CN104926809B - A kind of pyrido pyrazoles urea sulfonate and application thereof - Google Patents
A kind of pyrido pyrazoles urea sulfonate and application thereof Download PDFInfo
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- CN104926809B CN104926809B CN201510181958.XA CN201510181958A CN104926809B CN 104926809 B CN104926809 B CN 104926809B CN 201510181958 A CN201510181958 A CN 201510181958A CN 104926809 B CN104926809 B CN 104926809B
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- urea
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- pyrazoles
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000004202 carbamide Substances 0.000 title claims abstract description 35
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical class C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 title claims abstract description 30
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 10
- 230000032823 cell division Effects 0.000 claims abstract description 9
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 230000001737 promoting effect Effects 0.000 claims description 2
- 239000003630 growth substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- 240000008067 Cucumis sativus Species 0.000 abstract description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 6
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 2
- 244000105624 Arachis hypogaea Species 0.000 abstract description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 2
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 2
- 230000003416 augmentation Effects 0.000 abstract description 2
- 235000020232 peanut Nutrition 0.000 abstract description 2
- 230000008635 plant growth Effects 0.000 abstract 1
- 231100000572 poisoning Toxicity 0.000 abstract 1
- 230000000607 poisoning effect Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- -1 Pyrido pyrazoles carbamide compound Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 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 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000009754 Vitis X bourquina Nutrition 0.000 description 6
- 235000012333 Vitis X labruscana Nutrition 0.000 description 6
- 240000006365 Vitis vinifera Species 0.000 description 6
- 235000014787 Vitis vinifera Nutrition 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000394 mitotic effect Effects 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- NNCUJGRWDISBCZ-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine-3-carboxamide Chemical class C1=CN=C2C(C(=O)N)=NNC2=C1 NNCUJGRWDISBCZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 240000001008 Dimocarpus longan Species 0.000 description 1
- 235000000235 Euphoria longan Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 1
- 229910003202 NH4 Inorganic materials 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- VRMWOQSSFPYAQD-UHFFFAOYSA-N [K].NC(N)=O Chemical compound [K].NC(N)=O VRMWOQSSFPYAQD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007812 deficiency Effects 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Landscapes
- 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)
Abstract
The invention discloses a kind of structure pyrido pyrazoles urea sulfonate shown in formula I and the purposes as plant growth regulator thereof.In formula: R1=H, R2=H, R3=H or CH3；R1=Cl, R2=Cl, R3=H or CH3；R1=H, R2=CH (CH3)2Or OCH3,R3=CH3Or H；M is selected from K, Na or NH4.Cucumber cotyledons augmentation test and Development of Peanut test show, compound of formula I is obviously promoted cell division, can regulating plant growth effectively.Compound of formula I as the active height of the basic element of cell division, soluble in water, be difficult to poisoning to occur and remains low advantage.
Description
Technical field
The invention belongs to plant growth regulator field in agricultural chemicals, be specifically related to a kind of pyrido pyrazoles urea sulfonate and application thereof.
Background technology
Plant growth regulator as the big class of in agricultural chemicals, improves and degeneration-resistant, disease-resistant etc. in increasing crop yield, precocity, quality
Aspect has played important function.The basic element of cell division is the plant growth regulator type that a class is important, has promotion cell division, increasing
Produce upgrading and strengthen the effect of crop anti-adversity.The basic element of cell division such as 6-benzyl aminopurine of commercialization, pyrido pyrazoles urea at present
(CPPU), N-(4-pyridine radicals)-N '-phenylurea (4-PU) and Thidiazuron etc..Xu Liangzhong et al. has invented a kind of Pyrazolopyridine
Carbamide compounds is used as plant growth regulator, has the characteristic feature of the basic element of cell division, and its activity is significantly better than the right of same concentration
Than medicament " Thidiazuron " (Xu Liangzhong, Wang Minghui etc., the patent No.: ZL 2013107334583；Publication No.: CN 103709158B,
A kind of Pyrazolopyridine carbamide compounds and application thereof).Further application test finds, though these compound activity are higher,
But it is water-insoluble, during use, needs to make missible oil, suspending agent etc., environment friendly and poor stability, plant absorption efficiency
Low.Recently the acardite sulfonate (formula II compound) of report is although having water solubility and safety in utilization, but its cell division
Activity is not ideal enough.In the prior art, pyrido pyrazoles urea sulfonate (type I compound) as representative of the present invention and thin
Born of the same parents' mitotic activity has no report.
Summary of the invention
It is an object of the invention to provide and a kind of prepare simplicity, use the safe efficient and pyrido pyrazoles urea sulfonic acid of good aqueous solubility
Salt plant growth regulator, it is mainly used as the basic element of cell division and promotes crop yield.
Pyrido pyrazoles carbamide compound disclosed in patent (publication No.: CN 103709158B) has the thinnest when low concentration
Born of the same parents' mitotic activity, can be used as expanding and improving yield and the quality of gourd, fruit and vegetable of the fruit such as apple, grape.But this compounds
Extremely difficult it is dissolved in water, it is difficult to develop the aqua preparation of greenization, be not easy to combine stable aqua product with other foliage fertilizers.This
Invent by phenyl ring in pyrido pyrazoles urea structure introduce sulfonic group, be prepared as water miscible pyrido pyrazoles urea potassium sulfonate,
Sodium or ammonium salt, not only overcome the deficiency that pyrido pyrazoles carbamide compound exists, also improve its work safety and plant absorption
Efficiency, has good compatibility with acid, alkaline and neutral foliage fertilizer, had both widened its range of application, is also beneficial to product and combines
Close the lifting of function.
Technical scheme is as follows:
The invention provides a kind of pyrido pyrazoles urea sulfonate, structure is as shown in formula I:
In formula: R1=H, R2=H, R3=H or CH3；R1=Cl, R2=Cl, R3=H or CH3；R1=H, R2=CH (CH3)2Or OCH3,
R3=CH3Or H；M is selected from K, Na or NH4。
Type I compound can be prepared by following reaction:
R in formula1, R, R3, M is as defined above.
Pyrido pyrazoles urea (formula III compound) reacts generation pyrido pyrazoles urea sulfonic acid in dichloroethanes with chlorosulfonic acid, in room
Temperature lower with 20～40% NaOH, 20～40% potassium hydroxide or ammoniacal liquor be neutralized to pH value 7, steam solvent, refluxing toluene dehydration
Obtain faint yellow solid, obtain type I compound of the present invention with isopropanol for solvent recrystallization.
Advantages of the present invention and good effect:
Compared with pyrido pyrazoles urea (formula III compound), type I compound of the present invention is soluble in water, can be configured to as required
The various concentration pyrido pyrazoles urea sulfonate aqueous solution, improve its work safety and plant absorption efficiency, to grape, apple
Spraying test result shows, the drug effect of type I compound is higher than pyrido pyrazoles urea (data are shown in Table 1～2), and type I compound
With other various foliage fertilizers, rush the compatibility such as fertilising and form the functional product having good stability, this is that pyrido pyrazoles urea is difficult to reality
Existing.Compared with formula II compound (acardite sulfonate), formula I Compound cellular mitotic activity is significantly better than known
Formula II compound (data are shown in Table 1～2).Field test shows, sprays under type I compound 1ppm concentration of the present invention, can
Grape particle is made to increase, simple grain average weight gain 40～42%, increase production 42～45%, the maturity period postpones 5 days；Apple can be made to increase production
45～50%, one-level fruit rate improves 48%；The vegetables such as cucumber, green pepper, tomato can be improved fruit-setting rate, increase production nearly 50%；Can make
Peanut yield increasing 30%.
In sum, type I compound of the present invention not only has volume increase and the comprehensive function of upgrading, and has ultra high efficiency, uses into
The good effects such as this low, safe ready, are a kind of efficient plant growth regulators with commercialization and market potential.
Formula I, when using as plant growth regulator, can be used alone, it is possible to other active components or leaf
Leaven is applied in combination, to provide the comprehensive function of product.
When preparing aqua preparation, generally add proper amount of surfactant and agricultural or forestry acceptable carrier.
It should be appreciated that, in scope defined by the claims of the present invention, various conversion and change can be carried out.
Detailed description of the invention
Following synthetic example and raw result of the test of surveying can be used to further illustrate the present invention, but are not intended to limit the present invention.
Synthesis example:
Example 1, the preparation of type I compound
With reference to the patent (patent No.: ZL 2013107334583；Publication No.: CN 103709158B) method prepares pyrido pyrrole
Azoles carbamide compound (formula III).The productivity of formula III compound is 85～95%.
(1) preparation of pyrido pyrazoles urea sulfonate sodium
Being sequentially added into 0.1mol formula III compound, 100mL 1,2-dichloroethanes in 250mL four-hole boiling flask, ice bath stirs
Lower addition 14g (0.12mol) chlorosulfonic acid, finishes, reacts at normal temperatures, is determined by thin-layer chromatography (TLC) after about 6h
Reaction end, after question response completes, cooling, the outstanding chlorosulfonic acid that solvent and excess are evaporated off, obtain pyrido pyrazoles urea sulfonic acid and (change
Compound IV).0.1mol formula IV compound, 100mL toluene, the 40%NaOH now joined it is sequentially added in 250mL four-hole bottle
Aqueous solution 10g (0.1mol), be to slowly warm up to reflux under stirring about 4h, detects extent of reaction with TLC, after having reacted,
Hang and solvent and water are evaporated off, obtain pyrido pyrazoles urea sulfonate sodium crude product, obtain faint yellow solid with recrystallisation from isopropanol.
Replace NaOH with potassium hydroxide or concentrated ammonia liquor, according to above method, can prepare pyrido pyrazoles urea sulfonic acid sylvite or
Ammonium salt.
The productivity of formula IV compound is 82～90%, and the productivity of type I compound is 88～95%.The equal ＞ of fusing point of type I compound
300℃。
Prepared by example 2, pyrido pyrazoles urea sulfonate aqua
Prepared by (1) 2% pyrido pyrazoles urea sulfonic acid potassium salt aqua
Weighing 2.0g pyrido pyrazoles urea sulfonic acid potassium salt, add 93g running water, stirring and dissolving, to clear solution, is subsequently adding 5g
Tween-80, stirs and i.e. obtains 2% pyrido pyrazoles urea sulfonic acid potassium salt aqua.
Prepared by (2) 5% pyrido pyrazoles urea sulfonate sodium aquas
Weigh 5.0g pyrido pyrazoles urea sulfonate sodium, add 90g running water, stirring and dissolving, be subsequently adding 5gNP-10 (nonyl
Phenol polyethenoxy ether), stirring and dissolving to clear i.e. obtains 5% pyrido pyrazoles urea sulfonate sodium aqua.
Prepared by (3) 10% pyrido pyrazoles urea sulfonic acid ammonium salt aquas
Weighing 10g pyrido pyrazoles urea sulfonic acid ammonium salt, add 80g running water, stirring and dissolving, to clear solution, is subsequently adding 10g
APG, stirs and i.e. obtains 10% pyrido pyrazoles urea sulfonic acid ammonium salt aqua.
Biological activity determination
Example 3, cucumber cotyledons augmentation test
It is that Tianjin grinds No. 4 for examination cucumber variety, sows after seed soaking in the enamel tray with cover filling 0.7% agar, be placed in 26 DEG C of Crape rings
Cultivating 72h under border, the cotyledon of selected size uniformity is stand-by, and sample preparation uses the filter in phytohormone activity substance-measuring
Paper disk method.
Specific practice is: according to example 2 method (2), type I compound sodium salt and formula II compound sodium salt are prepared as 2% aqua,
It is diluted with distilled water into 100 μ g mL again-1、10μg·mL-1The aqueous solution.By pyrido pyrazoles urea, Thidiazuron DMF (N, N-
Dimethylformamide) dissolve, add water and 5% Tween-80 is prepared as 0.5% missible oil, then be diluted with distilled water into 100 μ g mL-1、
10μg·mL-1Solution.Take each mother liquor 0.3mL respectively and uniformly drip on the filter paper of Φ 6cm, after solvent air-dries, at Φ 6cm
Culture dish in, respectively put into the filter paper 1 containing sample, add distilled water 3mL, cotyledon 10, be 10 and 1 μ g mL-1
Process.With distilled water for comparison, it is placed in 26 DEG C, cultivates under 3000Lux light intensity environment, after 72h, measure every 10 slice, thin piece leaf fresh weights.
Often processing 2 times and repeat, results averaged, result of the test is shown in Table 1.
From table 1 test data, type I compound of the present invention is significantly better than contrast II compound to cucumber cotyledons expansion activity,
At 10 μ g mL-1Time be significantly better than contrast commercialization Thidiazuron, at 1 μ g mL-1Time slightly be better than contrast commercialization Thidiazuron；
Compared with corresponding pyrido pyrazoles urea, also improve about 2～3%.
Table 1 cucumber cotyledons expansion contrast test
Example 4, grape experiment
Growth selection gesture, the plant that fruitful branch fineness degree is suitable longan grape as test maternal plant, 7 days florescences, full-bloom stage,
Spend latter 15 days and respectively spray with the liquid of 1ppm concentration, with clear water for comparison, gather after maturation and process and compare fruit ear and from respectively
Process and in the middle part of fruit ear, take 30 fruits at random, measure Single seed weight, statistics Single seed weight and yield, measure solvable with hand-held saccharous detector
Property solid content, the results are shown in Table 3.
Table 2 grape experiment result
By table 3 data it can be seen that compound of formula I is while promoting grape fruit to expand, increasing yield, moreover it is possible to improve Portugal
Grape sugar content.
To sum up data, it can be seen that the compound of the present invention is the plant growth regulator of a kind of excellent combination property.
Claims (3)
1. a pyrido pyrazoles urea sulfonate, structure is as shown in formula I:
In formula: R1=H, R2=H, R3=H or CH3；R1=Cl, R2=Cl, R3=H or CH3；R1=H, R2=CH (CH3)2Or OCH3,
R3=CH3Or H；M is selected from K, Na or NH4。
The purposes of a kind of pyrido pyrazoles urea sulfonate the most according to claim 1, it is characterised in that compound of formula I can be as planting
Thing growth regulator is used for promoting plant cell division and crop yield.
3. a plant growth regulator composition, containing the compound of formula I described in claim 1 as active component and agriculture or woods
Acceptable carrier in industry.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510181958.XA CN104926809B (en) | 2015-04-16 | 2015-04-16 | A kind of pyrido pyrazoles urea sulfonate and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510181958.XA CN104926809B (en) | 2015-04-16 | 2015-04-16 | A kind of pyrido pyrazoles urea sulfonate and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104926809A CN104926809A (en) | 2015-09-23 |
| CN104926809B true CN104926809B (en) | 2016-09-07 |
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Effective date of registration: 20231017 Address after: 454000 industrial cluster of Mengzhou City, Jiaozuo City, Henan Province Patentee after: Mengzhou Taoshiai Crop Protection 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 |