CN106831494A - 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
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- CN106831494A CN106831494A CN201710148549.9A CN201710148549A CN106831494A CN 106831494 A CN106831494 A CN 106831494A CN 201710148549 A CN201710148549 A CN 201710148549A CN 106831494 A CN106831494 A CN 106831494A
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- mebenil
- carbamide compounds
- growth regulator
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- -1 hexichol carbamide compounds Chemical class 0.000 title claims abstract description 13
- OZOMQRBLCMDCEG-VIZOYTHASA-N 1-[(e)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(O1)=CC=C1\C=N\N1C(=O)NC(=O)C1 OZOMQRBLCMDCEG-VIZOYTHASA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 abstract description 12
- 230000032823 cell division Effects 0.000 abstract description 10
- 230000009471 action Effects 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000004083 survival effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 241000209140 Triticum Species 0.000 description 14
- 235000021307 Triticum Nutrition 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 235000011430 Malus pumila Nutrition 0.000 description 11
- 235000015103 Malus silvestris Nutrition 0.000 description 11
- 244000141359 Malus pumila Species 0.000 description 10
- 230000035784 germination Effects 0.000 description 10
- 235000013399 edible fruits Nutrition 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 229930192334 Auxin Natural products 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002363 auxin Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MRKGZSUOHWCQNB-UHFFFAOYSA-N 4-(1h-indol-2-yl)butanoic acid;sodium Chemical compound [Na].C1=CC=C2NC(CCCC(=O)O)=CC2=C1 MRKGZSUOHWCQNB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 0 C*(NC(c1ccccc1NC(Nc1ccccc1)=O)=O)N(C)C Chemical compound C*(NC(c1ccccc1NC(Nc1ccccc1)=O)=O)N(C)C 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N CN(C)CCCN Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005979 Forchlorfenuron Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical compound [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FFLJZFAEPPHUCU-UHFFFAOYSA-N benzene;thiophene Chemical compound C=1C=CSC=1.C1=CC=CC=C1 FFLJZFAEPPHUCU-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 230000005200 bud stage Effects 0.000 description 1
- 230000028446 budding cell bud growth Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- GPXLRLUVLMHHIK-UHFFFAOYSA-N forchlorfenuron Chemical compound C1=NC(Cl)=CC(NC(=O)NC=2C=CC=CC=2)=C1 GPXLRLUVLMHHIK-UHFFFAOYSA-N 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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 structure mebenil base hexichol carbamide compounds shown in formula I, as plant growth regulator.Compound of formula I has the double action for promoting cell division and cell elongation, inspires bud, takes root and increasing yield and improving quality effect with excellent, and the volume increase or survival rate that can be widely used for agricultural or forestry are improved.
Description
Technical field is the invention belongs to plant growth regulator field in agricultural chemicals, and in particular to a kind of mebenil base hexichol
Carbamide compounds and application thereof.
Background technology plant growth regulator played an important role at aspects such as agricultural production and income, improve qualities.
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 replace and its salt to be used as plant growth regulator, with promote seed sprouting, growth-promoting root,
Volume increase, degeneration-resistant, precocious, improve quality effect.The acardite (4-PU) of aryl urea compounds such as commercialization, forchlorfenuron, thiophene
Benzene is grand 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 content of the invention is it is an object of the invention to provide a kind of mebenil for having auxin activity and cytokine activity concurrently
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.
Present invention additionally comprises compound of formula I as the plant growth regulator composition of active component, lived in said composition
Property component refer to compound of formula I or compound of formula I with other active components such as Nafusaku, compound sodium nitrophenolate, indolebutyric acid sodium, tune pyrrole
The composition of a kind of, two or more compositions of the plant growth regulator such as urea, also wraps in the plant growth regulator composition
Include acceptable carrier in agricultural or forestry.
Advantages and positive effects of the present invention：
Indoor and field test shows that formula I has the double effects of auxin and the basic element of cell division, carefully
Intracellular growth and cell division act synergistically, can remarkably promote germination, take root, cell differentiation, increasing yield and improving quality.Cucumber cotyledons expand
Open experiment to show, 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 germination promotion rate 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, the plant growth regulator 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 one-level 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 individual 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,
With low production cost, free of contamination advantage, the compound low toxicity, biological degradability are good, safe and convenient to use, with 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.
Specific 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.
Synthesis 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 to do 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 is disappeared, and reaction is completed.Water
Reaction solution is washed, and carries out a point liquid.Dry, revolving removes solvent, obtains product II about 20.9g, and yield is 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, heating for dissolving, returned
Stream dehydration.When anhydrous abjection, cooling down starts that the phenyl isocyanate of excessive (0.13mol) is added dropwise.About 20 minutes left sides of reaction
The right side, has a large amount of solids to occur, and reacts about 1h, and TLC is followed the trail of, and reaction is completed.Suction filtration obtains solid, dries, and obtains product I about 31.2g, 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 the sodium lignin sulfonates, (Malaysias of 3g polycarboxylate salt dispersant Sokalan CP 5 are weighed respectively
Acid-acrylic acid sodium salt), 1g organosilicons breast defoamer (the aqueous silicon emulsified antifoam agents of THIX-108), 2g aluminium-magnesium silicates and 5g second two
Alcohol adds 77g water in 250mL beakers, stirs, 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 regulation activity test
Example 3, cucumber cotyledons augmentation test
For examination cucumber variety to grind No. 4 in Tianjin, sowed after seed soaking in the enamel tray with cover for filling 0.7% agar, be placed in 26
72h is cultivated under DEG C dark situation, selected consistent cotyledon uniform in size is stand-by, sample preparation uses phytohormone activity substance-measuring
In filter paper enzyme, sampling test concentration be 100,10 μ g/mL, solvent is DMF.
Specific practice is：Type I compound and acardite (4-PU) are prepared as 1000,100 μ g/mL mother liquors, then are taken respectively
Each mother liquor 0.3mL is uniformly dripped on the filter paper of Φ 6cm, after solvent is air-dried, in the culture dish of Φ 6cm, is respectively put into containing sample
The filter paper of product 1, adds distilled water 3mL, cotyledon 10, as 100,10 μ g/mL treatment.It is control with distilled water.It is placed in
26 DEG C, cultivated under 3000Lux light intensity environment, every 10 slice, thin piece leaf fresh weight is measured after 72h.2 repetitions are often processed, is as a result averaged
Value, result of the test is shown in Table 1.
The cucumber cotyledons of table 1 expand contrast test
Show that type I compound of the present invention has preferable cytokine activity, better than known by the result of the test of table 1
The acardite basic element of cell division.
Example 4, wheat seed germinating is tested
Compound of formula I is prepared into suspending agent by the method for example 2 respectively, then with DA-6 (Henan Zheng Shi Chemical Co., Ltd.s
Produce) aqua and clear water compare.Concentration is diluted with distilled water into respectively for 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 125 μ
The plant growth regulator solution of g/mL.By wheat seed with above-mentioned dilution culture 8h, 100 seeds are processed, by seed point
For 3 parts (every part 30-40) are placed in the culture dish of double-layer filter paper, 25 DEG C of insulation vernalization, and keep filter paper to moisten, vernalization
The germination of each treatment of middle observation, radicel length about with seed it is long 1/2 as standard, the wheat hair in each ware is counted after 24h
Bud rate, while compared with the DA-6 and clear water (Ck) of same concentrations, 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 treatment (Ck) is significantly better than, illustrates that it has the effect of stratification.
The wheat germination test data of table 2
Example 5, the root experiment of seed soaking growth-promoting
The suspending agent of compound of formula I 5% and DA-6 aquas are diluted with distilled water into concentration for 12.5 μ g/ respectively respectively
The plant growth regulator solution of mL, 25 μ g/mL, 50 μ g/mL and 125 μ g/mL.Select uniform, the full wheat of Seed size
Seed, after carrying out sterilization to seed with hypochlorite solution, is put it into gauze, and 8h is soaked with above-mentioned dilution in beaker,
Then by wheat seed uniform discharge on the paper bed of moistening, when putting bed embryo portion upward towards germination box the same side, seed
Between to have a certain distance, to ensure that seed fully absorbs moisture, 20 wheats are put in each treatment, and being well placed after seed will
It is put into full intelligence weather vegetation box carries out germination treatment 24h, and period will regularly add the distilled water paper bed is kept moistening.Treat
Wheat main root exposes 2mm or so, and by its kind in the solid medium for having solidified, each treatment counterpoise is multiple 3 times, 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.Simultaneously with identical dense
The DA-6 and clear water (Ck) of degree are compared, and are as a result listed in the table below 3.
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 too high situation at stem aspect high, and
Not resistant to lodging, resultant effect is better than comparison medicament DA-6.
Example 6, wheat field test
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 three areas of same Parcel division, per 1 mu of area, each 1 mu of compound of formula I, blank.In wheat tillering and
Heading stage, is each once with carrying over-shoulder sprayer artificial spray, the μ g/mL of concentration 100, and every mu of each consumption is 15 kg of water, and does not apply
Compared with blank group.As a result：Administration group appearance is for 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 treatment are set altogether to apple experiment, each treatment new upper 3 life of Gala apple tree of selection
Suitable bough is carried out growing way, 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 results, measures the product of apple respectively as control
Matter index, wherein, VC contents use 2,6- dichloropheno-lindophenols method to determine, and soluble sugar content is determined using anthrone colorimetry, knot
Fruit such as table 4 below.
The apple quality index Test data of table 4
Be can be seen that after compound of formula I carries out foliage-spray to apple by the data of table 4, it is right while improving apple production
The outward 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 for the treatment of 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 used as control.Investigation individual plant is beared fruit number, fruit total output and rate of growth, results averaged.Result of the test is listed in table 5.
The tomato test data of table 5
Be can be seen that after compound of formula I carries out foliage-spray to tomato by the data of table 5, significantly improve individual 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. according to a kind of purposes of the mebenil base hexichol carbamide compounds described in claim 1, it is characterised in that compound of formula I
As plant growth regulator.
3. a kind of plant growth regulator composition, containing the compound of Formula I described in claim 1 as active component and agriculture
Acceptable carrier in industry or in forestry.
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| 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 |
| WO2021185391A1 (en) * | 2020-03-16 | 2021-09-23 | Univerzita Palackeho V Olomouci | Inhibitors of cytokinin oxidase derived from 1-[2-(hydroxyalkyl)phenyl]-3-ylurea, use thereof and preparations containing these derivatives |
| WO2021185390A1 (en) * | 2020-03-16 | 2021-09-23 | Univerzita Palackeho V Olomouci | Inhibitors of cytokinin oxidase derived from 2-(3-phenylureido)benzamide, use thereof and preparations containing these derivatives |
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| GB2604341A (en) * | 2021-02-26 | 2022-09-07 | Levity Crop Science Ltd | Agricultural composition for enhanced silicon uptake and distribution in plants |
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| CN108623531A (en) * | 2018-06-14 | 2018-10-09 | 青岛科技大学 | A kind of anthranilamide-based plant growth regulator |
| WO2021185391A1 (en) * | 2020-03-16 | 2021-09-23 | Univerzita Palackeho V Olomouci | Inhibitors of cytokinin oxidase derived from 1-[2-(hydroxyalkyl)phenyl]-3-ylurea, use thereof and preparations containing these derivatives |
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