CN110372622A - Phenyl acetanides containing chiral oxazoline and the purposes as disinfectant use in agriculture - Google Patents
Phenyl acetanides containing chiral oxazoline and the purposes as disinfectant use in agriculture Download PDFInfo
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- CN110372622A CN110372622A CN201810345936.6A CN201810345936A CN110372622A CN 110372622 A CN110372622 A CN 110372622A CN 201810345936 A CN201810345936 A CN 201810345936A CN 110372622 A CN110372622 A CN 110372622A
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- 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
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- 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
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- 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
- C07D263/14—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 with radicals substituted by oxygen atoms
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- 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
- C07D263/16—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The present invention relates to a kind of novel phenyl acetanides containing chiral oxazoline, and purposes of such compound as disinfectant use in agriculture, shown in the chemical structural formula of such compound such as following formula (I), the meaning of each group in formula is shown in that specification, the spatial configuration of such compound have a significant impact bacteriostatic activity；In logical formula (I) with substituent R1And R2The spatial configuration of the carbon atom of connection is R or S.
Description
Technical field
The present invention relates to a new class of phenyl acetanides containing chiral oxazoline and as the use of disinfectant use in agriculture
On the way；Application of such compound in fungal diseases of plants prevention and treatment is particularly related to, technical field of pesticide is belonged to.
Background technique
Chirality is a kind of essential attribute of nature, and the different enantiomters of chipal compounds are in bioactivity, toxicity
And all there is very big difference in degradation aspect.It is said from molecular level angle, the intracorporal target proteins of biology generally have specific
Space multistory configuration, it is a chiral Recognition process that pesticide molecule plays drug effect in vivo, ligand (pesticide molecule) and
The matching of receptor (target proteins) will be related to active size and safety.Chiral pesticide because of accurate identification with target,
Cost can be not only reduced to a certain extent, improves drug effect, also had to improve and be dived to non-target organism and environmental safety
Power meets the requirement of New pesticides discovery.Commercialization Chiral pesticide has been more than one third in pesticide market at present
(Lamberth, C., et al., Science, 2013,341,742-746.), and show the trend increased year by year.
Amides compound plays important role in pharmaceutical chemistry and field of pesticide chemistry, is that disinfectant use in agriculture is opened
Hair field classics and vigorous one kind.In recent years, a series of phenylacetamides fungicide and agriculture are developed based on mandelic acid
Medicine candidate compound, wherein representative fungicide mandipropamid (Eller, M., et al., WO2003042166.),
It has greater activity to inhibition spore germination, while to crop safety, to people, wild animal and Environmental security.It is excellent in structure
Introduced in change multiplicity heterocyclic units (Linker, K.H., et al., DE10360369.) or extend carbochain (Clemens,
L., et al., Pest Management Science.2007,63,57-62.), achieve good result.
This kind of fungicide and candidate compound typically contain multiple rotatable chemical bonds, are not involved with three-dimensional structure
Type and corresponding rigid backbone class compound；Also the phenyl acetanides containing chiral oxazoline unit, applicant are had no
Early period confirm chiral oxazoline have special property, and can be used as in new type bactericide is developed pharmacophore (Li,
S.；, etal.J.Agric.Food Chem.2016,64 (46), 8927-8934；Chinese invention patent application number:
201610762194.8)。
Present invention design has synthesized the phenyl acetanides containing chiral oxazoline, it is found that it has fungal diseases of plants
Strong inhibiting effect, chirality have a significant impact bacteriostatic activity, and in addition this kind of compound is readily synthesized, this wound to novel pesticide
It is formed with positive effect.
Summary of the invention
The technical problem to be solved in the present invention is to provide the preparation methods of the phenyl acetanides containing chiral oxazoline
And its application in prevention and treatment fungal diseases of plants.Phenyl acetanides performance of the present invention containing chiral oxazoline
Inhibit the effect of fungal disease, and the chirality (spatial configuration) of the hydroxyl of phenyl acetamide benzyl position and oxazoline ring well out
There is significant impact to bacteriostatic activity.
Chirality oxazoline class mandelic acidamide provided by the invention has structure shown in logical formula (I) as follows.
In logical formula (I) with substituent R1And R2The spatial configuration of the carbon atom of connection is R or S；
Ar indicates the phenyl that phenyl, 1-6 carbon oxyl that phenyl, halogen that phenyl, 1-6 carbon alkyl replace replace replace；
Substituent R1It respectively represents: hydrogen, hydroxyl, amino, carbonyl, 1-6 carbon alkoxy, benzyloxy, 1-6 carbon alkylamino, benzyl
Amino, fragrant oxygroup and fragrant amido；
Substituent R2It respectively represents: hydrogen, methyl, hydroxy methylene, hydrocarbyl carboxylic ester (1-6 carbon), 1-6 carbon alkyl, aromatic radical
With fragrant methylene.
The invention also includes the phenyl acetanides containing chiral oxazoline as shown in logical formula (I) on chemistry of pesticide
Acceptable salt.
Compound of the present invention can carry out chemical completion according to following synthetic route.
Method one, Steglich condensation reaction
Chirality oxazoline class intermediate B according to the present invention can be cheap and easy to get Gas chromatography be starting material
Synthesized that (Chinese invention patent application number: 201610762194.8), phenylacetic acid class compound directly can be bought or lead to
Cross derivative preparation.
The synthesis step of target compound C: by neighbour (4,5- dihydro -2- oxazoles-yl) Aniline intermediates B and phenylacetic acid class
It closes object A to be dissolved in anhydrous methylene chloride (can also be replaced with dichloroethanes), the condensing agent O- benzotriazole-of 1.1 times of amounts is added
The 4-dimethylaminopyridine (DMAP) of catalytic amount (10mol%) is then added, at room temperature in tetramethylurea hexafluorophosphate (HBTU)
It is stirred to react, saturated ammonium chloride solution quenching reaction, washes, precipitation, column chromatography for separation obtains object.
Method two, Passerini condensation reaction
Step 1, acetic anhydride (2 times of amounts) and formic acid (2.2 times of amounts) mixing are placed in 55 DEG C by the preparation of different nitrile compounds C
Lower reaction 2 hours；This mixed liquor is slowly added dropwise into the tetrahydrofuran solution of compound B (1 times of amount) at 0 DEG C, then gradually
25 DEG C are warming up to, (TLC detects reaction process to reaction 30min~1h, detects after extracting reaction solution a little neutralize, is extracted with organic solvent
Rear contact plate is taken to detect), after fully reacting, solvent is evaporated off, is dissolved in ethyl acetate, washes, after dry, solvent is evaporated off, obtains first
Amide raw product E is directly used in and reacts in next step.
Formamide crude product E (1 times of amount) is dissolved in anhydrous tetrahydro furan, three second are slowly added dropwise under condition of ice bath thereto
Amine (5 times of amounts)；Then under the conditions of 0 DEG C, the phosphorus oxychloride (POCl steamed again is slowly added dropwise thereto3, 1.5 times of amounts), TLC tracking
Monitoring reaction, after fully reacting use saturated ammonium chloride quenching reaction, be extracted with ethyl acetate completely (TLC monitoring inorganic phase show
Without object), after anhydrous sodium sulfate drying, column chromatography for separation obtains the different nitrile compounds C of target product.
Aldehyde or imine compound (1 times of amount) are weighed in clean and dry Schlenck reaction flask, in -78 DEG C and nitrogen
Under gas shielded, pyridine nitric oxide (0.1 times of amount) and silicon tetrachloride (1.1 times of amounts) are added thereto, is slowly added dropwise thereto
The dichloromethane solution (1.2 times of amounts) of isonitrile class intermediate C, at this temperature, magnetic agitation reaction, TLC tracking and monitoring, reaction
After completely, restore to room temperature, be slowly dropped in saturated sodium bicarbonate solution, TLC monitors reaction process, and reaction terminates
Afterwards, it is extracted with dichloromethane, it is dry with anhydrous sodium sulfate after merging, the phenyl acetamide classification containing chiral oxazoline is obtained after purification
Mark compound D or E.
The synthesis of phenyl acetanides provided by the present invention containing chiral oxazoline is cheap and easy to get with raw material, closes
At the few and easily operated feature of step.
Phenyl acetanides according to the present invention containing chiral oxazoline, preferably following compound:
First part:
Second part (substituent R2For substituent group shown in first part):
Part III (substituent R 2 be respectively substituent group shown in first part and second part with Ar):
Compound according to the present invention further includes the phenylacetamides chemical combination containing chiral oxazoline as shown in logical formula (I)
The salt that object can receive in Pesticide Science.
Phenyl acetanides provided by the present invention containing chiral oxazoline to the activity of plant pathogenic fungi, including
Rhizoctonia solani Kuhn (Rhizoctonia solani), rhizoctonia cerealis (Rhizoctonia cerealis), rape sclerotium
Germ (Sclerotinia scleotiorum), fusarium graminearum (Fusarium graminearum), gaeumannomyces graminis
(Gaeumanomyce graminis), botrytis cinerea (Botrytis cinerea), phytophthora infestans
(Phytophthora infestans), P. capsici (Phytophthora capsici), tomato early blight bacterium
(Alternaria solani), fusarium moniliforme (Fusarium fujikuroi), dry rot of potato bacterium (Fusarium
Sulphureum), cucumber anthracnose (Colletotrichum lagenarium), rice blast fungus
(Phyricularia cerealis)。
Detailed description of the invention
Protective effect of Fig. 1 compound D7 to grey mould fruit rot of strawberry
Specific embodiment
By following embodiments and biological activity determination experimental result, the present invention can be further illustrated and understood, but not
Mean the limitation present invention.
Embodiment one: the synthesis of compound D7
Step (1) weighs Gas chromatography (2.242g, 19mmol), (R) -2- amino-n-butyl alcohol (1.5mL, acetic anhydride
Zinc (0.366g, 2mmol) is placed in 150 DEG C of oil baths in dry seal pipe, thin-layer chromatography (TLC) tracking and monitoring react into
Journey, about 12h fully reacting add ethyl acetate EtOAc (15mL × 3) to extract, ethyl acetate phase water (10mL × 2), saturation chlorine
After changing sodium solution (10mL × 2) washing, anhydrous sodium sulfate is dry, evaporating solvent under reduced pressure, column chromatography for separation (petroleum ether/acetic acid second
Ester, 20: 1) obtaining yellow oil product B1, yield 56.4%.LC-MS (ESI+) m/z:Calcd.for [M+H:C11H14N2O]:
190.11, Found:191.21.
Step (2) weighs neighbour (4,5- dihydro -2- oxazolyl) Aniline intermediates B1 (1mmol, 0.190g), R-MA
(1mmol, 0.152g) and 4-dimethylaminopyridine DMAP (0.2mmol, 0.024g) are dissolved in 5mL bis- in 50mL eggplant type bottle
In chloromethanes DCM, under ice bath be added condensing agent O- benzotriazole-tetramethylurea hexafluorophosphate HBTU (1.3mmol,
0.493g), stirring at normal temperature, thin-layer chromatography (TLC) tracking and monitoring reaction process, about 6h post-processing.Add methylene chloride DCM (15mL
× 3) it extracts, after methylene chloride is mutually washed with water (10mL × 2), saturated sodium chloride solution (10mL × 2) respectively, anhydrous sodium sulfate
It dries, evaporating solvent under reduced pressure, (eluant, eluent: petrol ether/ethyl acetate=10: 1), obtaining compound D7, produces after silica gel column chromatography
Rate 51.3%.177.8~178.1 DEG C of fusing point.LC-MS (ESI+) m/z:Calcd.for [M+H:C19H20N2O3]: 325.15,
Found:325.18.
Embodiment two: the Antibacterial Activity of the phenyl acetanides containing chiral oxazoline
Inhibit mycelial growth rate method to carry out Antifungal Activity in Vitro evaluation using plate, chooses test strain in PDA plate
It is activated, including Rhizoctonia solani Kuhn (Rhizoctonia solani), rhizoctonia cerealis (Rhizoctonia
Cerealis), Sclerotinia sclerotiorum (Sclerotinia scleotiorum), fusarium graminearum (Fusarium
Graminearum), gaeumannomyces graminis (Gaeumanomyce graminis), botrytis cinerea (Botrytis
Cinerea), phytophthora infestans (Phytophthora infestans), P. capsici (Phytophthora
Capsici), tomato early blight bacterium (Alternaria solani), fusarium moniliforme (Fusarium fujikuroi), horse
Bell potato dry rot germ (Fusarium sulphureum), cucumber anthracnose (Colletotrichum lagenarium), water
Rice Pyricularia oryzae (Phyricularia cerealis).Compound is configured to the PDA drug containing tablet of graded series concentration, it will
Test strain is made 5mm diameter bacteria cake and is placed in drug containing culture dish center, the test strain of 25 DEG C of constant temperature incubations to blank control ware
It is long to close to culture dish edge when, the colony diameter of each drug containing tablet is measured with crossing method, it is raw to mycelia to calculate compound
Long inhibiting rate calculates the inhibiting rate of disease according to following formula:
The concentration of compound when inhibiting rate is 50%, i.e. EC are calculated using statistic software SPSS 20.050It is worth (mg/L), repeats
It is averaged for 3 times.With Boscalid (boscalid) for positive control, the bacteriostatic activity of synthesising target compound is measured.
Phenyl acetanides bacteriostatic activity of the table 1 containing chiral oxazoline
Embodiment three: the phenyl acetamide D7 containing chiral oxazoline tests the protective effect of grey mould fruit rot of strawberry
Compound D7 is directly dissolved in the water containing 0.05% Tween-80, it is standby to be made into the reagent agent that concentration is 50mg/L
With clear water control uses the pure water for containing 0.05% Tween-80.Using fruit needle point method, D7 is tested on living tissue to strawberry
The protective effect of gray mold.Strawberry fruit of uniform size is chosen, is uniformly applied to fruit surface, Boscalid with reagent agent
It is compareed as medicament.After for 24 hours, the fruit surface for smearing medicament is punctured, is inoculated with cultured Botrytis cinerea germ in advance
(Botrytis cinerea) bacteria cake, each fruit are inoculated with 1 bacteria cake, and it is straight that each processing measures scab in triplicate, after 2 days
Diameter.Control efficiency is calculated according to following equation:
Experimental result shows that compound D7 is 93.88% to the preventive effect of grey mould fruit rot of strawberry, is better than positive control Boscalid
Preventive effect 90.61%.
Protective effect of the 2 compound D7 of table to Botrytis cinerea germ
As can be seen from the table, this application involves the phenyl acetanides containing chiral oxazoline have to plant disease
Good inhibiting effect.The chirality of phenylacetic acid benzyl position hydroxyl is significant to activity influence.To Rhizoctonia solani Kuhn, grey mould fruit rot of strawberry
In bacterium Inhibition test, R type mandelic acid shows apparent activity advantage.And in the Inhibition test to Sclerotinia sclerotiorum, then
Opposite activity advantage is shown, the activity of S type mandelic acid is better than R type.The chiral of 4 bit substituent of oxazoline also deposits activity
Significantly affecting, when mandelic acid is when being configured as R, when 4 bit substituent of oxazoline is R type activity be generally better than or with S type phase
When.When mandelic acid is when being configured as S, then show opposite rule, when 4 bit substituents are S type activity be generally better than or with R type
Quite.To compound activity there are significant impact, Antifungal Activity in Vitro test result is shown the type of 4 bit substituent of oxazoline
It is following regular out: to the inhibitory effect iBu > Et > Me of Rhizoctonia solani Kuhn；To the inhibitory effect Ph > Et of Sclerotinia sclerotiorum
> Me；To the inhibitory effect Bn > Et > Ph > iPr of Botrytis cinerea germ.
When 4 are ethyl substituent on oxazoline ring, and are configured as R, good inhibition is shown to tested bacterial strain
Effect has certain broad spectrum activity, to concentration in the inhibition of Rhizoctonia solani Kuhn and Botrytis cinerea germ respectively down to 5.76 ±
0.17mg/L and 3.83 ± 0.12mg/L.In the Protection to grey mould fruit rot of strawberry, to Botrytis cinerea under the concentration of 50mg/L
The preventive effect of disease is 93.88%, is better than positive control Boscalid.Be expected to as a kind of novel fungicide candidate compound or
It is used directly as fungicide, it will be significant to New pesticides discovery.
Phenyl acetanides according to the present invention containing chiral oxazoline as disinfectant use in agriculture purposes
It is described by specific example, those skilled in the art can use for reference the content of present invention, appropriate feed change, process conditions
Etc. links realize corresponding other purposes, correlation changes all without departing from the contents of the present invention, all similar replacements and
Change is it will become apparent to those skilled in the art that be considered as being included within the scope of the present invention.
Claims (6)
1. acceptable salt on phenyl acetanides and its pesticide containing chiral oxazoline shown in logical formula (I) as follows,
Wherein,
In logical formula (I) with substituent R1And R2The spatial configuration of the carbon atom of connection is R or S；
Ar indicates the phenyl that phenyl, 1-6 carbon oxyl that phenyl, halogen that phenyl, 1-6 carbon alkyl replace replace replace；
Substituent R1Respectively represent: hydrogen, hydroxyl, amino, carbonyl, 1-6 carbon alkoxy, benzyloxy, 1-6 carbon alkylamino, benzyl amino,
Fragrant oxygroup and fragrant amido；
Substituent R2It respectively represents: hydrogen, methyl, hydroxy methylene, hydrocarbyl carboxylic ester (1-6 carbon), 1-6 carbon alkyl, aromatic radical and fragrance
Methylene.
2. claim 1 leads to formula (I) compound represented, which is characterized in that be selected from following three parts compound:
First part:
Second part (substituent R 2 is substituent group shown in first part):
Part III (substituent R 2 be respectively substituent group shown in first part and second part with Ar):
3. phenyl acetanides the answering in prevention and treatment agricultural plant disease containing chiral oxazoline shown in claim 1
With.
4. the application as required by right 3, which is characterized in that the agricultural disease is Sclerotinia sclerotiorum, rice sheath blight disease
Bacterium, Botrytis cinerea germ, rhizoctonia cerealis, fusarium graminearum, gaeumannomyces graminis, botrytis cinerea, potato evening
Epidemic disease bacterium, P. capsici, tomato early blight bacterium, fusarium moniliforme, dry rot of potato bacterium, cucumber anthracnose and water
Rice Pyricularia oryzae.
5. the compound is processed into missible oil, aqueous emulsion, microemulsion, wettable powder, water dispersion according to the purposes of right 3 and 4
Granula, suspending agent.
6. application of the phenyl acetanides containing chiral oxazoline in controlling plant diseases described in claim 1 and 2,
It is characterized in that, one of it and commercialization fungicide or multiple combinations are preparing the purposes in composite bactericide；Commercialization is killed
Microbial inoculum be selected from mandipropamid, Fluoxastrobin, pyraclostrobin, prothioconazoles, trifloxystrobin, ciproconazole, Mancozeb, epoxiconazole,
Tebuconazole, Boscalid, metalaxyl, ZEN 90160, difenoconazole, propiconazole, Bravo, tiadinil, first thiophene lure amine, different
Metsulfovax, Ningnanmycin, allyl isothiazole, flumorph, dimethomorph.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114736170A (en) * | 2022-05-20 | 2022-07-12 | 贵州大学 | Aryl amide compound containing thia (oxazoline) and preparation method and application thereof in preparing bactericide |
| CN115433141A (en) * | 2022-09-06 | 2022-12-06 | 贵州大学 | Alpha-oximido phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
| CN115557887A (en) * | 2022-11-10 | 2023-01-03 | 南京林业大学 | Synthesis of trifluoromethyl pyridine derivative based on Ugi reaction and biological activity research of trifluoromethyl pyridine derivative |
-
2018
- 2018-04-13 CN CN201810345936.6A patent/CN110372622A/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| KHRYSTYNA HERASYMCHUK 等: "Simple Modular Synthetic Approaches to Asymmetric NN′N′′, NN′C, or NN′P-Type Amido Pincer Ligands: Synthesis, Characterisation, and Preliminary Ligation Studies", 《SYNTHESIS》 * |
| OLGA A. MUKHINA等: "Oxazolines as Dual Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| SHENGKUN LI 等: "Design, Synthesis, Fungicidal Activity and Unexpected DockingModel of the First Chiral Boscalid Analogues Containing Oxazolines", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114736170A (en) * | 2022-05-20 | 2022-07-12 | 贵州大学 | Aryl amide compound containing thia (oxazoline) and preparation method and application thereof in preparing bactericide |
| CN115433141A (en) * | 2022-09-06 | 2022-12-06 | 贵州大学 | Alpha-oximido phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
| CN115433141B (en) * | 2022-09-06 | 2023-08-22 | 贵州大学 | Alpha-oximino phenylacetamide compound, preparation method thereof and application thereof as agricultural bactericide |
| CN115557887A (en) * | 2022-11-10 | 2023-01-03 | 南京林业大学 | Synthesis of trifluoromethyl pyridine derivative based on Ugi reaction and biological activity research of trifluoromethyl pyridine derivative |
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