CN106800534A - A kind of cinnamic acid naphthalimide ester type compound and application thereof - Google Patents
A kind of cinnamic acid naphthalimide ester type compound and application thereof Download PDFInfo
- Publication number
- CN106800534A CN106800534A CN201710018077.5A CN201710018077A CN106800534A CN 106800534 A CN106800534 A CN 106800534A CN 201710018077 A CN201710018077 A CN 201710018077A CN 106800534 A CN106800534 A CN 106800534A
- Authority
- CN
- China
- Prior art keywords
- formula
- compound
- plant growth
- cinnamic acid
- apple
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- -1 cinnamic acid naphthalimide ester Chemical class 0.000 title claims abstract description 10
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title claims abstract description 8
- 229930016911 cinnamic acid Natural products 0.000 title claims abstract description 8
- 235000013985 cinnamic acid Nutrition 0.000 title claims abstract description 8
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 241000209140 Triticum Species 0.000 claims abstract description 15
- 235000021307 Triticum Nutrition 0.000 claims abstract description 15
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 15
- 240000008067 Cucumis sativus Species 0.000 claims abstract description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims abstract description 7
- 241000233616 Phytophthora capsici Species 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 241000223218 Fusarium Species 0.000 claims abstract description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 6
- 206010039509 Scab Diseases 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 230000003641 microbiacidal effect Effects 0.000 claims 1
- 229940124561 microbicide Drugs 0.000 claims 1
- 239000002855 microbicide agent Substances 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 230000006806 disease prevention Effects 0.000 abstract description 2
- 244000141359 Malus pumila Species 0.000 description 12
- 235000011430 Malus pumila Nutrition 0.000 description 12
- 235000015103 Malus silvestris Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000000375 suspending agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 241000223195 Fusarium graminearum Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000000839 emulsion 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
- 238000002386 leaching Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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
- 241000213004 Alternaria solani Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241000555706 Botryosphaeria dothidea Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 241001290235 Ceratobasidium cereale Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- 241001115351 Physalospora 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
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- GANNOFFDYMSBSZ-UHFFFAOYSA-N [AlH3].[Mg] Chemical compound [AlH3].[Mg] GANNOFFDYMSBSZ-UHFFFAOYSA-N 0.000 description 1
- JUGUKRBVTSLIBR-UHFFFAOYSA-N acetic acid;1-ethylnaphthalene Chemical class CC(O)=O.C1=CC=C2C(CC)=CC=CC2=C1 JUGUKRBVTSLIBR-UHFFFAOYSA-N 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 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
- 210000000481 breast Anatomy 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000021393 food security Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- HCRRFKSGGHDXKQ-UHFFFAOYSA-N naphthalene;3-phenylprop-2-enoic acid Chemical compound C1=CC=CC2=CC=CC=C21.OC(=O)C=CC1=CC=CC=C1 HCRRFKSGGHDXKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007226 seed germination Effects 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
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a kind of structure cinnamic acid naphthalimide ester type compound shown in formula I, as plant growth regulator.Compound of formula I has and excellent inspire bud, takes root and increasing yield and improving quality is acted on, and with good bactericidal action, particularly there is preventive and therapeutic effect in 200ppm etc. to Phytophthora capsici disease, wheat scab, ring rot of apple, cucumber fusarium axysporum, disease prevention, the volume increase of agricultural or forestry is can be widely used for.
Description
Technical field is the invention belongs to plant growth regulator field in agricultural chemicals, and in particular to the formyl of cinnamic acid naphthalene two is sub-
Amine ester and application thereof.
Background technology plant growth regulator as the big classification in agricultural chemicals, in agricultural production and income, improve quality etc.
Aspect played an important role, and increasingly be attracted attention at aspects such as Ensuring Food Safety, food securities.Patent CN
103130663B discloses a kind of purposes of cinnamate derivative compound as plant growth regulator, patent CN
105481762B discloses a kind of purposes of cinnamic acid pyridine ethyl ester type compound as plant growth regulator.Patent CN
105669549A discloses a kind of aphthalimide base ethylnaphthalene acetate compounds and its as plant growth regulator
Purposes, patent CN 105669550A disclose a kind of aphthalimide base thylhexoic acid esters compound and its are given birth to as plant
The purposes of conditioning agent long.In the prior art, cinnamic acid naphthalimide ester (compound of formula I) as described in the present invention and its
Purposes is not disclosed at home and abroad.
The content of the invention is it is an object of the invention to provide a kind of cinnamic acid for having plant growth regulating activity and bactericidal activity concurrently
Naphthalimide ester type compound, promotes plant establishment germination, there is obvious effect of increasing production, production and application low cost and use peace
Entirely, can be used for the increasing yield and improving quality of crops and fruits and vegetables.
Technical scheme is as follows：
A kind of cinnamic acid naphthalimide ester plant growth regulator, structure is shown in formula I：
Compound of formula I can be obtained by following reaction：
Specific preparation method is shown in that this specification synthesizes example.
Formula I as plant growth regulator application：Compound of formula I has water-insoluble, using when
Emulsion, suspending agent, wettable powder etc. must be processed into, substance content is 1~80% in preparation, can be according to reality when using
Need that above-mentioned preparation is watered the suspension or aqueous emulsion that are diluted to 0.1~1000 μ g/mL concentration, carry out leaching root, root dipping, leaching
Kind, seed dressing, seed pelleting spray cauline leaf.
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 such as the plant such as sodium cinnamate, compound sodium nitrophenolate, indolebutyric acid sodium of other active components
The composition of a kind of, two or more compositions of thing growth regulator, also includes agricultural in the plant growth regulator composition
Or acceptable carrier in forestry.There is certain bactericidal activity present invention additionally comprises compound of formula I, as germicide constituent,
Can be used alone, it is also possible to carry out compounding use with other bactericide, to improve the comprehensive function of product.
Advantages and positive effects of the present invention：Indoor and field control effectiveness test shows that compound of formula I has notable to crop
Promotion growth, increasing yield and improving quality effect, have good for wheat, paddy rice, corn, potato, cucumber, tomato, capsicum, apple etc.
Good diseases prevention and volume increase double action.As respectively sprayed once in wheat tillering and heading stage under the μ g/mL concentration of compound of formula I 100,
Volume increase 18-20%；In rice tillering and heading stage, respectively sprinkling once, increases production 15-18%；In red fuji apple young fruit period and fruit
Expanding stage is respectively sprayed once, precocious one week, volume increase more than 20%, and coloring and mouthfeel are obviously improved.Meanwhile, compound of formula I pair
Agriculture Common fungi disease such as Phytophthora capsici disease, ring rot of apple, wheat scab, cucumber fusarium axysporum, the late blight of potato, water
Sheath and culm blight of rice etc. has preventive and therapeutic effect.Formula I prepares simple, production and use cost is low, not only disease prevention but also volume increase,
Production and use cost are low, and consumption is small, concentration wide ranges, safe and convenient to use, can be widely used for various crops and fruit
Promoting root growth, volume increase, degeneration-resistant, upgrading, anti-fungus damage of vegetable etc., are multifunctional plant growth regulators rare at present, with wide
Wealthy commercialization prospect and market potential.
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 preparation of example 1, compound of formula I
(1) preparation of cinnamoyl chloride
14.8g (0.1mol) cinnamic acid, 150mL toluene, 14.3g (0.12mol) are sequentially added in 250mL there-necked flasks
Thionyl chloride, is stirred at room temperature lower dropwise addition 0.2mL DMFs, temperature rising reflux 2h.TLC monitoring reactions are completed, revolving
Go out the thionyl chloride of solvent and excess, obtain 16.1g pale yellowish oil liquid, yield is 96.4%.
(2) preparation of Formula II compound
19.8g (0.1mol) naphthalic anhydrides and 8.34g (0.12mol) hydrochloric acid are separately added into 250mL there-necked flasks
Azanol, 4.8g (0.1mol) NaOH, 150mL water as solvent, heating stirring backflow, after TLC monitoring reactions completely, cooling is taken out
Orange red solid is filtered to obtain, is dried, obtain 20.7g, yield 97.1%.
(3) preparation of compound of formula I
21.3g (0.1mol) Formula II compounds and 150mL toluene are separately added into 250mL there-necked flasks, 20.0g is added dropwise
(0.12mol) cinnamoyl chloride and the solution of 30mL toluene composition, drip and finish, and are heated to reflux lower stirring reaction 4.5h, TCL detection reactions
After completely, suction filtration obtains chartreuse solid 23.4g, yield 71.0%, 180.1~212.3 DEG C of fusing point.
Compound of formula I1H NMR (500MHz, DMSO-d6), δ (ppm)：7.159-7.176 (d, 1H, CH), 7.486-
7.530 (q, 3H, Ar-H), 7.900-7.914 (d, 2H, Ar-H), 7.931-7.962 (t, 2H, Ar-H), 8.027-8.060 (d,
1H, CH), 8.571-8.593 (q, 4H, Ar-H).
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.
First, plant regulation activity test
Example 3, Seeds Germination Tests
Carried out using paper bed sproutung method.Respectively by 30% compound of formula I suspending agent and DA-6 (the Henan limited public affairs of Zheng Shi chemical industry
Department produces) 5% compound of formula I suspending agent and 5%DA-6 aquas are diluted to, concentration is diluted with distilled water into respectively for 10 μ g/
The plant growth regulator solution of mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL.Select Seed size uniform, full
Full wheat seed, after carrying out sterilization to seed with hypochlorite solution, is soaked seed with above-mentioned dilution in beaker and cultivates 8h, is often located
Uniformly be placed in the culture dish of double-layer filter paper seed after treatment by 100 seeds of reason, 3 repetitions, and one is kept between seed
Fixed distance, is well placed after seed and puts it into 25 DEG C of insulation vernalization treatment in full intelligence climate box, and period will regularly add
Distilled water makes filter paper keep moistening, observes the germination of each treatment during vernalization, radicel length about with seed it is long 1/2 be mark
Standard, the wheat seed germination percentage in each culture dish is counted after 24h, while compared with the DA-6 and clear water (CK) of same concentrations,
Each dilution germination promotion rate is calculated simultaneously, it is as a result as shown in table 1 below.
The wheat seed germinating of table 1 is tested
From the experimental data of table 1, the wheat germination rate of formula I treatment is better than contrast agents on the whole
DA-6, is more significantly better than the situation of clear water treatment (CK).
Example 4, the root experiment of seed soaking growth-promoting
The suspending agent of compound of formula I 30% and DA-6 (Henan Zheng Shi Chemical Co., Ltd.s product) are diluted to 5% respectively
Compound of formula I suspending agent and 5%DA-6 aquas, be diluted with distilled water into respectively concentration for 10 μ g/mL, 20 μ g/mL, 30 μ g/mL,
The plant growth regulator solution of 60 μ g/mL and 120 μ g/mL.Uniform, the full wheat seed of Seed size is selected, secondary chlorine is used
After acid solution carries out sterilization to seed, soaked seed with above-mentioned dilution in beaker and cultivate 8h, often 20 wheats for the treatment of, 3 repetitions,
Seed is uniformly placed on the paper of moistening bed after treatment, is maintained a certain distance between seed, to ensure that seed is fully absorbed
Moisture, embryo portion is well placed after seed to put it into and carry out vernalization in full intelligence climate box upward towards the same side when putting bed
Treatment 24h, period regularly to add distilled water make paper bed keep moistening.Treat that wheat main root exposes 2mm or so, by its kind
In the solid medium of solidification, it is then placed in being cultivated in full intelligence climate box.It is high with kind of calliper main root, stem after 40h, and
Make detailed record.Compared with the DA-6 of same concentrations and clear water treatment (CK) simultaneously, it is as a result as shown in table 2 below.
The wheat seed growth-promoting root of table 2 is tested
The compounds of this invention is can be seen that by the result of table 2 to reach wheat seed soaking rush rooting efficiency in 30 μ g/mL concentration
To optimal, hence it is evident that better than control DA-6.
To sum up data, it can be seen that compound of formula I of the invention has significantly effect at germination, seedling aspect of taking root
Really.
Example 5, 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 is respectively sprayed once, and foliage-spray clear water after results, measures the index of quality of apple respectively as control, wherein, VC contains
Amount uses 2,6- dichloropheno-lindophenols method to determine, and soluble sugar content is determined using anthrone colorimetry, as a result such as table 3 below.
The apple quality index Test data of table 3
After compound of formula I being can be seen that by the data of table 3 to apple foliage-spray so that the output increased 20.5% of apple,
The outward appearance and interior quality of apple are improved simultaneously, and VC and soluble sugar content are all significantly increased.
2nd, bactericidal activity experiment
Example 6, by a certain amount of medicament dissolution in appropriate DMF, be then diluted to 2000mg/L with emulsified water.Using in vitro
Plating, for examination pathogen：Rhizoctonia cerealis (Rhizotonia cerealis), fusarium graminearum (Fusarium
Graminearum), phytophthora infestans (Phytophthora infestans), cucumber fusarium axysporum (Fusarium
Oxysporum), tomato early blight bacterium (Alternaria solani), P. capsici (Phytophthora
Capsici), Botryosphaeria berengeriana f. sp (Physalospora piricola), Rhizoctonia solani Kuhn (Rhizoctonia
solani)。
Using biomass growth rate determination method (mycelium growth rate test), detailed process is：In aseptic bar
It is each under part to draw in 1mL liquids injection culture dish, 9mLPDA culture mediums are added, 200mg/L pastille flat boards are made after shaking up, to add
Plus the flat board of 1mL aqua sterilisas does blank.Bacterium disk is cut along mycelia outer rim with the card punch of diameter 4mm, pastille flat board is moved to
On, it is per treatment in triplicate.Culture dish is placed on culture in 24 ± 1 DEG C of constant incubators, the extension of bacterium disk is investigated after 72h straight
Footpath, averages.Bacteriostasis rate effect is listed in Table 4 below.
Preventive effect (%)=(blank colony diameter-treatment colony diameter)/(blank colony diameter -4) × 100%
Table 4 BA preventive effect (%) data
Compound of formula I is can be seen that to fusarium graminearum, Phytophthora capsici disease, cucumber fusarium axysporum, apple by the data of table 4
Fruit ring spot etc. has preventive and therapeutic effect, the purposes with control fungus damage.
Claims (4)
1. a kind of cinnamic acid naphthalimide ester type compound, structure is shown in formula I：
2. the purposes of compound of formula I according to claim 1, it is characterised in that compound of formula I is used as plant growth regulating
Agent or as preventing and treating Phytophthora capsici disease, wheat scab, ring rot of apple, cucumber fusarium axysporum bactericide.
3. a kind of plant growth regulator composition, containing the compound of formula I described in claim 1 as plant growth regulator
Active component and agricultural or forestry acceptable carrier.
4. a kind of preventing and treating Phytophthora capsici disease, wheat scab, ring rot of apple, the microbicide compositions of cucumber fusarium axysporum, contain
Compound of formula I described in claim 1 is used as fungicidal activity component and agricultural or forestry acceptable carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710018077.5A CN106800534B (en) | 2017-01-10 | 2017-01-10 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710018077.5A CN106800534B (en) | 2017-01-10 | 2017-01-10 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106800534A true CN106800534A (en) | 2017-06-06 |
| CN106800534B CN106800534B (en) | 2019-06-18 |
Family
ID=58985442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710018077.5A Active CN106800534B (en) | 2017-01-10 | 2017-01-10 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106800534B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866540A (en) * | 2017-01-10 | 2017-06-20 | 青岛科技大学 | A kind of imidazolinedione class plant growth regulator and its application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669549A (en) * | 2016-02-25 | 2016-06-15 | 青岛科技大学 | Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof |
| CN105669550A (en) * | 2016-02-25 | 2016-06-15 | 青岛科技大学 | Naphthalenedicarboxamide ethylhexoate type compound and application thereof |
-
2017
- 2017-01-10 CN CN201710018077.5A patent/CN106800534B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669549A (en) * | 2016-02-25 | 2016-06-15 | 青岛科技大学 | Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof |
| CN105669550A (en) * | 2016-02-25 | 2016-06-15 | 青岛科技大学 | Naphthalenedicarboxamide ethylhexoate type compound and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| 左晓斌等: "《教您如何识别假农药、假化肥、假种子》", 31 December 2012 * |
| 鞠光秀: "萘酰亚胺、吡啶、苯基脲类化合物的研制及应用研究", 《青岛科技大学博士学位论文》 * |
| 韩长日等: "《饲料添加剂生产与应用技术》", 31 December 2014 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866540A (en) * | 2017-01-10 | 2017-06-20 | 青岛科技大学 | A kind of imidazolinedione class plant growth regulator and its application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106800534B (en) | 2019-06-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103641781B (en) | Application of naphthalimide type compounds and salts thereof as plant growth regulators | |
| CN103172614B (en) | One class contains anthranilic diamides derivative of sulfone (sulphur) imines and its production and use | |
| CN101845029A (en) | 4-methyl-1,2,3-tiadiazoline-5-formic ether compounds and preparation method and application thereof | |
| CN104926724A (en) | Naphthalene-dicarboxamide-contained bisquaternary ammonium salt type 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 | |
| CN104926725B (en) | Naphthalimide arylurea compound and use thereof | |
| CN106800534B (en) | A kind of cinnamic acid naphthalimide ester type compound and application thereof | |
| CN110447647B (en) | Plant growth regulator and application thereof | |
| CN105669550B (en) | A kind of aphthalimide base thylhexoic acid esters compound and its application | |
| CN106866530A (en) | A kind of naphthalimide replaces 2,4 dichloro-cinnamic acid ethyl ester compounds and its application | |
| CN103636602B (en) | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators | |
| CN106800549A (en) | A kind of imidazoles acid naphthalimide base ethyl ester compound and application thereof | |
| CN106749254B (en) | A kind of adenine ethylnaphthalene acetate compounds and its purposes as plant growth regulator | |
| CN106831579A (en) | A kind of methyl α-naphthyl acetate naphthalimide ester type compound and application thereof | |
| CN101591307B (en) | Di(1,2,3-thiadiazole-5-formic acid) and preparation method and application thereof | |
| CN105646347A (en) | Naphthalimide aryl urea compound and application thereof | |
| CN104351179B (en) | The Ag-fungicidal Activity of 8-phenyl (isopropyl) coumarin | |
| CN106748979B (en) | A kind of 2,4,6- trichlorophenyl pyridine ethyl ether plant growth regulator | |
| CN106749205B (en) | A kind of pyridine ethoxy coumarin class plant growth regulator | |
| CN104496980A (en) | Novel thiazole heterocyclic compound as well as preparation method and application thereof | |
| CN106866540A (en) | A kind of imidazolinedione class plant growth regulator and its application | |
| CN110642859B (en) | Pyrimidine thiothiopurine compound and application thereof | |
| CN103214474A (en) | 5-methyl-1,2,3-thiadiazole derivatives containing 4,5-dihydrothiazole alcohol acid esters and preparation methods and application thereof | |
| CN106866505A (en) | Acetylsalicylic acid esters plant growth regulator |
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 |