WO2017143892A1 - Acaricide d'ester d'acide sulfonique contenant des cycles spiro - Google Patents

Acaricide d'ester d'acide sulfonique contenant des cycles spiro Download PDF

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Publication number
WO2017143892A1
WO2017143892A1 PCT/CN2017/071622 CN2017071622W WO2017143892A1 WO 2017143892 A1 WO2017143892 A1 WO 2017143892A1 CN 2017071622 W CN2017071622 W CN 2017071622W WO 2017143892 A1 WO2017143892 A1 WO 2017143892A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
acaricide
acid ester
sulfonic acid
Prior art date
Application number
PCT/CN2017/071622
Other languages
English (en)
Chinese (zh)
Inventor
许良忠
吴华龙
王明慧
鞠光秀
徐姗姗
陈格新
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 WO2017143892A1 publication Critical patent/WO2017143892A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring

Definitions

  • the invention claims the priority of the Chinese invention patent application whose application date is February 25, 2016 and the application number is CN 201610102604.6.
  • the present invention relates to the field of acaricides in pesticides, and in particular to a sulfonate acaricide containing a spiro ring.
  • Plant pests are highly resistant to acaricides due to their strong fertility and short life cycle, which can severely reduce the yield of various crops.
  • acaricides such as scorpion, oxazolidine, acetylene, ethpyrazole, snail ester, etc. gradually decrease in effectiveness, and the duration of effect is gradually shortened.
  • Developing new acaricide varieties is the best way to solve the problem of resistance.
  • Patent CN 102060818 B discloses the preparation of a series of spirodecyl ester derivatives by reacting a compound of formula II with an alkyl chloroformate, some of which have good acaricidal activity.
  • Patent CN 103664850 B discloses an acaricide as shown in Formula III, which can be used alone or in combination with another biologically active compound to have a better control effect on agricultural pests.
  • the spirocyclic sulfonate acaricide and its acaricidal activity as described in the present invention have not been publicly reported at home and abroad.
  • the invention provides a sulfonate acaricide containing a spiro ring, and the structure is as shown in formula I:
  • the compound of formula I can be prepared by the following reaction:
  • the compound of formula II is reacted with butylsulfonyl chloride in the presence of an acid binding agent to form a compound of the invention (Formula I) in a solvent.
  • the acid binding agent is selected from the group consisting of triethylamine, pyridine, picoline, sodium carbonate (potassium), sodium hydrogencarbonate (potassium);
  • the solvent is selected from the group consisting of toluene, xylene, ethyl acetate, dichloromethane, chloroform, 1,2- Dichloroethane; butylsulfonyl chloride is added dropwise, the temperature is controlled from 0 ° C to 5 ° C, the purification method is recrystallization, and the solvent is selected from isopropanol.
  • the compound of the formula I is subjected to an indoor acaricidal egg activity test, and its activity is higher than that of the spironolactone at a concentration of 1 ⁇ g/mL and 0.1 ⁇ g/mL. Therefore, the present invention also includes the use of the compound of the formula I for controlling agricultural pests. .
  • the corrected mortality of the spirocyclic sulfonate-containing compound of the present invention against the eggs of T. cinnabarinus at the concentrations of 1 ⁇ g/mL and 0.1 ⁇ g/mL was 95% and 75%, respectively, higher than the control agent. 88% and 33% of snail esters (see Table 1).
  • the compound of the invention has simple preparation process and mild reaction condition, and is a new acaricide with good industrialization prospect.
  • the compound of the present invention can be used alone or in combination with other active substances in order to improve the comprehensive function of the product.
  • the invention also includes acaricidal compositions of the crop active component of the compound of formula I, which comprise a compound of formula I and an agriculturally acceptable carrier.
  • composition of the present invention can be used in the form of a preparation: the compound of the formula I is dissolved or dispersed in a carrier or a solvent as an active ingredient, and an appropriate amount of a surfactant is added to prepare a liquid, an emulsifiable concentrate, a microemulsion, an aqueous emulsion, a suspending agent. , dispersible oil suspension agent, etc.
  • Example 5 The activity of the acaricidal egg 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 ingredient, and immersing the leaves carrying the eggs of the cinnabar leaf mites (the eggs normally reared by the indoor standardized method) into the liquid, and gently shaking for 5 s. take out.

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 concerne un acaricide d'ester d'acide sulfonique contenant des cycles spiro, dont la structure est représentée en formule I. Le présent composé inhibe et élimine les acariens et les œufs d'acariens, et peut être utilisé en tant qu'acaricide pour prévenir l'apparition des acariens agricoles et lutter contre ces derniers.
PCT/CN2017/071622 2016-02-25 2017-01-19 Acaricide d'ester d'acide sulfonique contenant des cycles spiro WO2017143892A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610102604.6 2016-02-25
CN201610102604.6A CN105646421B (zh) 2016-02-25 2016-02-25 一种含螺环的磺酸酯类杀螨剂

Publications (1)

Publication Number Publication Date
WO2017143892A1 true WO2017143892A1 (fr) 2017-08-31

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2017/071622 WO2017143892A1 (fr) 2016-02-25 2017-01-19 Acaricide d'ester d'acide sulfonique contenant des cycles spiro

Country Status (2)

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CN (1) CN105646421B (fr)
WO (1) WO2017143892A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105646421B (zh) * 2016-02-25 2018-06-15 浙江博仕达作物科技有限公司 一种含螺环的磺酸酯类杀螨剂
CN107602515A (zh) * 2017-10-13 2018-01-19 南开大学 一类5a5b6c三环螺环内酯衍生物及其制备方法和用途

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5262383A (en) * 1991-07-16 1993-11-16 Bayer Ag 3-aryl-4-hydroxy- DELTA 3-dihydrofuranone and 3-aryl-4-hydroxy- DELTA 3-dihydrothiophenone derivatives and pesticidal use
CN1103642A (zh) * 1993-09-17 1995-06-14 拜尔公司 3-芳基-4-羟基-△3-二氢呋喃酮衍生物
CN102060818A (zh) * 2011-01-07 2011-05-18 青岛科技大学 一种新型螺螨酯类化合物及其制法与用途
CN102215684A (zh) * 2008-11-14 2011-10-12 拜耳作物科学公司 具有杀虫和杀螨特性的活性化合物复合物
CN103664850A (zh) * 2013-12-26 2014-03-26 青岛科技大学 一种螺螨磺酸酯化合物及其用途
CN105646421A (zh) * 2016-02-25 2016-06-08 浙江博仕达作物科技有限公司 一种含螺环的磺酸酯类杀螨剂

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5262383A (en) * 1991-07-16 1993-11-16 Bayer Ag 3-aryl-4-hydroxy- DELTA 3-dihydrofuranone and 3-aryl-4-hydroxy- DELTA 3-dihydrothiophenone derivatives and pesticidal use
CN1103642A (zh) * 1993-09-17 1995-06-14 拜尔公司 3-芳基-4-羟基-△3-二氢呋喃酮衍生物
CN102215684A (zh) * 2008-11-14 2011-10-12 拜耳作物科学公司 具有杀虫和杀螨特性的活性化合物复合物
CN102060818A (zh) * 2011-01-07 2011-05-18 青岛科技大学 一种新型螺螨酯类化合物及其制法与用途
CN103664850A (zh) * 2013-12-26 2014-03-26 青岛科技大学 一种螺螨磺酸酯化合物及其用途
CN105646421A (zh) * 2016-02-25 2016-06-08 浙江博仕达作物科技有限公司 一种含螺环的磺酸酯类杀螨剂

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KE , SHAOYONG ET AL.: "Spirodiclofen Analogues as Potential Lipid Biosynthesis Inhibitors: A Convenient Synthesis, Biological Evaluation, and Structure-Activity Relationship", BULL. KOREAN CHEM. SOC., vol. 31, no. 8, 31 December 2010 (2010-12-31), pages 2315 - 2321, XP055412036 *

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Publication number Publication date
CN105646421B (zh) 2018-06-15
CN105646421A (zh) 2016-06-08

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