPH06298747A (ja) 1993-04-15 1993-04-15 新規なオキサジアゾール誘導体、その製造法及び有害生物防除剤
JP5/112341 1993-04-15
JP11234193 1993-04-15
JP5/112340 1993-04-15
JP5/128336 1993-04-30
JP12833593 1993-04-30
JP5/128335 1993-04-30
JP12833693 1993-04-30

Publications (1)

Publication Number Publication Date
WO1994017048A1 true WO1994017048A1 (fr) 1994-08-04

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ID=27549217

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1994/000070 WO1994017048A1 (fr) 1993-01-21 1994-01-20 Derive d'oxadiazole

Country Status (1)

Country Link
WO (1) WO1994017048A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63165376A (ja) * 1986-12-27 1988-07-08 Nippon Soda Co Ltd オキサ（チア）ジアゾ−ル誘導体その製造方法及び殺ダニ剤
JPH01261381A (ja) * 1988-04-12 1989-10-18 Nippon Soda Co Ltd オキサ（チア）ジアゾール誘導体、その製造方法及び殺ダニ剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63165376A (ja) * 1986-12-27 1988-07-08 Nippon Soda Co Ltd オキサ（チア）ジアゾ−ル誘導体その製造方法及び殺ダニ剤
JPH01261381A (ja) * 1988-04-12 1989-10-18 Nippon Soda Co Ltd オキサ（チア）ジアゾール誘導体、その製造方法及び殺ダニ剤

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