CN105669549A - Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof - Google Patents
Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof Download PDFInfo
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- -1 Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 17
- 230000000694 effects Effects 0.000 claims abstract description 9
- JUGUKRBVTSLIBR-UHFFFAOYSA-N acetic acid;1-ethylnaphthalene Chemical class CC(O)=O.C1=CC=C2C(CC)=CC=CC2=C1 JUGUKRBVTSLIBR-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 4
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract 1
- 230000033228 biological regulation Effects 0.000 abstract 1
- 235000012055 fruits and vegetables Nutrition 0.000 abstract 1
- 238000010899 nucleation Methods 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 238000005728 strengthening Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000035784 germination Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000000375 suspending agent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000004530 micro-emulsion Substances 0.000 description 5
- 238000002791 soaking Methods 0.000 description 5
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PUFFIFSUMICMHS-UHFFFAOYSA-N ClCC(=O)Cl.C1=CC=CC2=CC=CC=C12 Chemical compound ClCC(=O)Cl.C1=CC=CC2=CC=CC=C12 PUFFIFSUMICMHS-UHFFFAOYSA-N 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000000481 breast Anatomy 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 210000000582 semen Anatomy 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical group O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CCBICDLNWJRFPO-UHFFFAOYSA-N 2,6-dichloroindophenol Chemical compound C1=CC(O)=CC=C1N=C1C=C(Cl)C(=O)C(Cl)=C1 CCBICDLNWJRFPO-UHFFFAOYSA-N 0.000 description 1
- JHUFGBSGINLPOW-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)benzoyl cyanide Chemical compound FC(F)(F)OC1=CC=C(C(=O)C#N)C=C1Cl JHUFGBSGINLPOW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- QJZCOMPNBDPARF-AMSVHOKPSA-N O=C(Cc1cccc2ccccc12)OCCN(C(C(CC=C1)C=C1/C=C\C=C1)=O)C1=O Chemical compound O=C(Cc1cccc2ccccc12)OCCN(C(C(CC=C1)C=C1/C=C\C=C1)=O)C1=O QJZCOMPNBDPARF-AMSVHOKPSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 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
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012297 crystallization seed Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum 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
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses an Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound with the structure shown as the formula I and a purpose of the compound as a plant growth regulator. The compound shown as the formula I shown as the accompanying drawing has excellent plant growth regulation activity of promoting rooting, increasing the yield and improving the quality; by the modes of seed treatment or root and stem leaf spraying and the like, the compound can be widely applied to rooting, seeding strengthening, yield increase and quality improvement of plants or crops such as grains, cotton, fruit and vegetables, and has the characteristics of use safety, low cost, obvious effect and the like.
Description
Technical field
The invention belongs to plant growth regulator field in pesticide, be specifically related to a kind of aphthalimide base ethylnaphthalene acetate compounds and application thereof.
Background technology
Aphthalimide base ethylnaphthalene acetate compounds can be widely used for agricultural or production of forestry as plant growth regulator, has the features such as use cost low, good drug efficacy, use safety. Patent CN103641781B discloses the application as plant growth regulator of a kind of aphthalimide compounds and salt thereof, has and good inspires bud and the effect taken root, and increasing yield and improving quality or survival rate for farm-forestry crop improve. The invention provides a kind of structure such as aphthalimide base ethylnaphthalene acetate compounds shown in I and its production and use. This compound efficiently solves that the effect of increasing production of commercialization plant growth regulator is undesirable, the problem of degeneration-resistant weak effect, has good plant growth regulating activity, by soaking seed seed dressing or foliage-spray has significant growth-promoting root and production-increasing function. In the prior art, aphthalimide base ethylnaphthalene acetate compounds (compound of formula I) as described in the present invention and be applied in not disclosed both at home and abroad.
Summary of the invention
It is an object of the invention to provide one and prepare simplicity, aphthalimide base ethylnaphthalene acetate compounds easy to use, efficient, it is mainly used as plant growth regulator, promotes crop yield.
Aphthalimide base ethylnaphthalene acetate compounds I has excellent promoting cell elongation growth, induction and promote the effect of plant cell differentiation, and technical scheme is as follows:
The invention provides a kind of aphthalimide base ethylnaphthalene acetate compounds, structure shown in formula I:
Compound of formula I can be prepared by following reaction:
Naphthalene acetic acid reacts 2-3h in suitable solvent with thionyl chloride under 10 DEG C to reflux temperature, and decompression steams solvent and excessive thionyl chloride, prepares naphthalene chloroacetic chloride, prepared acyl chlorides adds suitable solvent solution-forming, temperature control-10 DEG C placement. Naphthalic anhydride and ethanolamine are heated to reflux to reacting completely obtaining Formula II compound in aqueous solvent. In the solution that-10 DEG C of stirring lower dropping naphthalene chloroacetic chlorides are made into Formula II compound and suitable solvent, add triethylamine and do acid binding agent, prepare compound of formula I.
The solvent that reaction is suitable for is selected from dichloromethane, toluene, ethyl acetate. Comparing with similar compound known on the market, the compound of formula I of the present invention has higher plant growth regulating activity, and its growth-promoting root performance and production-increasing function are significantly better than the plant growth regulators such as wide variety of " compound sodium nitrophenolate ", " Nafusaku ".The advantages such as the compound of formula I of the present invention has simple synthetic method, environmental protection, synthesis cost is low, effective dose is few. Therefore can realize reaching crops with relatively low use cost and prominent plant growth regulating activity significantly to increase production or forestry improves the purpose of survival rate.
Advantages of the present invention and good effect:
Commercial plant growth regulator is compared with compound of formula I, and compound of formula I has a higher effect promoting cell division differentiation, and its simple synthetic method, production cost are low; Compound I has the structure of aphthalimide and naphthalene acetic acid simultaneously, has both growth regulating-activities concurrently, and has good synergistic effect energy with other pesticide, fertilizer.
The compounds of this invention, when using as plant growth regulator, can be used alone, it is possible to uses with other active substance combination, to improve the combination property of product.
Present invention additionally comprises the compound of formula I plant growth regulator composition as active component, said composition includes compound of formula I as active component and agriculturally acceptable carrier.
The compositions of the present invention can use using the form of preparation: compound of formula I is dissolved or dispersed in as active component in carrier or solvent, adds appropriate surfactant and makes soluble powder, wettable powder, cream, microemulsion, aqueous emulsion, suspending agent etc.
It should be appreciated that, in the claim limited range of the present invention, various conversion and change can be carried out.
Detailed description of the invention
Following synthesis example, formulation examples and raw experimental result of surveying can be used to further illustrate the present invention, but are not intended to limit the present invention.
Synthesis example
Example 1, compound of formula I preparation
(1) preparation of naphthalene chloroacetic chloride
250mL there-necked flask is separately added into 18.6g (0.1mol) naphthalene acetic acid and 100mL toluene, the solution of dropping 17.9g (0.15mol) thionyl chloride and 30mL toluene composition, drip and finish, heating is to refluxing, stirring reaction 2h, rotation is evaporated off methylene chloride and thionyl chloride, obtains pale yellowish oil liquid 19.4g, productivity 94.6%.
(2) preparation of Formula II compound
250mL there-necked flask is separately added into 19.8g (0.1mol) naphthalic anhydride and 6.1g (0.1mol) ethanolamine, 100mL water as solvent, is heated to reflux, after reacting completely, the faint yellow crystalline solid of cooling sucking filtration, dry, obtain 23.4g, productivity 97.1%.
(3) preparation of compound of formula I
250mL there-necked flask is separately added into 24.1g (0.1mol) Formula II compound and 100mL ethyl acetate, it is simultaneously introduced 11.1g (0.11mol) triethylamine and makes acid binding agent, the solution that dropping 20.5g (0.1mol) naphthalene chloroacetic chloride forms with 30mL ethyl acetate, drip and finish, stirring reaction 2.5h under room temperature, be dissolved in water after having reacted triethylamine hydrochloride, and sucking filtration obtains light yellow solid (compound of formula I). White solid 30.7g, productivity 75.1%, fusing point 143.9 DEG C～148.3 DEG C is obtained with recrystallisation from isopropanol.
Compound of formula I1HNMR (500MHz, DMSO-d6), δ (ppm): 4.046 (s, 2H, CH2), 4.320-4.341 (t, 2H, CH2), 4.370-4.391 (t, 2H, CH2), 7.710-7.726 (d, 1H, Ar-H), 7.779-7.818 (t, 1H, Ar-H), 7.866-7.896 (t, 2H, Ar-H), 7.909-7.925 (d, 1H, Ar-H), 8.463-8.493 (t, 4H, Ar-H), 8.511-8.551 (q, 4H, Ar-H).
Formulation examples
The preparation of example 2,25% compound of formula I microemulsion
25g compound of formula I and 18g dimethylbenzene, 7g Ketohexamethylene, stirring and dissolving it is separately added in 250mL beaker, add 10gAEO-3 and 15g agriculture breast 600#, it is stirring evenly and then adding into 25g water, is sufficiently stirred for 0.5h, obtain 25% aphthalimide base ethylnaphthalene acetate compounds microemulsion.
The preparation of example 3,30% compound of formula I microemulsion
30g compound of formula I, 8g dimethylbenzene, 18g Ketohexamethylene, stirring and dissolving it is separately added in 250mL beaker, add 17g agriculture breast 1602 and 9g agriculture breast 601#, it is stirring evenly and then adding into 18g water, is sufficiently stirred for 0.5h, obtain 30% aphthalimide base ethylnaphthalene acetate compounds microemulsion.
The preparation of example 4,30% compound of formula I suspending agent
It is separately added into 30g compound of formula I in 250mL beaker, 5gNNO, 6gEL-60,11gMorwetD-425,2g aluminium-magnesium silicate, the xanthan gum solution of 10g0.1%, 5g ethylene glycol and 31g water, stir, proceed to and sand mill is fully ground 3h, obtain 30% aphthalimide base ethylnaphthalene acetate compounds suspending agent.
The preparation of example 5,45% compound of formula I wettable powder
Compound of formula I 45g, MorwetD-4256g, EL-403g, organobentonite 30g, Kaolin complements to 100g. 45% aphthalimide base ethylnaphthalene acetate compounds wettable powder.
The preparation of example 6,45% compound of formula I soluble powder
Compound of formula I 45g, sodium allylsulfonate 8g, Dispersant MF 9g, 600#5g, soluble starch complements to 100g. Obtain 40% aphthalimide base ethylnaphthalene acetate compounds soluble powder.
Biological activity determination
Example 7, Seeds Germination Tests
Paper bed sproutung method is adopted to carry out. respectively 30% compound of formula I suspending agent and DA-6 (Henan Zheng Shi Chemical Co., Ltd. product) are diluted to compound of formula I suspending agent and the 5%DA-6 water preparation of 5%, are diluted with distilled water into the plant growth regulator solution that concentration is 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL respectively. select Seed size uniform, full wheat seed, after seed being sterilized with hypochlorite solution, 8h is cultivated with the seed soaking of above-mentioned diluent in beaker, often process 100 seeds, repeat for 3 times, after process, seed is uniformly placed in the culture dish of double-layer filter paper, maintain a certain distance between seed, put it into 25 DEG C of insulation accelerating germination in full intelligence climate box after being well placed seed to process, period regularly to add distilled water makes filter paper keep moistening, the germination of each process is observed during accelerating germination, radicel length is about with the 1/2 of seed length for standard, wheat seed germination percentage in each culture dish is added up after 24h, compare with DA-6 and the clear water (CK) of same concentrations simultaneously, calculate each diluent germination promotion rate simultaneously, result is as shown in table 1 below.
Table 1 wheat seed germinating is tested
From table 1 experimental data, the wheat germination rate that formula I processes is better than contrast agents DA-6 on the whole, is more significantly better than clear water and processes the situation of (CK).
Example 8, seed soaking growth-promoting root experiment
Respectively compound of formula I 30% suspending agent and DA-6 (Henan Zheng Shi Chemical Co., Ltd. product) are diluted to compound of formula I suspending agent and the 5%DA-6 water preparation of 5%, are diluted with distilled water into the plant growth regulator solution that concentration is 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL respectively. Select the wheat seed that Seed size is uniform, full, after seed being sterilized with hypochlorite solution, 8h is cultivated with the seed soaking of above-mentioned diluent in beaker, often process 20 Semen Tritici aestivis, repeat for 3 times, after process, seed is uniformly placed on moistening paper bed, maintain a certain distance between seed, to ensure that seed fully absorbs moisture, when putting bed, embryo portion is upward towards the same side, putting it into after being well placed seed and carry out accelerating germination process 24h in full intelligence climate box, period regularly to add distilled water makes paper bed keep moistening.Treat that Semen Tritici aestivi main root exposes about 2mm, by its kind in the solid medium solidified, be then placed in full intelligence climate box and cultivate. With kind of calliper main root, stem height after 40h, and make detailed record. Processing (CK) with the DA-6 of same concentrations and clear water to compare, result is as shown in table 2 below simultaneously.
Table 2 wheat seed growth-promoting root is tested
By the result of table 2 it can be seen that the short rooting efficiency of Semen Tritici aestivi seed soaking is reached the best when 30 μ g/mL concentration by the compounds of this invention, hence it is evident that be better than comparison DA-6.
Example 9, field experiment
Fructus Mali pumilae experiment sets 3 process altogether, and each bough processing selection upper 3 growth potentials of new Gala apple tree suitable carries out, and experiment takes strain at random, tree-plot, repeats, respectively sprays once at red fuji apple young fruit period and fruit expanding period respectively for 3 times, foliage-spray clear water is as comparison, after results, measure the index of quality of Fructus Mali pumilae respectively, wherein, VC content adopts 2,6-Dichlorophenol indophenol method measures, and soluble sugar content adopts anthrone colorimetry to measure, and result is table 3 below such as.
Table 3 apple quality index experimental data
Above-mentioned aggregation of data analysis can be obtained, and the compound of formula I of the present invention has remarkable result in germination, growth-promoting root, and drug effect is substantially better than contrast agents (DA-6); After Fructus Mali pumilae is carried out foliage-spray, while improving apple production, improve outward appearance and the interior quality of Fructus Mali pumilae, it can be seen that the compound of the present invention is the plant growth regulator of a kind of excellent combination property.
Claims (4)
1. an aphthalimide base ethylnaphthalene acetate compounds, structure shown in formula I:
2. the purposes of aphthalimide base ethylnaphthalene acetate compounds according to claim 1, it is characterised in that compound of formula I is used as plant growth regulator.
3. aphthalimide base ethylnaphthalene acetate compounds according to claim 1 is as the using method of plant growth regulator: according to plant growing needs, adopt foliar spray, seed treatment, root to process, agent, soil treatment method is carried out, and working concentration is 0.1～1000 μ g/mL effective dose.
4. a plant growth regulator composition, containing the compound of formula I described in claim 1 as acceptable carrier in Activities of Plant Growth Regulators component and agricultural or forestry.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610102732.0A CN105669549B (en) | 2016-02-25 | 2016-02-25 | A kind of aphthalimide base ethylnaphthalene acetate compounds and its application |
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| CN201610102732.0A CN105669549B (en) | 2016-02-25 | 2016-02-25 | A kind of aphthalimide base ethylnaphthalene acetate compounds and its application |
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| Publication Number | Publication Date |
|---|---|
| CN105669549A true CN105669549A (en) | 2016-06-15 |
| CN105669549B CN105669549B (en) | 2019-04-19 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106800549A (en) * | 2017-01-10 | 2017-06-06 | 青岛科技大学 | A kind of imidazoles acid naphthalimide base ethyl ester compound and application thereof |
| CN106800534A (en) * | 2017-01-10 | 2017-06-06 | 青岛科技大学 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
| CN106831579A (en) * | 2017-01-10 | 2017-06-13 | 青岛科技大学 | A kind of methyl α-naphthyl acetate naphthalimide ester type compound and application thereof |
| CN106866505A (en) * | 2017-01-19 | 2017-06-20 | 青岛科技大学 | Acetylsalicylic acid esters plant growth regulator |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106800549A (en) * | 2017-01-10 | 2017-06-06 | 青岛科技大学 | A kind of imidazoles acid naphthalimide base ethyl ester compound and application thereof |
| CN106800534A (en) * | 2017-01-10 | 2017-06-06 | 青岛科技大学 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
| CN106831579A (en) * | 2017-01-10 | 2017-06-13 | 青岛科技大学 | A kind of methyl α-naphthyl acetate naphthalimide ester type compound and application thereof |
| CN106800534B (en) * | 2017-01-10 | 2019-06-18 | 青岛科技大学 | A kind of cinnamic acid naphthalimide ester type compound and application thereof |
| CN106866505A (en) * | 2017-01-19 | 2017-06-20 | 青岛科技大学 | Acetylsalicylic acid esters plant growth regulator |
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| Publication number | Publication date |
|---|---|
| CN105669549B (en) | 2019-04-19 |
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