CN106831476B - Polysubstituted 2- hydroxyl -1,2- dihydro naphthalenone with bactericidal activity and preparation method thereof - Google Patents
Polysubstituted 2- hydroxyl -1,2- dihydro naphthalenone with bactericidal activity and preparation method thereof Download PDFInfo
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- CN106831476B CN106831476B CN201710081864.4A CN201710081864A CN106831476B CN 106831476 B CN106831476 B CN 106831476B CN 201710081864 A CN201710081864 A CN 201710081864A CN 106831476 B CN106831476 B CN 106831476B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
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Abstract
One kind has the polysubstituted 2- hydroxyl -1,2- dialin ketone derivatives of bactericidal activity.Logical formula (I) is the hydroxyl dialin ketone derivatives with bactericidal activity, specifically:R in formula1For 4- chlorphenyl, 4- bromophenyl, R1For tert-butyl, normal-butyl, cyclohexyl.Above compound has preferable inhibitory activity to penicillium italicum, penicillium digitatum and rice blast fungus, can be used as fungicide.
Description
Technical field
The present invention relates to 2- hydroxyl -1,2- dialin ketone derivatives and it answer as the effective component of fungicide
With.
Background technique
Bread is the staff of life, and the safety in production of grain is related to national economy, is life-and-death big problem.The production of grain
It is be unable to do without pesticide, safety, low toxicity, efficient pesticide are the strong guarantees of grain good harvest, and fungicide is the important composition of pesticide
Part plays key player in the development history of pesticide.But the bacterium and fungi that constantly make a variation and various different conditions
Under to fungicide using limitation demand, research and develop more with more preferable bacteriostatic activity new type bactericide, be promote kill
The key of microbial inoculum development.There is good bactericidal activity in view of hydrogenated naphthalene ketones derivant, especially contain on hydrogenation naphthalenone ring
There is such compound of hydroxyl.The preparation and its bactericidal activity for studying novel hydroxy group naphthalenone analog derivative have important
Meaning.
Summary of the invention
It is a primary object of the present invention to explore the good compound of bactericidal properties, the 2- hydroxyl-with bactericidal activity is provided
1,2- dialin ketone derivatives.
The invention proposes 2- hydroxyl -1,2- dialin ketone derivatives (I):
Wherein, substituent R1For the phenyl that 4- chlorine or 4- bromine replace, R2For tert-butyl, normal-butyl or cyclohexyl.
The compound that the present invention provides above-mentioned formula (I) has penicillium italicum, penicillium digitatum and rice blast fungus preferable
Inhibitory activity, thus can be used as the effective component of fungicide.
Synthetic method of the present invention is with keto-aldehyde, isonitrile by quaternary phosphonium salt carboxylic acid in the presence of base with " one kettle way " system of reacting
Standby, in formula (II) R1And R2It is identical as the definition in logical formula (I).Specific synthesis 2- hydroxyl -1,2- dialin ketone sterilization
The method of agent, the method includes following synthesis paths:
It the described method comprises the following steps:
Toluene is added into reaction flask, weighs logical formula (II) compound represented and is added in reaction flask, is added twice and works as
The triethylamine of amount stirs 2-5 hour as alkali at 50 DEG C, and after the reaction was completed, reaction solution sloughs solvent under reduced pressure, residual
Object column chromatographs to obtain the target compound of logical formula (I).
The experimental procedure of (II) of synthesis material:
The compound quaternary phosphonium salt carboxylic acid (III) and keto-aldehyde (IV) and isonitrile (V) 1:1:1 in molar ratio, at 30 DEG C instead
It answers, reaction dissolvent is methylene chloride, and after reaction 24 hours, solvent changes toluene into, and triethylamine is added, and dosage is bromine band carboxylic acid
(III) 1.2 times.Reaction is stirred 2-5 hours at 50 DEG C, and after the reaction was completed, reaction solution sloughs solvent, residue under reduced pressure
Column chromatographs to obtain the target compound of logical formula (II).
Specific embodiment
The preparation and application effect of compound in (I) formula of the invention are further illustrated below with reference to embodiment.
Instrument and reagent:
Fusing point is measured with X4 type melting point apparatus (production of Beijing third optical instrument factory), and thermometer is not calibrated；1H NMR and13600 type 600MHz core of C NMR 400 type 400MHz Nuclear Magnetic Resonance of Varian Mercury or Varian Mercury
Magnetic resonance device measurement, deuterated chloroform (CDCl3) or deuterated dimethyl sulfoxide (DMSO-d6) it is solvent, TMS is internal standard；MS is used
The measurement of FinniganTrace mass spectrograph；Elemental analysis is measured using Vario EL III elemental analyser；Agents useful for same is domestic
(or import) chemistry is pure or analysis is pure.Solvent toluene is to be evaporated dry mistake through overweight, and triethylamine is also processed by steaming again.
Embodiment 1
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parachloroacetophenone aldehyde (IV) (1mmol) and tertiary fourth are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.313g white crystal, yield 85%.
Elemental analysis: 68.43 H% of measured value C%, 5.39 N% 3.87
68.20 H% of calculated value C%, 5.45 N% 3.79
1H NMR(CDCl3, 600MHz) δ (ppm) 8.06-7.25 (m, 8H, Ar-H), 6.99 (s, 1H ,=CH), 6.58 (s,
1H,NH),5.21(s,1H,OH),1.26(s,9H,3CH3).
MS (EI, 70eV): m/z (%)=369 (1) [M+],325(6),270(100),241(56).
Embodiment 2
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parachloroacetophenone aldehyde (IV) (1mmol) and hexamethylene are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.329g white crystal, yield 83%.
Elemental analysis: 69.97 H% of measured value C%, 5.41 N% 3.70
69.78 H% of calculated value C%, 5.60 N% 3.54
1H NMR(CDCl3, 600MHz) δ (ppm) 8.05-7.20 (m, 8H, Ar-H), 6.98 (s, 1H ,=CH), 6.71 (t,
J=6.6Hz, 1H, NH), 5.28 (s, 1H, OH), 3.69 (t, J=8.4Hz, 1H, CH), 1.86-0.80 (m, 10H, 5CH2).
MS (EI, 70eV): m/z (%)=395 (4) [M+],351(19),270(100).
Embodiment 3
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parachloroacetophenone aldehyde (IV) (1mmol) and positive fourth are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.280g white crystal, yield 76%.
Elemental analysis: 65.33 H% of measured value C%, 5.61 N% 3.86
68.20 H% of calculated value C%, 5.45 N% 3.79
1H NMR(CDCl3, 600MHz) δ (ppm) 8.08-7.21 (m, 8H, Ar-H), 6.97 (s, 1H ,=CH), 6.66 (s,
1H,NH),5.38(s,1H,OH),3.62–0.81(m,9H,3CH2,CH3).
MS (EI, 70eV): m/z (%)=369 (1) [M+],325(3),270(100).
Embodiment 4
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parabromoacetophenone aldehyde (IV) (1mmol) and tertiary fourth are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.323g white crystal, yield 78%.
Elemental analysis: 61.13 H% of measured value C%, 4.59 N% 3.57
60.88 H% of calculated value C%, 4.87 N% 3.38
1H NMR(CDCl3, 600MHz) δ (ppm) 8.06-7.22 (m, 8H, Ar-H), 6.98 (s, 1H ,=CH), 6.57 (s,
1H,NH),5.21(s,1H,OH),1.26(s,9H,3CH3).
MS (EI, 70eV): m/z (%)=413 (1) [M+],315(3),245(100).
Embodiment 5
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parabromoacetophenone aldehyde (IV) (1mmol) and hexamethylene are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.361g white crystal, yield 82%.
Elemental analysis: 62.91 H% of measured value C%, 4.77 N% 3.31
62.74 H% of calculated value C%, 5.04 N% 3.18
1H NMR(CDCl3, 600MHz) δ (ppm) 8.06-7.17 (m, 8H, Ar-H), 6.99 (s, 1H ,=CH), 6.71 (t,
J=6.6Hz, 1H, NH), 5.28 (s, 1H, OH), 3.68 (t, J=8.4Hz, 1H, CH), 1.90-0.83 (m, 10H, 5CH2).
MS (EI, 70eV): m/z (%)=439 (8) [M+],395(18),314(100),286(38),256(64).
Embodiment 6
Preparation
Quaternary phosphonium salt carboxylic acid (III) (1mmol), parabromoacetophenone aldehyde (IV) (1mmol) and positive fourth are added into 50mL flask
Base isonitrile (V) (1mmol), reacts at 30 DEG C, and reaction dissolvent is methylene chloride, and solvent changes toluene into after reaction 24 hours, adds
Enter triethylamine (2mmol), continues to stir 3 hours under 50 DEG C of reactions, after the reaction was completed, reaction solution sloughs solvent under reduced pressure,
Residue column chromatographs to obtain 0.302g white crystal, yield 73%.
Elemental analysis: 60.97 H% of measured value C%, 4.98 N% 3.52
60.88 H% of calculated value C%, 4.87 N% 3.38
1H NMR(CDCl3, 600MHz) δ (ppm) 8.05-7.22 (m, 8H, Ar-H), 6.99 (s, 1H ,=CH), 6.90 (t,
J=1.8Hz, 1H, NH), 5.31 (s, 1H, OH), 3.36-3.04 (m, 2H, NCH2),1.53–1.34(m,2H,CH2),1.34–
1.18(m,2H,CH2), 0.90 (t, J=7.8Hz, 3H, CH3).
MS (EI, 70eV): m/z (%)=413 (1) [M+],371(13),314(100),286(44).
Embodiment 7
Bactericidal activity experiment (contains toxic medium method)
Liquor strength 100ppm takes strain agar block with 5mm punch, and mycelia is inoculated with down will contain candidate drug
In PDA culture medium, it is placed in the center of round culture medium, cutting not slide strain agar block, in order to avoid pollution culture medium.Each to
Sample is inoculated with three, is to be placed on biochemical culture to blank photo with the culture medium without drug but containing same concentrations DMSO
After cultivating 3~5 days at 25 DEG C in case, the diameter of the bacterium colony on culture medium is measured.Pass through the comparison with above-mentioned blank control group
To observe the influence that sample to be tested grows mycelia, the inhibiting rate that calculating sample to be tested grows bacterium colony at 100mg/L.Inhibit
Rate (%)=[(blank control colony diameter-sample to be tested colony diameter)/(blank colony diameter-punch diameter)] ×
100%.Table 1 is the measurement result of part of compounds (I).
Table 1: the bacteriostatic activity test result of compound (I)
As can be seen from the above Table 1, compound represented by formula of the invention (I) is to penicillium digitatum (Penicillium
Digitatum), penicillium italicum (Penicillium italicum) and rice blast fungus (Magnaporthe grisea) have
Preferable inhibitory activity.It is wherein best with compound (I) -6 effects.
The compound of the present invention is as fungicide in use, the load that can will allow in the compound of the present invention and other plant protection
Body or diluent mixing, are modulated into usually used various dosage forms, such as mixture, granule, aqueous emulsion whereby to use,
It can also be used in mixed way or be used in combination simultaneously with other pesticides such as fungicide, Insecticides (tech) & Herbicides (tech) and plant growth regulator.
Claims (4)
1. the preparation method of a kind of polysubstituted 2- hydroxyl -1,2- dialin ketone derivatives, which is characterized in that have logical formula (I)
The structure of expression:
Wherein, R1For the phenyl that 4- chlorine or 4- bromine replace, R2For tert-butyl, normal-butyl or cyclohexyl, the polysubstituted 2- hydroxyl
The preparation method of base -1,2- dialin ketone derivatives, synthesis path are as follows:
Compound quaternary phosphonium salt carboxylic acid (III) and keto-aldehyde and isonitrile 1:1:1 in molar ratio, react, reaction dissolvent two at 30 DEG C
Chloromethanes, after reaction 24 hours, solvent changes toluene into, and temperature is increased to 50 DEG C, and triethylamine is added, and mole dosage is quaternary phosphonium salt carboxylic
Twice of sour (III), the reaction was continued 2-5 hours, and after the reaction was completed, reaction solution sloughs solvent, residue column chromatography under reduced pressure
Obtain the target compound of logical formula (I).
2. the preparation method of polysubstituted 2- hydroxyl -1,2- dialin ketone derivatives described in claim 1, which is characterized in that
The keto-aldehyde is parachloroacetophenone aldehyde, parabromoacetophenone aldehyde.
3. the preparation method of polysubstituted 2- hydroxyl -1,2- dialin ketone derivatives described in claim 1, which is characterized in that
The isonitrile is tert-butyl isonitrile, cyclohexyl isonitrile or normal-butyl isonitrile.
4. the preparation-obtained polysubstituted 2- hydroxyl -1,2- dialin ketone derivatives of any one of claim 1-3 refer in preparation
Shape Penicillium notatum Penicillium digitatum, penicillium italicum Penicillium italicum and rice blast fungus
Application on the fungicide of Magnaporthe grisea.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619492A (en) * | 1950-02-10 | 1952-11-25 | Gen Aniline & Film Corp | Soluble onium salts of halogenmethylated dibenzanthronyls |
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2017
- 2017-02-15 CN CN201710081864.4A patent/CN106831476B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619492A (en) * | 1950-02-10 | 1952-11-25 | Gen Aniline & Film Corp | Soluble onium salts of halogenmethylated dibenzanthronyls |
Non-Patent Citations (4)
| Title |
|---|
| Atom, atom-type, and total nonstochastic and stochastic quadratic fingerprints: a promising approach for modeling of antibacterial activity;Yovani Marrero-Ponce等;《Bioorganic & Medicinal Chemistry》;20051231;第13卷(第8期);第2881-2899页 * |
| Electroreduction of quinones under aprotic conditions;Belen Batanero;《Electrochimica Acta》;20090309;第54卷;第4872-4879页 * |
| Ketene-S,S-gem dithiols. Interaction with heterogeneous radicals and studyof the effect of products as antimicrobial agents;Zayed, Salem E.等;《Egyptian Journal of Chemistry》;19901231;第31卷(第1期);参见CAPLUS库摘要和著录项目 * |
| Structure and antimicrobial activity of 2-hydroxycinnamic aldehyde derivatives;Andreeva, I. M.等;《Khimiko-Farmatsevticheskii Zhurnal》;19851231;第19卷(第1期);第29-31页 * |
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