CN106632083A - Application of using pyrimidinyloxy-containing phenoxypropionic acid derivative as bactericide - Google Patents

Application of using pyrimidinyloxy-containing phenoxypropionic acid derivative as bactericide Download PDF

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Publication number
CN106632083A
CN106632083A CN201610878092.2A CN201610878092A CN106632083A CN 106632083 A CN106632083 A CN 106632083A CN 201610878092 A CN201610878092 A CN 201610878092A CN 106632083 A CN106632083 A CN 106632083A
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China
Prior art keywords
propionic acid
compound
phenoxy propionic
pyrimidinyloxy
pyrimidinyl oxy
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CN201610878092.2A
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Chinese (zh)
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CN106632083B (en
Inventor
黄治强
冯晨鹏
石军
吕丽娟
卜露霞
杨仁杰
王远宏
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Jinzhou Sihai biochemistry Co.,Ltd.
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Tianjin Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

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  • 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

The invention relates to a sterilization application of pyrimidinyloxy-containing phenoxypropionic acid derivative; the general formula is shown as (III). In formulas (I, II), R represents OH, benzyloxy, NH2, and substituted amido. Corresponding compound of the invention is possessed of sterilizing activity and can be used as agricultural bactericide.

Description

Containing 2-pyrimidinyl oxy phenoxy propionic acid analog derivative as antibacterial application
Technical field
The present invention relates to contain 2-pyrimidinyl oxy phenoxy propionic acid class compound as germicidal applications.
Background technology
Aryloxyphenoxypropanoates class (APP) compound is the high activity herbicide that a class prevents and kill off grassy weed.From 1975 Phenyl ring is gradually changed to heterocycle and annelated heterocycles by Nian Hou, people, and a series of high activity herbicide kinds are developed in succession. CN101613322A discloses aryloxyphenoxypropanoates analog derivative IA, IB and its their the weeding work that a class contains pyrimidine Property.CN103275029A discloses the chemical combination of a kind of aryloxyphenoxypropanoates analog derivative II with activity of weeding and its salt Thing.But up to the present, there is not the report as antibacterial application containing 2-pyrimidinyl oxy phenoxy propionic acid analog derivative.Cause This, this research containing 2-pyrimidinyl oxy phenoxy propionic acid analog derivative to being synthesized and the general sieve of biological activity finds that such compound can Using as antibacterial application.
The content of the invention
It is an object of the invention to provide a kind of new answering as antibacterial containing 2-pyrimidinyl oxy phenoxy propionic acid analog derivative With.There is presently no the report of the bactericidal activity related to such compound.
The change containing 2-pyrimidinyl oxy phenoxy propionic acid analog derivative with structure shown in following general structure (III) of the present invention Compound：
In formula (III), R represents OH, benzyloxy, NH2, substituted amido.
The analog derivative of phenoxy propionic acid containing 2-pyrimidinyl oxy (III) of the present invention can be prepared as follows：In alkali and By 4,6- dimethoxys -2- methanesulfonates yl pyrimidines (1) and (R) -2- (4- hydroxyphenoxies) propanoic acid in the presence of organic solvent (R) -2- [4- (4,6- dimethoxypyridin -2- epoxides) phenoxy group] ethyl propionate obtained and nucleophilic substitution in ethyl ester (2) there is (3), then there is saponification and obtain corresponding intermediate in intermediate 3 with organic solvent and water as mixed solvent in the presence of a base (R) -2- [4- (4,6- dimethoxypyridin -2- epoxides) phenoxy group] propanoic acid (4), finally by by intermediate 4 chloride is passed through React in the presence of a base with corresponding alcohol or (replacement) amine again afterwards and be converted into corresponding list of target compound (III).
Organic solvent is DMF, tetrahydrofuran, Isosorbide-5-Nitrae-dioxane, acetonitrile, dichloromethane, acetone.
Alkaline matter is in inorganic base sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium hydroxide, sodium carbonate or sodium hydride One or more or for organic base pyridine, triethylamine, 4-N, one or more in N- lutidines.
The phenoxy propionic acid containing 2-pyrimidinyl oxy and its derivant that the present invention is provided has certain bactericidal activity, can be used to prevent and treat One or more in cucumber downy mildew, wheat powdery mildew, rice blast and tomato late blight.
Compared with prior art, the beneficial effects are mainly as follows：The invention provides a kind of contain 2-pyrimidinyl oxy The application of phenoxy propionic acid and its derivant, such compound can be used for preventing and treating cucumber downy mildew, wheat powdery mildew, Oryza sativa L. rice blast One or more in disease and tomato late blight, such compound can be used directly, it is also possible to plus the load for agriculturally receiving Body is used, it is also possible to and other it is bactericide compounded use, can also provide basis for the research and development of novel pesticide.
Specific embodiment
Below again by specific embodiment to the present invention the above be described in further detail.But should not be by this The scope for being interpreted as above-mentioned theme of the invention is only limitted to below example, all technologies realized based on the above of the present invention Belong to the scope of the present invention.In following examples, fusing point is not calibrated.
Measure of the embodiment to cucumber downy mildew, tomato late blight, wheat powdery mildew and rice blast activity, mensuration program is such as Under：
Drug solution preparing：Weigh a certain amount of noval chemical compound to be dissolved in 2mL acetone, add the water containing 0.1% Tween 80, point It is not configured to the medicinal liquid 20mL of 400mg/L and 100mg/L.
Test host crop：Two leaf phase cucumber seedlings of greenhouse dixie cup Nutrition Soil culture, tomato seedling, Caulis et Folium Tritici aestivi and rice seedlings point Not successively as the test host plant of cucumber downy mildew, tomato late blight, wheat powdery mildew and rice blast.
Spraying treatment：Aerosol apparatus type is three-dimensional crops sprayer, and atomisation pressure is 1.5kg/cm2, spouting liquid is about 1000L/hm2, while processing above-mentioned test material, then natural air drying, is inoculated with pathogen after 24h.
Inoculation pathogen：Using inoculator by cucumber downy mildew, the spore of 1 × 105/mL of tomato late blight or rice blast Capsule suspension is inoculated in respectively successively cucumber leaves, tomato leaf, the rice leaf back side, and after moisturizing culture 24h, dislocation greenhouse is just Often management, investigates the bactericidal activity of compound after 4d.Separately Powdery Mildew spore is shaken off on wheat leaf blade, and in greenhouse after Continuous culture, investigates the bactericidal activity of compound after 7d.
As a result investigate：As a result investigation can write with reference to U.S.'s pathology of plants《A Manual of Assessment Keys for Plant Diseases》, represented with 100～0, the morbidity journey that disease-free and " 0 " level represents most serious is represented with " 100 " level Degree.
Table 1 is test result of the part of compounds to cucumber downy mildew, tomato late blight, wheat powdery mildew and rice blast.
Bactericidal activity test result (concentration of the partial target compound of table 1. to part pathogenic bacteria：mg/L)
aCucumber downy mildew (P.C.)
bTomato late blight (P.I.)
cWheat powdery mildew (B.G.)
dRice blast (P.G.).

Claims (3)

1. it is a kind of to contain 2-pyrimidinyl oxy phenoxy propionic acid class compound, it is characterised in that it has structure shown in below formula (III)：
In formula (III), R represents OH, benzyloxy, NH2, substituted amido.
2. it is according to claim 1 containing 2-pyrimidinyl oxy phenoxy propionic acid class compound, it is characterised in that to be preferably as follows structure Shown compound is protected.
3. the application containing 2-pyrimidinyl oxy phenoxy propionic acid class compound on pesticide described in right 1,2, it is characterised in that its tool There are one or more for suppressing cucumber downy mildew, tomato late blight, wheat powdery mildew and rice blast.
CN201610878092.2A 2016-09-28 2016-09-28 Contain application of the 2-pyrimidinyl oxy phenoxy propionic acid analog derivative as fungicide Active CN106632083B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248618A (en) * 1977-05-06 1981-02-03 Ici Australia Limited Derivatives of (pyrimidyloxy)phenoxy-alkanecarboxylic acid and herbicidal compositions thereof
JPH03287579A (en) * 1990-04-03 1991-12-18 Mitsubishi Petrochem Co Ltd Novel phenoxypropionic acid derivative and plant growth regulator with the same as active ingredient
CN101613322A (en) * 2009-07-28 2009-12-30 华中师范大学 One class contains the synthetic and weeding activity of the chiral aryloxy phenoxy propionic acid ester derivative of pyrimidine
CN104277034A (en) * 2013-07-02 2015-01-14 湖南化工研究院 N-(arylalkyloxy)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248618A (en) * 1977-05-06 1981-02-03 Ici Australia Limited Derivatives of (pyrimidyloxy)phenoxy-alkanecarboxylic acid and herbicidal compositions thereof
JPH03287579A (en) * 1990-04-03 1991-12-18 Mitsubishi Petrochem Co Ltd Novel phenoxypropionic acid derivative and plant growth regulator with the same as active ingredient
CN101613322A (en) * 2009-07-28 2009-12-30 华中师范大学 One class contains the synthetic and weeding activity of the chiral aryloxy phenoxy propionic acid ester derivative of pyrimidine
CN104277034A (en) * 2013-07-02 2015-01-14 湖南化工研究院 N-(arylalkyloxy)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof

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Effective date of registration: 20200601

Address after: Liu long Gou Xiang Da Qi Gou Cun, Yi County, Jinzhou City, Liaoning Province

Co-patentee after: Zhao Hongyang

Patentee after: Jinzhou Sihai biochemistry Co.,Ltd.

Address before: 300384 room 708, main building, Tianjin Agricultural University, 22 Jin Jing Road, Tianjin

Patentee before: Tianjin Agricultural University