CN109942591A - A kind of compound oxolinic acid with bactericidal activity is in application agriculturally - Google Patents
A kind of compound oxolinic acid with bactericidal activity is in application agriculturally Download PDFInfo
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- CN109942591A CN109942591A CN201910307325.7A CN201910307325A CN109942591A CN 109942591 A CN109942591 A CN 109942591A CN 201910307325 A CN201910307325 A CN 201910307325A CN 109942591 A CN109942591 A CN 109942591A
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Abstract
The invention discloses a kind of compounds with bactericidal activity in new opplication agriculturally, which is oxolinic acid, structural formula are as follows:
Description
Technical field
The present invention relates to agricultural disease prevention and control field, specifically a kind of compound oxolinic acid with bactericidal activity is in agricultural
On application.
Background technique
Oxolinic acid (Oxolinic Acid) also known as Ao Suolin acid, oxolinic acid etc., chemical name: 1- ethyl -6,7- methylene
Oxygroup -4- copper 8-hydroxyquinolinate -3- carboxylic acid.Raw medicine low toxicity, has no stimulation of the skin, has slight stimulation effect to eyes.No sensitization is made
With animal experiment is without teratogenesis, carcinogenic, mutagenesis.Oxolinic acid category second generation quinolinones fungicide, mechanism of action are to pass through
Inhibit DNA helicase to influence the normal morphology of DNA and function (normal replication) and achieve the purpose that antibacterial, DNA is with height
The form that degree helix-coil folds is present in thallus, if do not rolled up poly-.Then its length considerably beyond cell several times, at all
It can not be contained in cell wall, it also can not normal DNA replication dna, transhipment and recombination.The effect of DNA helicase is exactly to protect DNA
The poly- state of volume for holding height, due to quinolones antibacterial action mechanism and lactams, other antibiotic such as aminoglycoside are made
It is different with mechanism, therefore without obvious crossing drug resistant phenomenon.
There is document report oxolinic acid to have good preventive effect to cucumber bacterial angular leaf spot and bacterial wilt of tomato, cucumber is bacillary
Angular leaf spot is infected by bacterium pseudomonas syringae cucumber angle spot pvs oryzae and oryzicola to be caused, and bacterial wilt of tomato is by the green withered false unit cell of bacterium
Bacterium, which is infected, to cause.Mango bacterial angular leaf spot of the present invention is infected by rape Xanthomonas campestris mango pvs oryzae and oryzicola to be caused,
Common bacterial blight of bean is infected by xanthomonas to be caused, and soft rot of cabbage is caused by Erwinia thallus infects, the white leaf of rice
Blight is caused by the raw pvs oryzae and oryzicola of rice Xanthomonas campestris rice infects, and citrus bacterial canker disease is caused by ecliptic pole hair bacillus is infected, potato
For balck shank caused by the black shin subspecies bacterial invasion of carrot soft rot Erwinia potato, rice basal stem rot belongs to thin by erwinia
Caused by bacterium Erwinia corn pvs oryzae and oryzicola infects, canker of pear is the macaque caused by erwinia category erwinia amylovora infects
Peach canker is caused by the false single pole bacterium Kiwi berry pvs oryzae and oryzicola of cloves infects.
The register information about oxolinic acid as pesticide not yet domestic at present.
Summary of the invention
The purpose of the present invention is to provide a kind of compound oxolinic acid with bactericidal activity is in new opplication agriculturally.Hair
Bright people shows good inhibiting effect to plurality of plant diseases by largely raw experiment discovery oxolinic acid of surveying.The present invention use with
Lower technical solution:
A kind of compound oxolinic acid with bactericidal activity is in application agriculturally, the structure of the compound oxolinic acid
Formula are as follows:
The compound is white for biocontrol of mango bacterial angular leaf spot, common bacterial blight of bean, soft rot of cabbage, rice
Leaf blight, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and Prospect on Kiwifruit Bacterial Canker.
The oxolinic acid is configured to allow on pesticide any one as active constituent with insecticides adjuvant, filler or solvent
Any one dosage form allowed in kind dosage form or the oxolinic acid compound and other agriculture chemical compounding city pesticides.
The preferred suspending agent of the dosage form, wettable powder, water dispersible granules, granule, aqueous emulsion, microemulsion or ultralow
Volume liquids.
Mass percent of the compound oxolinic acid in above-mentioned dosage form is 1-80%.
The dosage of the compound oxolinic acid is 30-60g a.i./hm2。
The present invention is on the basis of many experiments, it was found that oxolinic acid is in biocontrol of mango bacterial angular leaf spot, Kidney bean bacterium
Property epidemic disease, soft rot of cabbage, bacterial blight of rice, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and
There is effect outstanding on Prospect on Kiwifruit Bacterial Canker, is nuisanceless as fungicide dosage is few, the lasting period is long, is not easy to produce resistance
The outstanding medicament of fruits and vegetables production.
Specific embodiment
Technical solution of the present invention and technical effect are described further below with reference to specific embodiment.
Embodiment of the present invention is not limited to the embodiment the range of statement.
The method that this experiment is combined using indoor bactericidal activity measurement and field trial.First pass through indoor bactericidal activity survey
It is fixed, then field trial is carried out, specific implementation is as follows.
The indoor bactericidal activity of 1 oxolinic acid of embodiment measures
Indoor inhibitory effect measuring method: using Nephelometric Determination bactericidal composition to mango bacterial angular leaf spot, Kidney bean
Bacterial epidemic disease, soft rot of cabbage, bacterial blight of rice, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, pears branch are withered
The inhibiting effect of disease and Prospect on Kiwifruit Bacterial Canker.In accordance with national sector standard, " NYT1156.16-2006 pesticide indoor biological is surveyed for test
Determine the 16th part of test rule fungicide: inhibiting bacterial growth amount test turbidity method ", the medicament for being diluted to various concentration is female
After mixing fullys shake, the 250ml specification triangular flask that 50ml NB culture medium is housed is added in the medicament mother liquor of different volumes by liquid
In, it is made into the pastille culture medium of various concentration, control plus same volume sterile water, is mixed well rear spare.By cultured germ
It is diluted to 100NTU.Every bottle of pastille culture medium is inoculated with 50 μ L seed liquors, after 30 DEG C of 200rpm cultures for 24 hours, surveys each bottle respectively
Muddy angle value.The data input Excel table measured, is calculated using the following equation medicament and presses down at various concentrations to the growth of germ
Rate processed.
Oxolinic acid is carried out to indoor bactericidal determination of activity according to the method described above, calculates EC50, the data measured such as 1 institute of table
Show.
Indoor bactericidal activity of 1 oxolinic acid of table to 9 kinds of bacteriosis
Table 1 show oxolinic acid to mango bacterial angular leaf spot, common bacterial blight of bean, soft rot of cabbage, the white leaf of rice
This 9 bacterium germs of blight, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and Prospect on Kiwifruit Bacterial Canker
Indoor biometrics are as a result, EC50Value is in 2.5mg/L hereinafter, bactericidal effect protrusion, it is good to show that oxolinic acid has at bactericidal aspect
Effect.
20% oxolinic acid suspending agent, 80% oxolinic acid has been respectively prepared by experimenter of the present invention for oxolinic acid
Wettable powder, 12% oxolinic acid water dispersible granules, 1% oxolinic acid granule, 5% oxolinic acid aqueous emulsion, 25% oxolinic acid are micro-
Emulsion and 20% oxolinic acid ultra low volume liquids carry out the field efficacy experiment of this 9 kinds of bacteriosises.Implement below with reference to preparation
Field efficacy experimental conditions of the pesticidal preparations that example explanation is prepared using oxolinic acid as effective component to eight kinds of above-mentioned bacteriums.
The pesticidal preparations embodiment of preparation is as follows:
One: 20% oxolinic acid suspending agent of example of formulations
Oxolinic acid 20%, lignosulfonates 2%, fatty alcohol polyoxyethylene ether 3%, ethylene glycol 5%, aluminium-magnesium silicate 1%,
Xanthan gum 0.15%, organic silicon defoamer 0.4%, water supplies 100%.
Two: 80% oxolinic acid wettable powder of example of formulations
Oxolinic acid 80%, naphthalene sulfonate 5%, styrylphenol polyoxyethylene ether phosphate 3%, lauryl sodium sulfate
2%, white carbon black 4%, kaolin supplies 100%.
Three: 12% oxolinic acid water dispersible granules of example of formulations
Oxolinic acid 12%, lignosulfonates 3%, alkyl polyoxyethylene sulfate salt 3%, white carbon black 3%, sodium sulphate
10%, polyvinyl alcohol 0.1%, kaolin supplies 100%.
Four: 1% oxolinic acid granule of example of formulations
Oxolinic acid 1%, polycarboxylate 2%, calcium lignosulfonate 4%, polyvinyl alcohol 3.5%, polyester resin 0.5%, Ah
Primary glue 2% is drawn, brick slag is mended to 100%.
Five: 5% oxolinic acid aqueous emulsion of example of formulations
Oxolinic acid 5%, dimethyldecamide 8%, dimethylbenzene 5%, phenethyl phenol polyoxyethylene poly-oxygen propylene aether 4%, rouge
Fat alcohol polyoxyethylene ether formaldehyde condensation products sulfate 2.5%, urea 5%, water supplies 100%.
Six: 25% oxolinic acid microemulsion of example of formulations
Oxolinic acid 25%, cyclohexanone 10%, dimethyldecamide 10%, fatty alcohol polyoxyethylene ether 3, fatty alcohol polyoxy second
Alkene ether formaldehyde condensation products sulfate 5%, calcium dodecyl benzene sulfonate 4%, water supplies 100%.
Seven: 20% oxolinic acid ultra low volume liquids of example of formulations
Oxolinic acid 20%, dimethyldecamide 15%, fatty alcohol polyoxyethylene ether 4%, calcium dodecyl benzene sulfonate 5%,
Solvent naphtha supplies 100%.
By above-mentioned pesticidal preparations embodiment to mango bacterial angular leaf spot, common bacterial blight of bean, soft rot of cabbage, water
The bacterial blight of rice, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and Prospect on Kiwifruit Bacterial Canker carry out field
Pharmacodynamic test.
The experiment of 2 biocontrol of mango bacterial angular leaf spot field efficacy of embodiment
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is that 6% spring thunder is mould
Plain wettable powder and blank clear water.
2. test method: Experimental Area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in June, 2018 in the Compounds in Dongfang City of Hainan Province town Ba Suo, by effective component 2g, 3g and 4g per acre
It is watered carry out even spraying, is administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 2 after medicine:
2 oxolinic acid of table is to mango bacterial angular leaf spot pharmacodynamic test
From table 2 it can be seen that oxolinic acid pesticidal preparations are better than comparison medicament to the control efficiency of mango bacterial angular leaf spot
6% kasugarnycin wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that evil quinoline
Sour pesticidal preparations are to crop safety without phytotoxicity.
Embodiment 3 prevents and treats the experiment of common bacterial blight of bean field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is raw bacterium in 3%
Plain wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in July, 2018 in Tangshan, Hebei Province Leting County Furukawa township, by effective component 2g per acre,
3g and 4g is watered carry out even spraying, is administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 3 after medicine:
3 oxolinic acid of table is to common bacterial blight of bean pharmacodynamic test
From table 3 it can be seen that oxolinic acid pesticidal preparations are better than comparison medicament 3% to the control efficiency of common bacterial blight of bean
Zhongshengmycin wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that this dosage
Under oxolinic acid pesticidal preparations to crop safety without phytotoxicity.
Embodiment 4 prevents and treats the experiment of soft rot of cabbage field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is raw bacterium in 3%
Plain wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in November, 2017 in Hebei province Zhangjiakou City Huaian County, by effective component 2g, 3g per acre
It is watered carry out even spraying with 4g, is administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 4 after medicine:
4 oxolinic acid of table is to soft rot of cabbage pharmacodynamic test
From table 4, it can be seen that oxolinic acid pesticidal preparations are raw better than in comparison medicament 3% to the control efficiency of soft rot of cabbage
Rhzomorph wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that under this dosage
Oxolinic acid pesticidal preparations are to crop safety without phytotoxicity.
Embodiment 5 prevents and treats the experiment of bacterial blight of rice field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is that 20% leaf is withered
Azoles wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in May, 2018 in Shaoxing, Zhejiang Province city, the town Hui Shan, Xinchang, by effective component 2g per acre,
3g and 4g is watered carry out even spraying, is administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 5 after medicine:
5 oxolinic acid of table is to rice bacterial leaf spot pharmacodynamic test
As can be seen from Table 5, oxolinic acid pesticidal preparations are better than comparison medicament 20% to the control efficiency of bacterial blight of rice
Yekuzuo wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that under this dosage
Oxolinic acid pesticidal preparations to crop safety without phytotoxicity.
Embodiment 6 prevents and treats the experiment of citrus bacterial canker disease field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is 80% second garlic
Plain missible oil and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is in in September, 2017, in Guangxi province Bose City Lingyun County, township, the Yao nationality is carried out inwardly, by effective per acre
Ingredient 2g, 3g and 4g are watered carry out even spraying, are administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table after medicine
6:
6 oxolinic acid of table is to citrus bacterial canker disease pharmacodynamic test
As can be seen from Table 6, oxolinic acid pesticidal preparations are better than 80% second of comparison medicament to the control efficiency of citrus bacterial canker disease
Allicin emulsion prevention effect, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that the oxolinic acid under this dosage
Pesticidal preparations are to crop safety without phytotoxicity.
Embodiment 7 prevents and treats the experiment of blakleg of potato field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is 58% first
White mancozeb wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in April, 2017 in the Chengde City, Hebei Province Longhua County town Bu Gugou, by effective component per acre
2g, 3g and 4g are watered carry out even spraying, are administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 7 after medicine:
7 oxolinic acid of table is to blakleg of potato pharmacodynamic test
As can be seen from Table 7, oxolinic acid pesticidal preparations are better than comparison medicament 58% to the control efficiency of blakleg of potato
First frost mancozeb wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that this agent
Oxolinic acid pesticidal preparations under amount are to crop safety without phytotoxicity.
Embodiment 8 prevents and treats the experiment of rice basal stem rot field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is 3% first frost
Hymexazol aqua and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in in September, 2017 in Jiangsu Province, the town Ba Tan, Yancheng City Binhai County, by effective component per acre
2g, 3g and 4g are watered carry out even spraying, are administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 8 after medicine:
8 oxolinic acid of table is to rice basal stem rot pharmacodynamic test
As can be seen from Table 8, oxolinic acid pesticidal preparations are better than 3% first of comparison medicament to the control efficiency of rice basal stem rot
White hymexazol aqua control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that under this dosage
Oxolinic acid pesticidal preparations are to crop safety without phytotoxicity.
Embodiment 9 prevents and treats the experiment of canker of pear field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament is 58% first
White mancozeb wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment in August, 2018 Xinjiang Uygur Autonomous Regions Bayangolmongol Autonomous Prefecture Korla City Ah
The township Wa Ti carries out, and is watered carry out even spraying by effective component 2g, 3g and 4g per acre, is administered 1 time altogether, 7 days, 14 days and 21 after medicine
Its prevention and treatment checked the results are shown in Table 9:
9 oxolinic acid of table is to canker of pear pharmacodynamic test
As can be seen from Table 9, oxolinic acid pesticidal preparations are better than 58% first of comparison medicament to the control efficiency of canker of pear
White mancozeb wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that this dosage
Under oxolinic acid pesticidal preparations to crop safety without phytotoxicity.
Embodiment 10 prevents and treats the experiment of Prospect on Kiwifruit Bacterial Canker field efficacy
1. experiment process: this experiment sets three concentration for the treatment of according to the difference of ingredient respectively, and comparison medicament was 47% spring
Thunder Cupravit wettable powder and blank clear water.
2. test method: test area is each cell 66.7m2, it is repeated 3 times；Preventive effect after investigating and be administered before application
Investigation method are as follows: 5 points of grab sample in experiment process area carry out severity Scaling, meter according to national field trial relevant criterion
Calculate preventive effect.
Present invention experiment is carried out in in August, 2018 in Xi'an City, Shanxi Province Zhouzhi County Jixian county town, by effective component per acre
2g, 3g and 4g are watered carry out even spraying, are administered 1 time altogether, the prevention and treatment checked in 7 days, 14 days and 21 days the results are shown in Table 10 after medicine:
10 oxolinic acid of table is to Prospect on Kiwifruit Bacterial Canker pharmacodynamic test
As can be seen from Table 10, oxolinic acid pesticidal preparations are better than comparison medicament 47% to the control efficiency of Prospect on Kiwifruit Bacterial Canker
Spring thunder Cupravit wettable powder control efficiency, and the lasting period of oxolinic acid pesticidal preparations is longer, test result also indicates that this agent
Oxolinic acid pesticidal preparations under amount are to crop safety without phytotoxicity.
From above 10 raw embodiments of surveying it is found that oxolinic acid can be made into suspending agent, wettable powder as pesticide activity component
Agent, water dispersible granules, granule, aqueous emulsion, microemulsion or ultra low volume liquids, to mango bacterial angular leaf spot, Kidney bean bacterium
Property epidemic disease, soft rot of cabbage, bacterial blight of rice, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and
Prospect on Kiwifruit Bacterial Canker has significant control efficiency, and bactericidal effect is obvious, compensates for the blank of oxolinic acid Pesticide use at home,
Quinolinones fungicide resistance is low, will not generate mutual resistance with other drugs, while to crop safety, the lasting period is long, saves
Power is time saving, improves the service efficiency of pesticide, is the favourable agents for preventing and treating such bacteriosis, is widely used in production
Prospect.
In conclusion the compound with bactericidal activity of the invention is oxolinic acid, progress indoor bactericidal activity survey first
Examination, then field efficacy test is carried out, bactericidal effect is significant.Simultaneously to crop safety, the lasting period is long, meets the safety of pesticidal preparations
Property require.
Compound oxolinic acid with bactericidal activity of the invention agriculturally use by specific example into
Description is gone, those skilled in the art can use for reference the content of present invention, and the links such as appropriate feed change, process conditions are corresponding to realize
Other purposes, correlation change all without departing from the contents of the present invention, all similar substitutions and modifications are for this field skill
It is it will be apparent that being considered as being included within the scope of the present invention for art personnel.
Claims (5)
1. a kind of compound oxolinic acid with bactericidal activity is in application agriculturally, it is characterised in that: the compound is disliked
The structural formula of quinoline acid are as follows:
The compound is used for biocontrol of mango bacterial angular leaf spot, common bacterial blight of bean, soft rot of cabbage, rice bacterial leaf spot
Disease, citrus bacterial canker disease, blakleg of potato, rice basal stem rot, canker of pear and Prospect on Kiwifruit Bacterial Canker.
2. application according to claim 1, it is characterised in that: the oxolinic acid as active constituent and insecticides adjuvant,
Filler or solvent are configured to any one dosage form allowed on pesticide or the oxolinic acid compound and other agriculture chemical compounding cities
Any one dosage form allowed on pesticide.
3. application according to claim 2, it is characterised in that: the preferred suspending agent of the dosage form, wettable powder, moisture
Shot agent, granule, aqueous emulsion, microemulsion or ultra low volume liquids.
4. application according to claim 3, it is characterised in that: quality hundred of the compound oxolinic acid in above-mentioned dosage form
Divide than being 1-80%.
5. application according to any one of claims 1 to 4, it is characterised in that: the dosage of the compound oxolinic acid is
30-60g a.i./hm2。
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| CN116041166A (en) * | 2022-12-30 | 2023-05-02 | 华南理工大学 | 3, 6-diisoalkyl cyclohexanone-4, 5-dialkyl-1, 2-benzenediol, preparation method and application |
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Application publication date: 20190628 |