CN108651471A - A kind of preparation method of timber sterilization antiseptic - Google Patents
A kind of preparation method of timber sterilization antiseptic Download PDFInfo
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- CN108651471A CN108651471A CN201810347814.0A CN201810347814A CN108651471A CN 108651471 A CN108651471 A CN 108651471A CN 201810347814 A CN201810347814 A CN 201810347814A CN 108651471 A CN108651471 A CN 108651471A
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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
- A01N43/48—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
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/20—Removing fungi, molds or insects
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Forests & Forestry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of preparation methods of timber sterilization antiseptic, and with m-dichlorobenzene, chloroacetic chloride, hexamethylene ketones with Enamino-esters etc. for raw material, CCl is added4、CH2Cl2, the substances such as 4 (2 base of 1H benzimidazoles) 6 (2 base of substituted-phenyl pyrimidine) alkane/benzyl thioether, disinfecting preservative is obtained by physical compounding, chemical synthesis.Sterilization antiseptic property prepared by the present invention is stablized, and has greatly improved compared to timber sterilization antiseptic on the market to the rejection ability of wood-decaying fungus, and appearance has larger application value without significant change after timber is placed for a long time.
Description
Technical field
The present invention relates to a kind of sterilization antiseptics, and in particular to a kind of dedicated sterilization antiseptic of protection timber.
Background technology
Timber is a kind of natural macromolecular material, as current four big construction materials（Steel, cement, plastics, timber）In
Unique renewable resource, is just important the raw material of industry for a long time, and timber has many good characteristics：Light weight, it is at low cost,
With short production cycle, good heat preservation performance, beautiful texture, the easy to process, sound-absorbing that can insulate against sound, shockproof, absorbable ultraviolet light etc., can be extensive
For industries such as household, wood-based plate, papermaking, weavings.Timber is easy to degrade in the case where various biotic factors act on, because of timber
Containing more starch, reduced sugar, protein, fat etc. in cell, timber is easy to occur rotten in the environment of warm moist
It is rotten, go mouldy and damage by worms.Wood degradation is essential link in the carbon nitrogen cycle in entire biosphere, but timber is processed
For industry and construction industry, the moth erosion of microorganism decomposition and pest influences the service life of timber.Poor forest resources, per capita timber
Occupancy volume is only world average level.Efficient utilize of timber resources is to alleviate the insufficient important hand of China's Forest Resources
Section, therefore, carry out protection processing to timber is particularly important with increasing its service life.
Invention content
A kind of preparation method of timber sterilization antiseptic adds with m-dichlorobenzene, chloroacetic chloride, hexamethylene ketones with Enamino-esters etc. for raw material
Enter CCl4、CH2Cl2, the substances such as 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether, lead to
Cross physical compounding, chemical synthesis obtains sterilization antiseptic, the sterilization antiseptic is strong to the rejection ability of rot fungi, in timber
Leach resistance is better than sterilization antiseptic on the market.
This approach includes the following steps：
1）Equipped with thermometer, constant pressure funnel, reflux condensing tube 250ml four-hole boiling flask in, be added 14.8 ~ 24.8 parts by weight
M-dichlorobenzene, the alchlor of 22.7 ~ 32.7 parts by weight, which stirs 0.5 h under 30 ~ 35 DEG C, 150rmp rotating speeds
Afterwards, reaction temperature is kept, then the chloroacetic chloride of 9.42 parts by weight is slowly added dropwise.After being added dropwise, temperature is slowly increased to 50 ~ 55
DEG C, continue to be stirred to react, until not having hydrogen chloride gas generation, the hexamethylene enamine assimilation of 2.18 ~ 3.18 parts by weight is then added
Object is closed, is stood after reacting 5 h.
2）By in the above-mentioned flask merging ice-water bath equipped with reaction mixture, temperature of charge is made to be down to 5 DEG C hereinafter, drop
Add the hydrochloric acid of 20 parts by weight 3mol/L to carry out acidolysis, adds the CCl of 11.4 parts by weight purifying4, 0.98 parts by weight purifying three
The CH of ethamine and the purifying of 2.12 parts by weight2Cl2, controlling rate of addition keeps the temperature change of mixture little.It will be mixed after acidolysis
It closes object and pours into beaker, control pH is 3.6, and the sterilization antiseptic 4- (1H- benzimidazolyl-2 radicals-yl)-of 1.66 parts by weight synthesis is added dropwise
Then the distilled water of 60 parts by weight is added in 6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether, solid is precipitated, and decompression filters,
It is dry, faint yellow powdery solid is obtained, the sterilization antiseptic is obtained three times with n-hexane recrystallization.
Advantageous effect：Sterilization antiseptic synthesized by the present invention can inhibit the synthesis of ergosterol in bacterial cell membrane,
So as to interfere the development of fungi attachment spore and haustorium, the growth of mycelia and the formation of spore are influenced.Wherein, m-dichlorobenzene is
Basic hydrolysis does not occur at normal temperatures for the colourless liquid with unique fragrance taste, and the compound of synthesis is to wood-decaying fungus
Rejection ability have greatly improved compared to timber sterilization antiseptic on the market, chemical property stablize, non-secondary pollution；Ring
Hexamethyleneamine ketone is generally all connected with substituent group on biologically active compound ring, and shows good activity；Sterilization
In preservative 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether introduce pyrimidine, thioether,
Amide isoreactivity substructure has desinsection, sterilization isoreactivity.Compared with timber sterilization antiseptic on the market, of the invention kills
Bacterium preservative has higher bactericidal activity, has better popularizing value.
Specific implementation mode
Embodiment 1
1）Equipped with thermometer, constant pressure funnel, reflux condensing tube（With drying tube）250ml four-hole boiling flask in, be added
The m-dichlorobenzene of 14.8 parts by weight, the alchlor of 22.7 parts by weight, the mixture stir under 30 ~ 35 DEG C, 150rmp rotating speeds
After 0.5 h, reaction temperature is kept, then the chloroacetic chloride of 9.42 parts by weight is slowly added dropwise.After being added dropwise, temperature is slowly increased to 50
~ 55 DEG C, continue to be stirred to react, until there is no hydrogen chloride gas generation.Then the hexamethylene enamine assimilation that 2.18 parts by weight are added is closed
Object is stood after reacting 5 h.
2）By in the above-mentioned flask merging ice-water bath equipped with reaction mixture, temperature of charge is made to be down to 5 DEG C hereinafter, drop
Add the hydrochloric acid of 20 parts by weight 3mol/L to carry out acidolysis, adds the CCl of 11.4 parts by weight purifying4, 0.98 parts by weight purifying three
The CH of ethamine and the purifying of 2.12 parts by weight2Cl2, controlling rate of addition keeps the temperature change of mixture little.It will be mixed after acidolysis
It closes object and pours into beaker, control pH is 3.6, and the sterilization antiseptic 4- (1H- benzimidazolyl-2 radicals-yl)-of 1.66 parts by weight synthesis is added dropwise
Then the distilled water of 60 parts by weight is added in 6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether, solid is precipitated, and decompression filters,
It is dry, faint yellow powdery solid is obtained, the sterilization antiseptic is obtained three times with n-hexane recrystallization.
Embodiment 2
Identical with embodiment 1, difference is：The m-dichlorobenzene of 15.8 parts by weight, the alchlor of 23.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.28 parts by weight.
Embodiment 3
Identical with embodiment 1, difference is：The m-dichlorobenzene of 16.8 parts by weight, the alchlor of 24.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.38 parts by weight.
Embodiment 4
Identical with embodiment 1, difference is：The m-dichlorobenzene of 17.8 parts by weight, the alchlor of 25.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.48 parts by weight.
Embodiment 5
Identical with embodiment 1, difference is：The m-dichlorobenzene of 18.8 parts by weight, the alchlor of 26.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.58 parts by weight.
Embodiment 6
Identical with embodiment 1, difference is：The m-dichlorobenzene of 19.8 parts by weight, the alchlor of 27.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.68 parts by weight.
Embodiment 7
Identical with embodiment 1, difference is：The m-dichlorobenzene of 20.8 parts by weight, the alchlor of 28.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.78 parts by weight.
Embodiment 8
Identical with embodiment 1, difference is：The m-dichlorobenzene of 21.8 parts by weight, the alchlor of 29.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.88 parts by weight.
Embodiment 9
Identical with embodiment 1, difference is：The m-dichlorobenzene of 22.8 parts by weight, the alchlor of 30.7 parts by weight is added
With the hexamethylene enamine ketone compound of 2.98 parts by weight.
Comparative example 1
Identical with embodiment 1, difference is：It is added without chloroacetic chloride.
Comparative example 2
Identical with embodiment 1, difference is：It is added without compound hexamethylene enamine ketone compound.
Comparative example 3
Identical with embodiment 1, difference is：Acidolysis without hydrochloric acid.
Comparative example 4
Identical with embodiment 1, difference is：It is added without the CCl of purifying4、CH2Cl2, triethylamine.
Comparative example 5
Identical with embodiment 1, difference is：It is added without 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-
Base)-alkane/benzyl thioether.
Comparative example 6
Identical with embodiment 1, difference is：Prepare 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-
Base)-alkane/benzyl thioether when do not adjust pH.
Comparative example 7
Identical with embodiment 1, difference is：Prepare 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-
Base)-alkane/benzyl thioether when with chloroform replace dichloromethane.
Comparative example 8
Identical with embodiment 1, difference is：It is added without CCl when preparing the sterilization antiseptic4。
Comparative example 9
Identical with embodiment 1, difference is：PH is not controlled when preparing the sterilization antiseptic.
The sterilization antiseptic prepared as follows with comparative example 1 ~ 9 to the embodiment of the present invention 1 ~ 9 is tested for the property.
The culture of strain
It prepares 5 m L physiological saline to be placed in small test tube, 121 DEG C of 30 min of high pressure sterilization after being stoppered with tampon are cooling.Various bacterium
The preparation method of kind bacteria suspension is as follows：
Corilus versicolor Quel.：The mycelia block of 5 mm of diameter is taken in the mycelia part of plating medium obtained（With agar culture
Base）It 5, is put into physiological saline, smashs to pieces, vibrated on eddy mixer, mycelia is made to evenly spread out；Trichoderma viride：With connecing
Kind needle takes a ring spore, washes in the physiological saline of test tube, vibrates test tube, spore is made to evenly spread out.
This experimentation detects the antiseptic and inhibiting bacteria function effect of sterilization antiseptic using diffusion method, rotten true by cultured two kinds
Bacterium is inoculated into same specification size（A diameter of 100mm）The timber for killing bacterium on, control two kinds of inoculated fungis bacterium circle it is straight
Diameter size is 10mm, cultivates 12h at room temperature.The timber sterilization antiseptic of 0.01g is added, to two kinds of rotten fungies（Color suede leather
Lid bacterium, Trichoderma viride）Activity be detected, measure its reaction after bacterium loop diameter size.Its inhibition such as following table.
Sterilization antiseptic carries out bacteriostasis property test
As can be seen from the above table, with m-dichlorobenzene in embodiment 1 ~ 9, alchlor and hexamethylene enamine ketone compound addition
Gradually increasing, all there is apparent reduction in the diameter of two kinds of bacterium circles of Corilus versicolor Quel. and Trichoderma viride after culture, wherein
The bacterium loop diameter of embodiment 1 is minimum, shows that sterilization antiseptic effect prepared by embodiment 1 is best, other effects are not very good.
The possible reason is the mix products of three kinds of substances disturb the catalytic action of mixed-functional oxidase in fungus body, to inhibit
The demethylation reaction of the 24- methylene dioxy lanosterol of somatic cells film ergosterol biosynthesis, makes cell inactivation.Three kinds
After material mass increases, blend proportion imbalance, synergic remove weakens, and bacteria-eliminating efficacy reduces.Comparative example 1-4 can be seen that
The addition of the substances such as compound hexamethylene enamine ketone compound can promote bacteria-eliminating efficacy, the possible reason is the substance has been contained carefully
Aliphatic acid synthesizes in bacterium.Comparative example 5 ~ 7 can be seen that sterilization antiseptic 4- (1H- benzimidazolyl-2 radicals-yl), and (substituted-phenyl is phonetic by -6-
Pyridine -2- bases) addition of-alkane/benzyl thioether improves the sterilizing ability of sterilization antiseptic, the possible reason is 4- (1H- benzo miaows
Azoles -2- bases) -6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether itself just has bactericidal property as sterilization antiseptic, and it can
To inhibit the generation of a variety of enzymes in thalline, with the compound rear generation synergic remove of other substances.Embodiment 1,8 ~ 9 can be seen that
The selection for preparing the sterilization antiseptic raw material and condition has prominent influence to sterilization antiseptic performance.
Claims (6)
1. a kind of preparation method of timber sterilization antiseptic, it is characterised in that this approach includes the following steps：
1）Equipped with thermometer, constant pressure funnel, reflux condensing tube 250ml four-hole boiling flask in, be added 14.8 ~ 24.8 parts by weight
M-dichlorobenzene, the alchlor of 22.7 ~ 32.7 parts by weight, which stirs 0.5 h under 30 ~ 35 DEG C, 150rmp rotating speeds
Afterwards, reaction temperature is kept, then the chloroacetic chloride of 9.42 parts by weight is slowly added dropwise, after being added dropwise, slowly increases temperature to 50 ~ 55
DEG C, continue to be stirred to react, until there is no hydrogen chloride gas generation,
Then the hexamethylene enamine ketone compound of 2.18 ~ 3.18 parts by weight is added, is stood after reacting 5 h；
2）By in the above-mentioned flask merging ice-water bath equipped with reaction mixture, temperature of charge is made to be down to 5 DEG C hereinafter, being added dropwise 20
The hydrochloric acid of parts by weight 3mol/L carries out acidolysis, adds the CCl of 11.4 parts by weight purifying4, 0.98 parts by weight purifying triethylamine
With the CH of 2.12 parts by weight purifying2Cl2；
Mixture after acidolysis is poured into beaker, control pH is 3.6, and the sterilization antiseptic 4- of 1.66 parts by weight synthesis is added dropwise
(1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether, is then added the distillation of 60 parts by weight
Solid is precipitated in water, and decompression filters, dry, obtains faint yellow powdery solid, and it is anti-to obtain the sterilization three times with n-hexane recrystallization
Rotten agent.
2. according to a kind of preparation method of timber sterilization antiseptic, characterization step 1 described in claim 1）Middle ring hexamethyleneamine
The preparation method of ketone compound：At ambient temperature, by the aniline of 1 parts by weight, 5,5- dimethyl -1,3- rings of 1.5 parts by weight
Acetyl butyryl and 0.2 parts by weight LiSiO4/SiO2It is added in 50mL there-necked flasks, and is stirred in the case where magnetic force whisks device 150rmp rotating speeds
It mixes, it is 80 DEG C to heat there-necked flask and keep temperature, and upper end connects condenser pipe reflux, reacts about 10 min of min~15.
3. after finding that at least one raw material has reacted, the temperature of there-necked flask is reduced to 25 DEG C, 20 parts by weight are added into bottle
Caproic acid second vinegar, stirring 5min makes product all dissolve, and suction filtration isolates catalyst, filtrate revolving, crude product EtOH/H2
(V:V=1:1) recrystallization purifying obtains product hexamethylene enamine ketone compound.
4. according to a kind of preparation method of timber sterilization antiseptic, characterization step 2 described in claim 1）Middle CCl4Purifying
Process：The potassium hydroxide for weighing 6 parts by weight is dissolved in the solution that 8 parts by weight of deionized water and 10 parts by weight of ethanol are configured to, will
100 parts by weight carbon tetrachloride are mixed with the solution of preparation and are washed after 50~60 DEG C acutely concussion 0.5h, and potassium hydroxide is matched
The manufactured solution amount of halving is mixed with carbon tetrachloride to repeat to shake primary, separates carbon tetrachloride, is first washed with water, then with dense sulphur on a small quantity
Then pickling is washed with water, is dried with anhydrous calcium chloride to colourless, distillation obtains anhydrous carbon tetrachloride.
5. according to a kind of preparation method of timber sterilization antiseptic, characterization step 2 described in claim 1）Middle CH2Cl2Purifying
Process：150 weight parts Methylene chlorides are measured in separatory funnel, the 15 parts by weight concentrated sulfuric acids, concussion are added, stratification divides
20 parts by weight of deionized water are added after going out dichloromethane layer, shake, stratification, then washed with 10 parts by weight saturated sodium carbonate solutions
It washs, then is washed with 20 parts by weight of deionized water, stratification is dried with anhydrous calcium chloride, and distillation obtains anhydrous methylene chloride.
6. according to a kind of preparation method of timber sterilization antiseptic, characterization step 2 described in claim 1）Middle sterilization and anticorrosion
The synthetic method of agent 4- (1H- benzimidazolyl-2 radicals-yl) -6- (substituted-phenyl pyrimidine -2-base)-alkane/benzyl thioether is：It is burnt in round bottom
20 parts by weight of isopropyl alcohol are added in bottle, 0.4 part by weight of metal sodium is cut into small pieces and is slowly added into isopropanol, heating stirring,
0.36 parts by weight thiocarbamide is added after metallic sodium is completely dissolved, adds (E) -1- (1H- benzimidazolyl-2 radicals-yl)-of 1 parts by weight
3- phenyl -2- propylene -1- ketone, is heated to reflux, and reacts natural cooling after 6 h, and reaction solution is rotated and removes solvent, and 40 weight are added
The distillation water dissolution of part adjusts pH to 5~6 with dilute hydrochloric acid, and generation is a large amount of to be precipitated, and product is placed in burning by suction filtration, washing after drying
In bottle, 0.12 parts by weight NaOH and 10 parts by weight acetonitriles are added, it is 80% that 3 parts by weight fluoroanilines, which are dissolved in 5 parts by weight mass fractions,
Acetonitrile solution in, be slowly dropped in round-bottomed flask when 40 DEG C under stirring, be heated to reflux after being added dropwise to complete, react 5 h mistakes
It filters out and precipitates, filtrate is rotated, washed after the dissolving of 100 weight parts Methylene chlorides is added, dry, revolving obtains oil product,
Pass through column chromatography (acetone:Petroleum ether=1:8) separating-purifying obtains compound 4- (1H- benzimidazolyl-2 radicals-yl) (phenyl is phonetic by -6-
Pyridine -2- bases) -/benzyl thioether.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187924A (en) * | 2016-07-11 | 2016-12-07 | 南京林业大学 | Triazole class compounds and its preparation method and application |
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2018
- 2018-04-18 CN CN201810347814.0A patent/CN108651471A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187924A (en) * | 2016-07-11 | 2016-12-07 | 南京林业大学 | Triazole class compounds and its preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| 晋清栋: "含嘧啶硫醚/嘧啶硫乙酰胺结构的苯并咪唑衍生物的合成及抑菌活性研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 高云云: "环己烯胺酮类化合物的合成与杀菌活性研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
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