CN106831494B - A kind of mebenil base hexichol carbamide compounds and application thereof - Google Patents
A kind of mebenil base hexichol carbamide compounds and application thereof Download PDFInfo
- Publication number
- CN106831494B CN106831494B CN201710148549.9A CN201710148549A CN106831494B CN 106831494 B CN106831494 B CN 106831494B CN 201710148549 A CN201710148549 A CN 201710148549A CN 106831494 B CN106831494 B CN 106831494B
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- mebenil
- carbamide compounds
- growth regulator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
Landscapes
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of a kind of mebenil base hexichol carbamide compounds of structure shown in formula I, as plant growth regulator.Compound of formula I has the double action for promoting cell division and cell elongation, have it is excellent inspire bud, take root and increasing yield and improving quality effect, can be widely used for agricultural or the volume increase of forestry or survival rate improve.
Description
The invention belongs to plant growth regulator field in pesticide for technical field, and in particular to a kind of mebenil base hexichol
Carbamide compounds and application thereof.
Background technology plant growth regulator played an important role in agricultural production and income, raising quality etc..
Auxin is the elongation growth for promoting cell, on cell division without influence.Patent ZL 201310729318.9, ZL
201310730571.6th, ZL 201310730613.6, ZL 201310732463.2 and ZL 201310732348.5 are disclosed and contained
There is amides compound that N- alkylaminos substitute and its salt to be used as plant growth regulator, have promotion seed sprouting, growth-promoting root,
Volume increase, effect that is degeneration-resistant, precocious, improving quality.Acardite (4-PU), forchlorfenuron, the thiophene of aryl urea compounds such as commercialization
Benzene is grand to be used as the basic element of cell division, and the physiological action of the basic element of cell division is to cause cell division, the formation of induced bud and promotes bud
Growth.In the prior art, mebenil base hexichol carbamide compounds as described in the present invention and its activity are at home and abroad showed no
It is open.
The object of the present invention is to provide a kind of mebenil for having auxin activity and cytokine activity concurrently for the content of the invention
Base hexichol carbamide compounds, it can be used for the increasing of crops as the plant growth regulator of promotion cell division and cell elongation
Produce upgrading.
Technical scheme is as follows：
A kind of mebenil base hexichol carbamide compounds, structure is shown in formula I：
Compound of formula I can be prepared by following reaction equation：
The preparation method of compound of formula I is shown in present invention synthesis example.
It is living in said composition present invention additionally comprises plant growth regulator composition of the compound of formula I as active component
Property component refer to compound of formula I or compound of formula I and other active components such as Nafusaku, compound sodium nitrophenolate, indolebutyric acid sodium, adjust pyrrole
The composition of a kind of, two or more compositions of the plant growth regulator such as urea, is also wrapped in the plant growth regulator composition
Include acceptable carrier in agricultural or forestry.
The advantages and positive effects of the present invention：
Indoor and field trial shows that formula Compound I has the double effects of auxin and the basic element of cell division, carefully
Intracellular growth acts synergistically with cell division, can remarkably promote germination, take root, cell differentiation, increasing yield and improving quality.Cucumber cotyledons expand
Open experiment and show that compound of formula I cytokine activity is better than the known acardite basic element of cell division (see example 3, table 1).Can
Significantly improve wheat germination rate, its promotion rate of germinateing is much higher than DA-6 up to 32.6% (see example 4, table 2)；In growth-promoting root side
Face is substantially better than DA-6 (see example 5, table 3).Field experiment shows, which can make that wheat cane is sturdy, leaf
Color is dark green, improves drought resisting, waterlogging-resistant ability, increases production 17% (see example 6).Accelerate apple with ripe color, improve apple in soluble sugar and
VC contents, make mouthfeel more sweet, expand Apple, improve level-one fruit rate, and prevent shedding, and volume increase nearly 25% is (see reality
Example 7, table 4).After compound of formula I carries out foliage-spray to tomato, improve single plant and bear fruit number and tomato yield, fruit shape just, it is thick
It is real, it is in good taste, increase production nearly 25% (see example 8, table 5).Compound of formula I raw material sources are wide, and synthesis is simple, no coupling product generation,
Have the advantages that production cost is low, free of contamination, compound low toxicity, biological degradability are good, safe and convenient to use, have very high
Application value and commercialization potentiality.
It should be clear that in scope defined by the claims of the present invention, various conversion and change can be carried out.
Embodiment
Following synthesis example, formulation examples and raw experimental result of surveying can be used to further illustrate the present invention, but not mean that
The limitation present invention.
Synthesize example
The synthesis of example 1, type I compound：
(1) preparation of Formula II compound：
Take 0.1mol (16.31g) isatoic anhydride to be placed in the there-necked flask of 250mL, and add 100mL ethyl acetate do it is molten
Agent.Lower dropwise addition 0.12mol (7.41g) propane diamine is stirred at room temperature, about 1h, is followed the trail of with TLC, and isatoic anhydride disappears, and reaction is completed.Water
Reaction solution is washed, and carries out liquid separation.Dry, revolving removes solvent, obtains product II about 20.9g, yield 96%.
(2) preparation of compound of formula I：
The Formula II compound of above-mentioned preparation is added in the 250mL there-necked flasks equipped with 100mL toluene, is dissolved by heating, is returned
Stream dehydration.To during anhydrous abjection, cooling down, starts that the phenyl isocyanate of excessive (0.13mol) is added dropwise.React about 20 minutes left sides
The right side, has a large amount of solids to occur, and reacts about 1h, TLC trackings, and reaction is completed.Solid is filtered to obtain, it is dry, product I about 31.2g are obtained, always
Yield is 92.9%.Formula II melting point compound：138.9-142.6℃.
1H NMR (500MHz, DMSO), δ/ppm：1.653-1.709(m,2H,CH2),2.135(s,6H,CH3),
2.261-2.296(m,2H,CH2),3.282-3.308(t,2H,CH2),6.938-6.967(t,1H,ArH),7.020-7.050
(t,1H,ArH),7.243-7.275(t,2H,ArH),7.410-7.441(t,1H,ArH),7.498-7.514(d,1H,ArH),
7.608-7.624(d,1H,ArH),8.202-8.219(d,1H,ArH),8.716-8.737(t,1H,NH),9.679(s,1H,
NH),10.285(s,1H,NH).
Example of formulations
The preparation of example 2,10% compound of formula I suspending agent：
10g compound of formula I, 2g sodium lignin sulfonates, 5 (Malaysias of 3g polycarboxylate salt dispersant Sokalan CP are weighed respectively
Acid-acrylic acid sodium salt), 1g organosilicon breasts defoamer (the water-based silicon emulsified antifoam agents of THIX-108), 2g aluminium-magnesium silicates and 5g second two
Alcohol adds 77g water, stirs evenly in 250mL beakers, and 2h is ground with sand mill, and rotating speed is 3000 revs/min, and detection granularity 3~
5 μm, obtain white mobility suspending agent.
It is raw to survey embodiment
First, plant adjusts activity test
Example 3, cucumber cotyledons augmentation test
No. 4 are ground for Tianjin for examination cucumber variety, is sowed after seed soaking in the enamel tray with cover of 0.7% agar is filled, is placed in 26
72h is cultivated under DEG C dark situation, selected consistent cotyledon uniform in size is stand-by, and sample preparation uses phytohormone activity substance-measuring
In filter paper enzyme, sampling test concentration is 100,10 μ g/mL, solvent DMF.
Specific practice is：Type I compound and acardite (4-PU) are prepared as 1000,100 μ g/mL mother liquors, then taken respectively
Uniformly drop on the filter paper of Φ 6cm, after solvent air-dries, in the culture dish of Φ 6cm, is respectively put into containing sample each mother liquor 0.3mL
The filter paper 1 of product is opened, and adds distilled water 3mL, cotyledon 10, is 100,10 μ g/mL processing.Using distilled water as control.It is placed in
26 DEG C, cultivate under 3000Lux light intensity environment, every 10 slice, thin piece leaf fresh weight is measured after 72h.2 repetitions are often handled, are as a result averaged
Value, result of the test are shown in Table 1.
1 cucumber cotyledons of table expand contrast test
Shown by 1 result of the test of table, type I compound of the present invention has preferable cytokine activity, better than known
The acardite basic element of cell division.
Example 4, wheat seed germinating experiment
Compound of formula I is prepared into suspending agent by 2 method of example respectively, then with DA-6 (Henan Zheng Shi Chemical Co., Ltd.s
Produce) aqua and clear water compare.It is 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 125 μ to be diluted with distilled water into concentration respectively
The plant growth regulator solution of g/mL.By wheat seed above-mentioned dilution culture 8h, 100 seeds of processing, by seed point
It is placed on for 3 parts (every part 30-40) in the culture dish of double-layer filter paper, 25 DEG C of insulation vernalization, and keeps filter paper to moisten, vernalization
The germination of middle each processing of observation, radicel length are standard about with the 1/2 of seed length, and wheat in each ware is counted after 24h and is sent out
Bud rate, while compared with the DA-6 of same concentrations and clear water (Ck), while each dilution germination promotion rate is calculated, it is as a result as follows
Shown in table 2.
As can be seen from Table 2, compound of formula I of the invention is in 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL concentration,
Its germination percentage is better than DA-6 comparison medicaments, increases with concentration, inhibition occurs, and low concentration uses more preferable.Its overall germination percentage
The situation of clear water processing (Ck) is significantly better than, illustrates its effect with stratification.
2 wheat germination test data of table
Example 5, the root experiment of seed soaking growth-promoting
It is 12.5 μ g/ that the suspending agent of compound of formula I 5% and DA-6 aquas are diluted with distilled water into concentration respectively respectively
ML, 25 μ g/mL, the plant growth regulator solution of 50 μ g/mL and 125 μ g/mL.Select the wheat that Seed size is uniform, full
Seed, after being sterilized with hypochlorite solution to seed, puts it into gauze, soaks 8h with above-mentioned dilution in beaker,
Then by wheat seed uniform discharge on the paper bed of moistening, embryo portion is upward towards the same side of germination box, seed when putting bed
Between to have a certain distance, to ensure that seed fully absorbs moisture, 20 wheats are put in each processing, and being well placed after seed will
It is put into complete intelligent weather vegetation box and carries out germination treatment 24h, and during which periodically to add distilled water makes paper bed keep moistening.Treat
Wheat main root exposes 2mm or so, and by its kind in the solid medium solidified, each counterpoise that handles is 3 times multiple, is then placed in complete
Cultivated in intelligent weather vegetation box.It is high with kind of calliper main root, stem after 40h, and make detailed record.At the same time with identical dense
The DA-6 and clear water (Ck) of degree are compared, and the results are shown in table 3 below.
The seed soaking Rooting data of table 3
As can be seen from Table 3, compound of formula I can promote the growth of root, and taproot and lateral root is longer than comparison medicament DA-6,
Better than clear water, illustrates that it can act on well developed root system, beneficial to wheat growth.Be not in excessive situation in terms of stem height, and
Not resistant to lodging, resultant effect is better than comparison medicament DA-6.
Example 6, wheat field trial
Test site：Qingdao of Shandong province Pingdu Cui Jia market towns Zhang Jiafang villages.Time：The 3-6 months in 2016.Object：Spring is small
Wheat.Test method：In same three areas of Parcel division, per 1 mu of area, each 1 mu of compound of formula I, blank control.In wheat tillering and
Heading stage, is manually sprayed respectively once with carrying over-shoulder sprayer, and 100 μ g/mL of concentration, each dosage is 15 kg of water per acre, with not applying
Compared with blank group.As a result：Administration group appearance is that cane is sturdy, leaf color is dark green, full grains.Blank per mu yield 550 is public
Jin, using 645 kilograms of compound of formula I per mu yield, volume increase 17.3%.
Example 7, field experiment：3 processing are set altogether to apple experiment, each processing selects new upper 3 lifes of Gala apple tree
The suitable bough of growing way carries out, and experiment takes strain, tree-plot, 3 repetitions, respectively in red fuji apple young fruit period and fruit at random
Expanding stage respectively sprays once (concentration is 100 μ g/mL), and foliage-spray clear water after harvest, measures the product of apple respectively as compareing
Matter index, wherein, VC contents are measured using 2,6- dichloropheno-lindophenols method, and soluble sugar content is measured using anthrone colorimetry, knot
Fruit such as table 4 below.
4 apple quality index Test data of table
It is right while improving apple production after compound of formula I it can be seen from 4 data of table carries out foliage-spray to apple
The appearance and interior quality of apple are also significantly improved, it can be seen that compound of the invention is a kind of plant of excellent combination property
Thing growth regulator.
Example 8, field experiment：Uniform 30 plants of the tomato of growing way is chosen in experiment, is respectively sprayed once in seedling stage, bud stage, 3
The concentration of processing is 20 μ g/mL, 50 μ g/mL, 100 μ g/mL respectively spray 10 plants, and interval time is 10 days, selects 10 plants of foliage-sprays
Clear water is as control.Investigation single plant is beared fruit number, fruit total output and rate of growth, and results are averaged.Result of the test is listed in table 5.
5 tomato test data of table
By compound of formula I it can be seen from 5 data of table to tomato carry out foliage-spray after, significantly improve single plant bear fruit number and
Tomato yield.
Claims (3)
1. a kind of mebenil base hexichol carbamide compounds, structure is shown in formula I：
2. the purposes of a kind of mebenil base hexichol carbamide compounds described in claim 1, it is characterised in that compound of formula I is used as
Plant growth regulator.
3. a kind of plant growth regulator composition, contains the compound of formula I described in claim 1 as active component and agricultural
Acceptable carrier in upper or forestry.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710148549.9A CN106831494B (en) | 2017-03-14 | 2017-03-14 | A kind of mebenil base hexichol carbamide compounds and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710148549.9A CN106831494B (en) | 2017-03-14 | 2017-03-14 | A kind of mebenil base hexichol carbamide compounds and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106831494A CN106831494A (en) | 2017-06-13 |
| CN106831494B true CN106831494B (en) | 2018-04-17 |
Family
ID=59143580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710148549.9A Active CN106831494B (en) | 2017-03-14 | 2017-03-14 | A kind of mebenil base hexichol carbamide compounds and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106831494B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022180396A1 (en) * | 2021-02-26 | 2022-09-01 | Levity Crop Science Limited | Agricultural composition for enhanced silicon uptake and distribution in plants |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107892598A (en) * | 2017-11-07 | 2018-04-10 | 王庆贤 | A kind of plant establishment auxiliary agent |
| CN108623531A (en) * | 2018-06-14 | 2018-10-09 | 青岛科技大学 | A kind of anthranilamide-based plant growth regulator |
| CZ2020143A3 (en) * | 2020-03-16 | 2021-09-29 | Univerzita Palackého v Olomouci | Cytokinin oxidase inhibitors based on 2- (3-phenyl-ureido) -benzamide derivatives, preparations containing them and their use |
| CZ2020144A3 (en) * | 2020-03-16 | 2021-09-29 | Univerzita Palackého v Olomouci | Cytokinin oxidase inhibitors based on 1- [2- (hydroxy-alkyl) -phenyl] -3-yl-urea derivatives, preparations containing them and their use |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001032604A1 (en) * | 1999-11-05 | 2001-05-10 | University College London | Activators of soluble guanylate cyclase |
| WO2004048319A1 (en) * | 2002-11-25 | 2004-06-10 | 7Tm Pharma A/S | Novel benzamide compounds for use in mch receptor related disorders |
| CN103636602A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators |
-
2017
- 2017-03-14 CN CN201710148549.9A patent/CN106831494B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001032604A1 (en) * | 1999-11-05 | 2001-05-10 | University College London | Activators of soluble guanylate cyclase |
| WO2004048319A1 (en) * | 2002-11-25 | 2004-06-10 | 7Tm Pharma A/S | Novel benzamide compounds for use in mch receptor related disorders |
| CN103636602A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators |
Non-Patent Citations (1)
| Title |
|---|
| 新型植物生长调节剂的合成及生物活性测试;孟祥龙;《万方论文数据库》;20150907;全文 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022180396A1 (en) * | 2021-02-26 | 2022-09-01 | Levity Crop Science Limited | Agricultural composition for enhanced silicon uptake and distribution in plants |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106831494A (en) | 2017-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106831494B (en) | A kind of mebenil base hexichol carbamide compounds and application thereof | |
| CN103641781B (en) | Application of naphthalimide type compounds and salts thereof as plant growth regulators | |
| CN105777381B (en) | Vitamin B-containing medium-trace element compound fertilizer and preparation method thereof | |
| CN104926724A (en) | Naphthalene-dicarboxamide-contained bisquaternary ammonium salt type plant growth regulator | |
| CN106613832A (en) | Culture method of dendrobium officinale | |
| CN109907060B (en) | Plant growth regulating composition containing chlorin iron and application thereof as plant growth regulator | |
| CN105669549B (en) | A kind of aphthalimide base ethylnaphthalene acetate compounds and its application | |
| CN104920448B (en) | Naphthalimide potassium phosphate plant growth regulator and application thereof | |
| CN110447647B (en) | Plant growth regulator and application thereof | |
| RU2370957C1 (en) | Preparation "bios" - stimulator of plants growing and developing | |
| CN103724265B (en) | Naphthalenedicarboxamide-containing compound and preparation method thereof as well as plant growth regulator composition comprising same | |
| CN103636602B (en) | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators | |
| WO2023115742A1 (en) | Brassinosteroid analog, new crystal form, preparation method, and use | |
| CN110436996A (en) | A kind of compound botanical growth composition and preparation method thereof | |
| CN116267384A (en) | Method for promoting transplanted papaya seedlings to root rapidly | |
| CN105669550B (en) | A kind of aphthalimide base thylhexoic acid esters compound and its application | |
| CN103694128B (en) | A kind of Beet alkaline plant growth regulator containing sorb amide group | |
| CN106749254B (en) | A kind of adenine ethylnaphthalene acetate compounds and its purposes as plant growth regulator | |
| CN106748979B (en) | A kind of 2,4,6- trichlorophenyl pyridine ethyl ether plant growth regulator | |
| JP6842082B2 (en) | Plant growth regulator | |
| CN103694129B (en) | Beet alkaline plant growth regulator containing cinnamamide groups | |
| PL225459B1 (en) | Method for propagation of shadbush plants (Amelanchier alnifolia Nutt.) | |
| CN106866540A (en) | A kind of imidazolinedione class plant growth regulator and its application | |
| CN106749205B (en) | A kind of pyridine ethoxy coumarin class plant growth regulator | |
| CN105646348B (en) | A kind of aphthalimide base α-naphthoacetyl isothiocyanate class compound and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230506 Address after: 274000 South Chemical Industry Park, Dongming County, Heze City, Shandong Province Patentee after: Heze Dior Chemical Co.,Ltd. Address before: No. 53, Zhengzhou Road, North District, Qingdao, Shandong Patentee before: QINGDAO University OF SCIENCE AND TECHNOLOGY |