WO2017148226A1 - Composé fluorobenzoxazole et son utilisation - Google Patents

Composé fluorobenzoxazole et son utilisation Download PDF

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Publication number
WO2017148226A1
WO2017148226A1 PCT/CN2017/071633 CN2017071633W WO2017148226A1 WO 2017148226 A1 WO2017148226 A1 WO 2017148226A1 CN 2017071633 W CN2017071633 W CN 2017071633W WO 2017148226 A1 WO2017148226 A1 WO 2017148226A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
fluorobenzoxazole
present
activity
Prior art date
Application number
PCT/CN2017/071633
Other languages
English (en)
Chinese (zh)
Inventor
许良忠
吴华龙
王明慧
李焕鹏
黄雪松
杨曦
Original Assignee
浙江博仕达作物科技有限公司
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 浙江博仕达作物科技有限公司 filed Critical 浙江博仕达作物科技有限公司
Publication of WO2017148226A1 publication Critical patent/WO2017148226A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Definitions

  • the present invention relates to the field of pesticide acaricides, and in particular to a fluorobenzoxazole compound and use thereof.
  • acaricides for controlling cockroaches such as acetylene, bromo oxime, avermectin, spironolactone, oxazolidine, hydrazine, and the like. Due to the long-term or frequent use of existing commercial acaricides, aphids have produced varying degrees of resistance and cross-resistance to existing insecticides. Therefore, the development of new or different activating agents with different mechanisms of action is an important means to control the resistance of cockroaches.
  • CN1038809A discloses an oxazole compound of the formula (I) which has strong insecticidal and acaricidal activity against pests and mites which are harmful to agriculture and horticulture, and which is almost phytotoxic to crops.
  • US5478855 discloses an oxazole compound of the formula III, which has excellent control effects on hawthorn leafhopper, citrus aphid, vegetable leafhopper, etc., and has the characteristics of super high efficiency, long-lasting effect, low toxicity and safety. .
  • the oxazole compound disclosed in the above patent has certain similarities with the compound of the present invention, but in the prior art, such as the fluorobenzoxazole compound of the present invention (Formula I) and its insecticidal and acaricidal activity No reports have been reported.
  • the compounds of formula I can be prepared by the following methods:
  • Ethylazole (Compound III) is a representative acaricide in oxazoline acaricides. It is a brand new uniquely synthesized compound developed by Sumitomo Chemical Co., Ltd., which is a new compound with leaf mites, leaves and leaves. Xenopus laevis, cinnabar leafhopper, citrus red spider, etc. have excellent control effect and excellent ovicidal activity. Not only the acaricide is ultra-efficient, but also has the characteristics of long-lasting effect and low pollution. The leader in the agent market, but due to the large number of frequent use of the acaricide in recent years, the mites have caused serious resistance to them, and the control effect and duration of action have been significantly reduced.
  • the present inventors have combined the years of research on the relationship between the efficacy of biologically active substances and the experience of bioresistant treatment to create a compound of the present invention (Formula I) by introducing a fluorine atom into the structure of the etoxazole.
  • acaricidal cough, scorpion egg
  • the compound of the present invention not only has an unexpected killing effect on the eggs (see Table 1), but also has good killing properties (see Table 2), and overcomes The disadvantage of acetoxime on the ineffectiveness of cockroach solves the shortcoming of the lack of quick-acting effect of acetoxime field control.
  • the compound of the present invention also has excellent insecticidal action (see Table 3).
  • the comprehensive control performance is significantly better than that of etoxazole.
  • the compound of the invention avoids the use of the highly toxic raw material diethyl sulfate in the synthesis process of oxazole, so that the production process is safer and more environmentally friendly; the introduction of fluorine atom is more beneficial to overcome or delay the generation of harmful drug resistance. Therefore, the compound of the present invention is a creative acaricide, and the commercialization thereof will be an ideal replacement product of an acaricide such as oxazole, and also an excellent insecticidal and acaricidal agent for the prevention and control of pests and cockroaches in China, and effectively promote the country. The development of the pesticide industry and the greening process of pesticides.
  • the present invention also encompasses acaricidal compositions of the compounds of formula I as active ingredients, which also include agriculturally or forestry acceptable carriers.
  • the compound of the present invention can be used alone or in combination with other active substances such as insecticides and acaricides in order to improve the comprehensive function of the product.
  • composition of the present invention can be administered in the form of a preparation, and the compound of the formula I is dissolved or dispersed in a carrier or a solvent as an active ingredient, and an appropriate surfactant is added to prepare an emulsifiable concentrate, an aqueous emulsion, a microemulsion, a suspending agent and the like.
  • the acaricidal egg activity was determined by the method of dipping and statistically correcting the mortality of the pest.
  • the specific process is: diluting the test agent to the required concentration according to the active ingredients, and injecting 50 mL of the drug solution into the culture dish under aseptic conditions, and then immersing them in the cinnabar eggs respectively (the eggs are normally reared according to the indoor standardized method)
  • the leaves were placed in a blank control with a plate containing 50 ml of sterilized water. Place the culture dish in a constant temperature incubator at 24 ⁇ 1 °C.
  • the mortality rate was investigated after 48 hours.
  • the activity data of the eggs and the mites are shown in Tables 1 and 2, respectively.
  • the compound I of the present invention has excellent acaricidal activity, and the activity of the compound I of the present invention is significantly superior to the known commercial acaricide (the compound of the formula III) at the same dose.
  • the compound I of the present invention has good killing properties, and overcomes the disadvantages of the compound of the formula III being ineffective.
  • Example 2 The activity of the compound of formula I to kill beet armyworm
  • the compound I of the present invention has excellent activity against Spodoptera exigua, and the activity of the compound I of the present invention is significantly superior to the known commercial acaricide (compound of the formula III) at the same concentration.

Landscapes

  • 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)
  • Agricultural Chemicals And Associated Chemicals (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 fluorobenzoxazole dont la structure est telle que représentée en formule I, et son utilisation. Le composé selon l'invention présente un excellent effet inhibiteur et destructeur des acariens et des œufs d'acariens, et peut être utilisé en tant qu'acaricide pour prévenir et traiter les acariens agricoles, et en même temps présente une excellente activité d'élimination des chenilles de l'asperge.
PCT/CN2017/071633 2016-03-01 2017-01-19 Composé fluorobenzoxazole et son utilisation WO2017148226A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610114395.7 2016-03-01
CN201610114395.7A CN105693648A (zh) 2016-03-01 2016-03-01 一种氟苯噁唑类化合物及其用途

Publications (1)

Publication Number Publication Date
WO2017148226A1 true WO2017148226A1 (fr) 2017-09-08

Family

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PCT/CN2017/071633 WO2017148226A1 (fr) 2016-03-01 2017-01-19 Composé fluorobenzoxazole et son utilisation

Country Status (2)

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CN (1) CN105693648A (fr)
WO (1) WO2017148226A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105693648A (zh) * 2016-03-01 2016-06-22 浙江博仕达作物科技有限公司 一种氟苯噁唑类化合物及其用途
CN107365279A (zh) * 2017-08-15 2017-11-21 上海开荣化工科技有限公司 乙螨唑的合成工艺
CN108424400A (zh) * 2018-06-09 2018-08-21 石家庄市绿丰化工有限公司 一种提高乙螨唑含量的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1038809A (zh) * 1988-06-09 1990-01-17 八洲化学工业株式会社 唑啉或噻唑啉衍生物和其制法
US5478855A (en) * 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
JPH0959115A (ja) * 1995-08-25 1997-03-04 Yashima Chem Ind Co Ltd 光安定性良好なる殺虫・殺ダニ組成物
CN105693648A (zh) * 2016-03-01 2016-06-22 浙江博仕达作物科技有限公司 一种氟苯噁唑类化合物及其用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002071827A2 (fr) * 2001-03-14 2002-09-19 Eli Lilly And Company Modulateurs des recepteurs x de retinoides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1038809A (zh) * 1988-06-09 1990-01-17 八洲化学工业株式会社 唑啉或噻唑啉衍生物和其制法
US5478855A (en) * 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
JPH0959115A (ja) * 1995-08-25 1997-03-04 Yashima Chem Ind Co Ltd 光安定性良好なる殺虫・殺ダニ組成物
CN105693648A (zh) * 2016-03-01 2016-06-22 浙江博仕达作物科技有限公司 一种氟苯噁唑类化合物及其用途

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