WO2014172924A1 - Dérivé de quinoléine et son application - Google Patents

Dérivé de quinoléine et son application Download PDF

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Publication number
WO2014172924A1
WO2014172924A1 PCT/CN2013/075323 CN2013075323W WO2014172924A1 WO 2014172924 A1 WO2014172924 A1 WO 2014172924A1 CN 2013075323 W CN2013075323 W CN 2013075323W WO 2014172924 A1 WO2014172924 A1 WO 2014172924A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrogen atom
compound
quinoline derivative
weight
halogen atom
Prior art date
Application number
PCT/CN2013/075323
Other languages
English (en)
Chinese (zh)
Inventor
唐剑峰
王如军
吴雪
潘光明
刘杰
李文宏
Original Assignee
山东省联合农药工业有限公司
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 山东省联合农药工业有限公司 filed Critical 山东省联合农药工业有限公司
Publication of WO2014172924A1 publication Critical patent/WO2014172924A1/fr

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Classifications

    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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

Definitions

  • the invention belongs to the technical field of insecticides, and in particular relates to a quinoline derivative and its use.
  • insect species are difficult to control, and some insect species have significantly increased resistance.
  • the existing insecticides have greatly reduced the rate of pest control, and developed a new type of agriculture and garden with excellent insecticidal activity. Insecticides are an inevitable measure to solve the current low rate of pesticide control.
  • Quinoline is chemically active and can react with other substances.
  • the resulting quinoline derivative has a broad spectrum of insecticidal activity and high biological activity.
  • the object of the present invention is to provide a quinoline derivative and its use in view of the problems in the prior art mentioned above.
  • the present invention adopts the following technical scheme: a quinoline derivative having a structure as shown in Formula A
  • R 2 does not. Bu 4 base
  • R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a d- 4 a group, a d- 4 alkyl group optionally substituted by a halogen atom, a d- 4 alkoxy group, a d- 4 carbonyl group, wherein R 4 , R 5 does not indicate a hydrogen atom;
  • R 6 represents a hydrogen atom or a halogen atom.
  • R 4 and R 5 each independently represent a hydrogen atom optionally substituted by a halogen atom, and a d- 4 courtyard group, wherein R 4 and R 5 do not simultaneously represent a hydrogen atom;
  • R 6 represents a hydrogen atom or a halogen atom.
  • R 4 represents CH 3 ;
  • R 6 represents a hydrogen atom.
  • Table is not C 2 H 5 ;
  • R 6 represents a hydrogen atom.
  • the quinoline derivative of the invention has a pyridine ring and a quinoline ring structure, and is used for the insecticide with high systemicity and good plant permeability, and can quickly and effectively kill agricultural and garden pests and diseases, insecticidal spectrum. Wide, environmentally compatible.
  • a quinoline derivative of the present invention or an agriculturally and pharmaceutically acceptable acid addition salt thereof as an active ingredient of an insecticide inhibits respiratory metabolism of a pest by inhibiting electron transfer of mitochondria between pest cytochrome b and cl At the same time, it can also act on the acetylcholine enzyme receptor, interfere with the nervous system of the pest, and kill and control the target organism through contact and killing, and the killing rate can reach 100%.
  • a quinoline derivative of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof can be used for killing larvae and adults of Lepidoptera, Coleoptera, Homoptera, Orthoptera, and does not produce cross-resistance Sexually, it also has strong killing activity against pests that have developed resistance.
  • R 2 does not. Bu 4 base
  • R 3 does not. Bu 4 base
  • R 4, R. 5 each independently represent a hydrogen atom, a halogen atom, firing d- 4-yl, optionally substituted by a halogen atom d- 4 embankment, alkoxy, d- 4-ylcarbonyl hospital, wherein R 4, R 5 does not indicate a hydrogen atom at the same time;
  • R 4 and R 5 each independently represent a hydrogen atom optionally substituted by a halogen atom, and a d- 4 courtyard group, wherein R 4 and R 5 do not simultaneously represent a hydrogen atom;
  • R 4 represents CH 3 ;
  • R 6 represents a hydrogen atom.
  • Table is not C 2 H 5 ;
  • R 3 represents CH 3 ;
  • R 5 represents CH 3 ;
  • the insecticide may be combined as an active ingredient with an agriculturally acceptable carrier, and the active ingredient of the insecticide is present in an amount of from 0.5 to 90% by weight.
  • the dosage form of the insecticide may be a dry powder, a visible powder, an emulsifiable concentrate, a microemulsion, a paste, a granule, a solution, a suspending agent, and prepared according to a known method.
  • the agriculturally and garden-acceptable acid addition salts thereof may be hydrochlorides, phosphates, nitrate sulfates or acetates.
  • reaction product is the quinoline derivative of the structure of the invention having the structure shown in the formula ,, and the synthesis reaction ends; when R ⁇ COOR, the reaction product is the intermediate IV, and the synthesis reaction continues: 0: o
  • R 5 each independently represent a hydrogen atom, a halogen atom, alkyl with 4 optionally substituted by a halogen atom hospital group i,
  • R 6 represents a hydrogen atom or a halogen atom
  • R 7 does not. ⁇ 4 ⁇ ;
  • the solvent described in the step 1-5 may be an alcohol solvent or hydrazine, hydrazine-dimethylformamide; and the base used in the basic conditions described in the steps 1 and 2 may be an organic base or an inorganic base.
  • a quinoline derivative having the general formula of the present invention and its use, according to the specific compounds in the table, can have the following specific synthesis examples:
  • Elemental analysis is: C, 56.48; H, 3.16; F, 22.33; N, 5.49; 0, 12.54.
  • Solvent 7 parts by weight of dimethyl sulfoxide
  • Emulsifier 2 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 2, compound 5, trichlorfon;
  • Solvent 7 parts by weight of dimethyl sulfoxide
  • Emulsifier 2 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 7, compound 8, compound 10,
  • Solvent 7 parts by weight of dimethyl sulfoxide
  • Emulsifier 2 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 11, compound 12, compound 14, avermectin;
  • Solvent 7 parts by weight of dimethyl sulfoxide; Emulsifier: 2 parts by weight of decyl aryl polyglycol ether;
  • Active ingredient 1 part by weight of compound 16 hydrochloride, malathion;
  • Solvent 7 parts by weight of dimethyl sulfoxide
  • Emulsifier 2 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 17, compound 20, bifenthrin;
  • Emulsifier 0.5 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 22, compound 23, compound 24, imidacloprid;
  • Emulsifier 0.5 parts by weight of decyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 30, compound 31, imidacloprid;
  • Emulsifier 0.5 part by weight of t alkyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 33, compound 34, compound 35, butyl thiocarbamate;
  • Emulsifier 0.5 part by weight of t-mercaptoaryl polyglycol ether
  • Active ingredient 1 part by weight I: compound 40, compound 44, fenthion;
  • Emulsifier 0.5 parts by weight of alkyl aryl polyglycol ether
  • Active ingredient 1 part by weight of compound 46, compound 47, compound 48, chlorpyrifos;
  • Active ingredient 1 part by weight of compound 51, compound 52, compound 53, flubenzuron;
  • Active ingredient 1 part by weight of compound 60, chlorpyrifos;

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)

Abstract

La présente invention concerne un dérivé de quinoléine et l'une de ses applications. Le dérivé de quinoléine présente une structure illustrée par la formule générale A. Le dérivé de quinoléine ou l'un de ses sels d'addition acide de qualité agricole ou horticole peut être employé en tant que principe actif d'insecticides en agriculture et horticulture pour tuer les insectes des ordres Lepidoptera, Homoptera, Coleoptera et Orthoptera, ne génère pas de résistance croisée, et présente également une activité létale supérieure vis-à-vis des nuisibles présentant une résistance préexistante aux pesticides.
PCT/CN2013/075323 2013-04-22 2013-05-08 Dérivé de quinoléine et son application WO2014172924A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201310139969.2 2013-04-22
CN201310139969 2013-04-22

Publications (1)

Publication Number Publication Date
WO2014172924A1 true WO2014172924A1 (fr) 2014-10-30

Family

ID=48812677

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2013/075323 WO2014172924A1 (fr) 2013-04-22 2013-05-08 Dérivé de quinoléine et son application

Country Status (2)

Country Link
CN (1) CN103214461B (fr)
WO (1) WO2014172924A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103214461B (zh) * 2013-04-22 2015-05-27 山东省联合农药工业有限公司 一种喹啉衍生物及其用途
CN104744352B (zh) * 2013-12-25 2017-08-04 沈阳中化农药化工研发有限公司 一种制备4‑取代氧基苯酚类化合物的方法
CN109320452B (zh) * 2017-07-31 2019-10-18 东莞东阳光科研发有限公司 喹啉类衍生物及其制备方法和用途
CN110452167B (zh) * 2018-04-16 2020-08-21 东莞市东阳光农药研发有限公司 喹啉类衍生物及其制备方法和用途
EP3790864A4 (fr) * 2018-05-04 2021-12-15 Dongguan Hec Pesticides R&D Co., Ltd. Dérivés de quinoléine, leurs procédés de préparation et leurs utilisations
CN113603641B (zh) * 2021-10-08 2021-12-14 湖南速博生物技术有限公司 一种flometoquin的制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1688193A (zh) * 2002-10-11 2005-10-26 明治制果株式会社 用于防治寄生虫的混合组合物
CN1708225A (zh) * 2002-10-30 2005-12-14 明治制果株式会社 用于防治水稻病害的杀菌组合物
CN1993328A (zh) * 2004-08-04 2007-07-04 明治制果株式会社 喹啉衍生物以及含有其作为活性组分的杀虫剂
JP2008110953A (ja) * 2006-10-31 2008-05-15 Meiji Seika Kaisha Ltd キノリン誘導体およびそれを含んでなる農園芸用殺虫剤
CN103214461A (zh) * 2013-04-22 2013-07-24 山东省联合农药工业有限公司 一种喹啉衍生物及其用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0407192B1 (fr) * 1989-07-07 1997-03-05 Meiji Seika Kabushiki Kaisha Dérivés acyloxy-4-quinoléine et compositions insecticides et acaricides les contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1688193A (zh) * 2002-10-11 2005-10-26 明治制果株式会社 用于防治寄生虫的混合组合物
CN1708225A (zh) * 2002-10-30 2005-12-14 明治制果株式会社 用于防治水稻病害的杀菌组合物
CN1993328A (zh) * 2004-08-04 2007-07-04 明治制果株式会社 喹啉衍生物以及含有其作为活性组分的杀虫剂
JP2008110953A (ja) * 2006-10-31 2008-05-15 Meiji Seika Kaisha Ltd キノリン誘導体およびそれを含んでなる農園芸用殺虫剤
CN103214461A (zh) * 2013-04-22 2013-07-24 山东省联合农药工业有限公司 一种喹啉衍生物及其用途

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CN103214461B (zh) 2015-05-27
CN103214461A (zh) 2013-07-24

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