CN106749254B - A kind of adenine ethylnaphthalene acetate compounds and its purposes as plant growth regulator - Google Patents
A kind of adenine ethylnaphthalene acetate compounds and its purposes as plant growth regulator Download PDFInfo
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- CN106749254B CN106749254B CN201710018178.2A CN201710018178A CN106749254B CN 106749254 B CN106749254 B CN 106749254B CN 201710018178 A CN201710018178 A CN 201710018178A CN 106749254 B CN106749254 B CN 106749254B
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- Prior art keywords
- plant growth
- formula
- growth regulator
- compound
- ethylnaphthalene
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- KELGBDWVHRUFHJ-UHFFFAOYSA-N O=C(Cc1c(cccc2)c2ccc1)/[O]=C/CNc1c2nc[nH]c2nc[n-]1 Chemical compound O=C(Cc1c(cccc2)c2ccc1)/[O]=C/CNc1c2nc[nH]c2nc[n-]1 KELGBDWVHRUFHJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Abstract
The invention discloses a kind of 6 adenine phosphate ethylnaphthalene acetate compounds of structure shown in formula I, as plant growth regulator.Compound of formula I have it is excellent inspire bud, take root and increasing yield and improving quality effect, can be widely used for the volume increase of agricultural or forestry or survival rate raising.
Description
Technical field
The invention belongs to plant growth regulator fields in pesticide, and in particular to a kind of adenine ethylnaphthalene acetic acid esters
Class compound and its purposes as plant growth regulator.
Background technology
Plant growth regulator promotes cell elongation and division in control seed germination and dormancy, hestening rooting, controls side
Bud or tiller control plant type, and control is bloomed, and induce s.m.p fruit, and flower and fruit thinning controls shedding, controls fruit shape or maturity period, increases
Strong resistance (disease-resistant, drought resisting, salt resistance divide, are freeze proof), have additional nutrients ingredient, improves fruit color and luster and mouthfeel, and enhancing absorbs fertilizer
Ability etc. plays positive effect.
α-naphthylacetic acid methyl esters is a kind of plant growth regulator with auxin activity, be mainly used for potato bud inhibition,
Wheat suckering, beet storage, fruit bear fruit, inhibit tobacco lateral bud growth etc..Purine compound, such as 6-nonylaminopurine
(also known as kinetin, structural formula 1), zeatin (structural formula 2), 6- isopentene groups adenine phosphate (structural formula 3), 6- benzylaminos are fast
Purine (6-BA, structural formula 4) etc. has cell division activity, can promote plant cell growth, inhibit the degradation of plant chlorophyll, carry
The content of homoamino acid, Delaying Leaf-Senescence, the differentiation of induced bud promote lateral bud growth, promote cell division, moreover it is possible to reduce and plant
The decomposition of object inner chlorophyll has and delays and inhibit plant senescence, protects green effect.
In the prior art, a kind of adenine ethylnaphthalene acetate compounds and its conduct as described in the present invention
The purposes of plant growth regulator is not disclosed.
The content of the invention
It is an object of the invention to provide a kind of promotion seed sproutings, growth-promoting root, volume increase, it is safe to use, have sterilization work concurrently
Plant growth regulator is specifically to provide a kind of adenine ethylnaphthalene acetate esters plant growth regulator,
It can be used for the significantly volume increase and upgrading of crops and water fruits and vegetables.
Technical scheme is as follows：
The present invention provides a kind of adenine ethylnaphthalene acetate esters plant growth regulator for having bactericidal effect concurrently,
Its structure is shown in formula I：
Compound of formula I can be made by following reaction, and specific preparation method is shown in present invention synthesis example.
It is living in said composition present invention additionally comprises plant growth regulator composition of the compound of formula I as active component
Property component refer to compound of formula I or compound of formula I and given birth to other active components such as plants such as Nafusaku, DA-6, indolebutyric acid sodium
The composition of a kind of, two or more compositions of long conditioning agent further includes agricultural or woods in the plant growth regulator composition
Acceptable carrier in industry.Plant growth regulator composition of the present invention can also give birth in the plant of the present invention as needed
In long regulating composition, one or more of other insecticides, fungicide, a large amount of or trace-element fertilizer etc. are added, thus
Additional excellent results can be generated.
The dosage form of the composition of the present invention can be suspending agent, emulsion, microemulsion, wettable powder, water-dispersible granules
Deng in order to improve the utilization rate of active principle, suitable surfactant is usually added into formulated.
The advantages and positive effects of the present invention：
Adenine is introduced into α-naphthylacetic acid ester structure by compound of formula I of the present invention, and it is new to obtain a kind of structure
The plant growth regulator of grain husk.Wheat seed is impregnated with the 20 μ g/mL solution of plant growth regulator of the present invention for 24 hours, it can be notable
Improve wheat germination rate, germination promotion rate is much higher than the commodity such as DA-6,6-BA up to 36.9% (see example 2, table 1)；Promoting
Aspect of taking root is substantially better than DA-6, naphthalene methyl acetate, 6-BA (see example 3, table 2).Field experiment shows the plant growth regulating
Agent can make wheat increase yield 20-25%, make that corn stem is sturdy, leaf color is dark green and generous, extend leaf longevity, improve drought resisting, anti-
Flood, disease resistance increase production 24-28%；Accelerate apple with ripe color, improve soluble sugar and VC contents in apple, make mouthfeel more sweet,
Apple is expanded, improves level-one fruit rate, and prevents shedding, increases production nearly 25% (see example 4, table 2)；It is showed for tomato
Go out leaf color is dark green, fruit shape just, fruit is heavy, fruit-setting rate improves, the fresh preservation phase is long, increase production up to more than 25%.Compound of formula I is also
With bactericidal activity, to rhizoctonia cerealis (Rhizotonia cerealis), tomato early blight bacterium (Alternaria
Solanim), Rhizoctonia solani Kuhn (Rhizoctonia solani), phytophthora infestans (Phytophthora
Infestans) there is preventive and therapeutic effect.Compound of formula I not only has excellent plant growth regulating activity, but also the compound is simultaneous
With good fungicidal action, synthesis effect is substantially better than the plant growth regulator of single growth regulating-activity.Meanwhile
Purine and ester type compound easily biological-degradable, belong to environmentally friendly product.Plant growth regulator of the present invention have it is at low cost,
The advantages of safe and convenient to use, increasing yield and improving quality, disease prevention, has 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.
Synthesize example：
The preparation of example 1, compound of formula I
(1) preparation of naphthalene chloroacetic chloride
18.6g (0.1mol) methyl α-naphthyl acetates and 100mL toluene are separately added into 250mL three-necked flasks, 17.9g is added dropwise
The solution of (0.15mol) thionyl chloride and 30mL toluene composition, drop finish, are heated to flowing back, and are stirred to react 2h, and revolving removes solvent
Dichloromethane and thionyl chloride obtain pale yellowish oil liquid 19.4g, yield 94.6%.
(2) preparation of Formula II compound
15.5g (0.1mol) 6-chloropurines and 6.1g (0.1mol) ethanolamine are separately added into 250mL three-necked flasks,
100mL ethanol as solvent, is heated to reflux, and is stirred to react 3.5h, after the reaction was complete, cools down, filters, obtain pistac solid, dries
It is dry, obtain 15.6g, yield 87.1%.
(3) preparation of compound of formula I
It is separately added into 17.9g (0.1mol) Formula II compounds and 100mL toluene in 250mL three-necked flasks, 11.1g (0,
11mL) triethylamine makees acid binding agent, and the solution of 20.5g (0.1mol) naphthalene chloroacetic chlorides and 30mL toluene composition is added dropwise, and drop finishes, heats back
It flows down and is stirred to react 3.5h, TCL detections filter to obtain light yellow solid (compound of formula I) 28.8g, yield after the reaction was complete
83.0%, 186.6 DEG C~190.2 DEG C of fusing point.
Compound of formula I1H NMR (500MHz, DMSO-d6), δ (ppm)：3.750 (s, 2H, CH2), 4.107 (s, 2H,
CH2), 4.250-4.271 (t, 2H, CH2), 7.385-7.407 (m, 4H, CH), 7.901-7.907 (m, 4H, Ar-H), 8.127
(s, 2H, Ar-H), 12.951 (s, 1H, NH).
Example of formulations
The preparation of example 2,10% compound of formula I suspending agent：
15g compound of formula I, 2g sodium lignin sulfonates, 5 (Malaysias of 3g polycarboxylate salt dispersant Sokalan CP are weighed respectively
Acid-acrylic acid sodium salt), 1g organosilicon breasts antifoaming agent (the aqueous silicon emulsified antifoam agents of THIX-108), 2g aluminium-magnesium silicates and 5g second two
Alcohol adds in 77g water, stirs evenly in 250mL beakers, grinds 2h with sand mill, rotating speed is 3000 revs/min, detection granularity 3-5
μm, obtain white mobility suspending agent.
Biological activity determination
Example 2, Seeds Germination Tests
It is carried out using paper bed sproutung method.30% compound of formula I suspending agent, DA-6,6-BA are diluted to 5% Formulas I respectively
Compound suspending agent, 5%DA-6 aquas, 5%6-BA suspending agents are diluted with distilled water into concentration as 10 μ g/mL, 20 μ g/ respectively
ML, 30 μ g/mL, the plant growth regulator solution of 60 μ g/mL and 120 μ g/mL.Select the wheat that Seed size is uniform, full
Seed after being sterilized with hypochlorite solution to seed, is soaked seed with above-mentioned dilution in beaker and cultivates 8h, often handle 100
Seed, is uniformly placed in the culture dish of double-layer filter paper by seed, 3 repetitions after processing, kept between seed it is certain away from
From being well placed after seed and put it into 25 DEG C of heat preservation vernalization processing in complete intelligent climate box, during which periodically to add in distilled water
Filter paper is made to keep moistening, the germination of each processing is observed during vernalization, radicel length is standard about with the 1/2 of seed length, in
It counts wheat seed germination percentage in each culture dish afterwards for 24 hours, while is compared with DA-6,6-BA of same concentrations and clear water (CK),
Each dilution germination promotion rate is calculated simultaneously, it is as a result as shown in table 1 below.
1 wheat seed germinating of table is tested
By 1 experimental data of table as it can be seen that the wheat germination rate of formula Compound I processing is better than contrast agents on the whole
DA-6 and 6-BA is more significantly better than the situation of clear water processing (CK).
Example 3, the root experiment of seed soaking growth-promoting
30% suspending agent of compound of formula I, DA-6,6-BA are diluted to 5% compound of formula I suspending agent, 5%DA-6 respectively
Aqua, 5%6-BA suspending agents, be diluted with distilled water into respectively concentration for 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and
The plant growth regulator solution of 120 μ g/mL.The wheat seed that Seed size is uniform, full is selected, with hypochlorite solution to kind
It after son is sterilized, is soaked seed in beaker with above-mentioned dilution and cultivates 8h, often handle 20 wheats, 3 repetitions will kind after processing
Son is uniformly placed on the paper bed of moistening, is maintained a certain distance between seed, to ensure that seed fully absorbs moisture, when putting bed
Embryo portion is well placed after seed to put it into complete intelligent climate box and carries out vernalization processing for 24 hours upward towards the same side, during which
Periodically to add in distilled water makes paper bed keep moistening.It treats that wheat main root exposes 2mm or so, its kind is trained in the solid solidified
It supports in base, is then placed in complete intelligent climate box and is cultivated.It is high with calliper main root, stem after 40h, and make detailed note
Record.It is compared simultaneously with DA-6,6-BA of same concentrations and clear water processing (CK), it is as a result as shown in table 2 below.
2 wheat seed growth-promoting root of table is tested
The compounds of this invention reaches wheat seed soaking rush rooting efficiency in 30 μ g/mL concentration it can be seen from the result of table 2
To optimal, hence it is evident that better than control DA-6 and 6-BA.
Example 4, field experiment：3 processing are set altogether to apple experiment, each processing selects new upper 3 lifes of Gala apple tree
The comparable bough of growing way carries out, and experiment takes strain, tree-plot, 3 repetitions, respectively in red fuji apple young fruit period and fruit at random
Expanding stage respectively sprays once, and foliage-spray clear water after harvest, measures the index of quality of apple respectively as compareing, wherein, VC contains
Amount is measured using 2,6- dichloropheno-lindophenols method, and soluble sugar content is measured using anthrone colorimetry, as a result such as the following table 3.
3 apple quality index Test data of table
To sum up data, it can be seen that right while improving apple production after compound of formula I carries out foliage-spray to apple
The appearance and interior quality of apple are also significantly improved, it can be seen that the compound of the present invention is a kind of plant of excellent combination property
Object growth regulator.
Bactericidal activity measures
Example 5, by a certain amount of medicament dissolution in the appropriate n,N-Dimethylformamide (DMF), then with containing a certain amount of
Polysorbas20 emulsifier aqueous solution is diluted to 50mg/L.Using in vitro Plating, for trying pathogen：Botryosphaeria berengeriana f. sp
(Physalospora piricola), rhizoctonia cerealis (Rhizotonia cerealis), tomato early blight bacterium
(Alternaria solani), phytophthora infestans (Phytophthora infestans), Rhizoctonia solani Kuhn
(Rhizoctonia solani).Using biomass growth rate measuring method, detailed process is：Aseptically respectively draw 1mL
In liquid injection culture dish, 9mLPDA culture mediums (potato dextrose agar) are added in, 100mg/L is made after shaking up and contains
Medicine tablet does blank control with the tablet for adding 1mL aqua sterilisas.Bacterium disk is cut along mycelia outer rim with the card punch of diameter 4mm, is moved
To drug containing tablet, it is per treatment in triplicate.Culture dish is placed on culture in 24 ± 1 DEG C of constant incubators, is investigated after 72h each
Place's bacterium disk extension diameter, averages, and opposite bacteriostasis rate is calculated compared with blank control, and test concentrations are 100 μ g/mL, are tested
The result is shown in such as the following table 4.
Preventive effect (%)=(blank colony diameter-processing colony diameter)/(blank colony diameter -4) × 100%
Table 4 sterilization test preventive effect (%) data
By upper table data as it can be seen that compound of formula I is to Botryosphaeria berengeriana f. sp (Physalospora piricola), wheat line
Blight bacterium (Rhizotonia cerealis), tomato early blight bacterium (Alternaria solani), phytophthora infestans
(Phytophthora infestans), Rhizoctonia solani Kuhn (Rhizoctonia solani) have certain inhibitory action.
Claims (2)
1. a plant growth regulators, the adenine ethylnaphthalene acetate compounds of structure shown in formula I,
。
2. a kind of plant growth regulator composition contains compound of formula I described in claim 1 as active component and agricultural
Acceptable carrier in upper or forestry.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004064845A1 (en) * | 2003-01-14 | 2004-08-05 | Gilead Sciences, Inc. | Compositions and methods for combination antiviral therapy |
| WO2004110343A2 (en) * | 2003-06-13 | 2004-12-23 | Kyungdong Pharm. Co., Ltd. | 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]- 2- aminopurine using the same |
| WO2007092372A1 (en) * | 2006-02-03 | 2007-08-16 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| US8846694B2 (en) * | 2008-06-10 | 2014-09-30 | Merck Patent Gmbh | Pyrrolidone derivatives for use as MetAP-2 inhibitors |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004064845A1 (en) * | 2003-01-14 | 2004-08-05 | Gilead Sciences, Inc. | Compositions and methods for combination antiviral therapy |
| WO2004110343A2 (en) * | 2003-06-13 | 2004-12-23 | Kyungdong Pharm. Co., Ltd. | 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]- 2- aminopurine using the same |
| WO2007092372A1 (en) * | 2006-02-03 | 2007-08-16 | Cv Therapeutics, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| US8846694B2 (en) * | 2008-06-10 | 2014-09-30 | Merck Patent Gmbh | Pyrrolidone derivatives for use as MetAP-2 inhibitors |
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Effective date of registration: 20221019 Address after: 451450 yaojiaxiang, Zhongmou County, Zhengzhou City, Henan Province (east side of 223 provincial road) Patentee after: ZHENGZHOU NONGDA BIOCHEMICAL PRODUCT Co.,Ltd. Address before: 266000 Qingdao University of Science & Technology, 53 Zhengzhou Road, Shibei District, Qingdao, Shandong Patentee before: QINGDAO University OF SCIENCE AND TECHNOLOGY |