CN104926718A - Forchlorfenuron sulfonate and use thereof - Google Patents
Forchlorfenuron sulfonate and use thereof Download PDFInfo
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- CN104926718A CN104926718A CN201510157287.3A CN201510157287A CN104926718A CN 104926718 A CN104926718 A CN 104926718A CN 201510157287 A CN201510157287 A CN 201510157287A CN 104926718 A CN104926718 A CN 104926718A
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- forchlorfenuron
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- compound
- sulfonate
- plant
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- 239000005979 Forchlorfenuron Substances 0.000 title claims abstract description 41
- GPXLRLUVLMHHIK-UHFFFAOYSA-N forchlorfenuron Chemical compound C1=NC(Cl)=CC(NC(=O)NC=2C=CC=CC=2)=C1 GPXLRLUVLMHHIK-UHFFFAOYSA-N 0.000 title claims abstract description 40
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 9
- 230000032823 cell division Effects 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 11
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 8
- 244000105624 Arachis hypogaea Species 0.000 abstract description 8
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 8
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 8
- 235000020232 peanut Nutrition 0.000 abstract description 8
- 240000008067 Cucumis sativus Species 0.000 abstract description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 6
- 238000002474 experimental method Methods 0.000 abstract description 6
- 238000011161 development Methods 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 206010000060 Abdominal distension Diseases 0.000 abstract 1
- 231100000674 Phytotoxicity Toxicity 0.000 abstract 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 abstract 1
- 239000004062 cytokinin Substances 0.000 abstract 1
- 230000008635 plant growth Effects 0.000 abstract 1
- 235000011430 Malus pumila Nutrition 0.000 description 15
- 235000015103 Malus silvestris Nutrition 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 235000013399 edible fruits Nutrition 0.000 description 11
- -1 forchlorfenuron sulfonic acid ammonium salt Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000007787 solid 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 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
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000220225 Malus Species 0.000 description 2
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WZYOSMAXXLCTGP-UHFFFAOYSA-N 1-phenyl-3-pyridin-4-ylurea Chemical compound C=1C=NC=CC=1NC(=O)NC1=CC=CC=C1 WZYOSMAXXLCTGP-UHFFFAOYSA-N 0.000 description 1
- 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
- RNMDNPCBIKJCQP-UHFFFAOYSA-N 5-nonyl-7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-ol Chemical compound C(CCCCCCCC)C1=C2C(=C(C=C1)O)O2 RNMDNPCBIKJCQP-UHFFFAOYSA-N 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 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
- 229920000742 Cotton Polymers 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
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts 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
- 230000003416 augmentation Effects 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 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
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 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
- 230000000394 mitotic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 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
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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 forchlorfenuron sulfonate with a structure shown as formula I and a use thereof as a plant growth regulator. In the formula as shown in the specification, M is selected from K, Na or NH4. Cucumber cotyledon distention experiments and peanut growing development experiments indicate that the compound of formula I obviously promotes cell division and can effectively regulate and control plant growth. The compound of formula I as a cytokinin has the advantages of being high in activity, soluble in water, unlikely to cause phytotoxicity, low in cost and low in residue.
Description
Technical field
The invention belongs to plant-growth regulator field in agricultural chemicals, be specifically related to a kind of forchlorfenuron sulfonate and uses thereof.
Background technology
Phytokinin is the important plant-growth regulator type of a class, has the effect promoting cell fission, increasing yield and improving quality and strengthen crop anti-adversity.Current commercial phytokinin is as 6-benzyl aminopurine, forchlorfenuron (CPPU), N-(4-pyridyl)-N '-phenylurea (4-PU) and thidiazuron etc.(chemical name: N-(2-chloro-4-pyridyl-N '-phenylurea) its physiologically active is higher than general purine type phytokinin (its biological activity comparatively 6-benzyl aminopurine height 10-100 times) for forchlorfenuron, there are promotion cell fission, cell expansion, acceleration fruit thinning and fallen leaves, delay effect (the high Kingsoft etc. such as plant senescence, the progress of phytokinin CPPU, agricultural chemicals, 2006,45 (3): 151-154).Though these compound activity are higher, be water-insoluble, safety in utilization is poor and be difficult to and other active ingredient compatibilities., although have water-soluble and safety in utilization, its cell division activity is not ideal enough for the sym-diphenylurea sulfonate (formula II compound) of recent report.In the prior art, forchlorfenuron sulfonate (type I compound) as representative of the present invention and cell division activity thereof have no report.
Summary of the invention
The object of this invention is to provide a kind of forchlorfenuron sulfonate plant-growth regulator preparing easy, use safety, efficient and good aqueous solubility, it is mainly used as phytokinin and promotes crop yield.
Forchlorfenuron has good cell division activity when lower concentration, is at present mainly used as apple, grape, Kiwifruit, the expanding and improve the seed output and quality of gourd, fruit and vegetable of pear and other fruits; It is used as the fallen leaves of the fruit thinning of the fruit such as apple, tomato, pineapple, flower thinning and cotton, soybean crops harvesting time when high density.But this compound pole is insoluble in water, is difficult to the aqua preparation developing greenization, also not easily combines stable aqua product with other foliage fertilizers.The present invention is by phenyl ring introducing sulfonic group in forchlorfenuron structure, be prepared into water miscible forchlorfenuron potassium sulfonate, sodium or ammonium salt, not only overcome the deficiency that forchlorfenuron exists, also improve its work safety and plant absorption efficiency, good compatibleness is had with acid, alkaline and neutral foliage fertilizer, both widen its range of application, be also conducive to the lifting of product comprehensive function.
Technical scheme of the present invention is as follows:
The invention provides a kind of forchlorfenuron sulfonate, structure is as shown in formula I:
In formula: M is selected from K, Na or NH
4.
Type I compound can be obtained by following reaction:
In formula, M definition is the same.
Forchlorfenuron generates forchlorfenuron sulfonic acid with chlorosulfuric acid in methylene dichloride (or ethylene dichloride), control temperature 10-20 DEG C, with 20% sodium hydroxide, 20% potassium hydroxide or ammonia neutralization to pH value 7, steam solvent, refluxing toluene dewaters to obtain white solid, obtains type I compound of the present invention through Virahol purifying.
Advantage of the present invention and positively effect:
Compared with commercial forchlorfenuron, type I compound of the present invention is soluble in water, the various concentration forchlorfenuron sulfonate aqueous solution can be mixed with as required, improve its work safety and plant absorption efficiency, grape, apple spraying test result are shown, the drug effect of type I compound higher than forchlorfenuron (data are in Table 1-4), and type I compound and other various foliage fertilizers, rushed the compatibility such as to apply fertilizer and is formed the functional product had good stability, and this is that forchlorfenuron is difficult to realize.Compared with formula II compound (sym-diphenylurea sulfonate), formula I Compound cellular mitotic activity is significantly better than known formula II compound (data are in Table 1-4).Field test shows, sprays under type I compound 1ppm concentration of the present invention, grape particle can be made to increase, simple grain average weight gain 39%, volume increase 42%, and the ripening stage postpones 5 days; Apple can be made to increase production 45%, and one-level fruit rate improves 40%, and improves soluble sugar content in apple, and the painted and mouthfeel of apple is obviously improved; Fruit-setting rate can be improved, volume increase 45-50% to vegetables such as cucumber, green pepper, tomatoes; Peanut yield increasing 25% can be made, soybean yield-increasing 22%.
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, produces the positively effects such as easy, use cost is low, safe ready, is a kind of efficient plant growth regulator with commercialization and market potential.
Formula I, when using as plant-growth regulator, can be used alone, and also can combinationally use with other active ingredients or foliage fertilizer, to provide the comprehensive function of product.
When preparing aqua preparation, usually add proper amount of surfactant and agriculture or forestry acceptable carrier.
Should it is clear that, in claim limited range of the present invention, can various conversion and change be carried out.
Embodiment
Following synthetic example and raw test-results of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthesis example:
The preparation of example 1, type I compound
(1) preparation of forchlorfenuron sulfonic acid potassium salt
24.77g (0.1mol) forchlorfenuron and 100mL methylene dichloride is added respectively in 250mL there-necked flask, the solution be made up of 12.82g (0.11mol) chlorsulfonic acid and 30mL methylene dichloride is dripped under stirring at room temperature, molten complete, at 20-40 DEG C of stirring reaction 3h, with 20%KOH solution temperature control less than 20 DEG C, reaction solution is neutralized to about pH=7.Revolve and steam removing methylene chloride, refluxing toluene dehydration is extremely anhydrous, suction filtration, dry, obtain white solid, by gained solid 150mL Virahol heating for dissolving, filtering insolubles (inorganic salt) while hot, filtrate naturally cools to room temperature, suction filtration, filter cake with appropriate isopropyl alcohol wash once, suction filtration, dry, obtain white solid powder 31.45g, productive rate 86%.Fusing point: 184.0-186.5 DEG C.
1H NMR(500MHz,DMSO)，δ/ppm：8.648-8.656(m,1H,Pyridyl-H)，6.940-6.971(m,2H,Pyridyl-H)，7.918-7.928(m，4H，H-Ar)，6.05(2H，-NH)。
(2) preparation of forchlorfenuron sulfonate sodium
Replace methylene dichloride with ethylene dichloride, adopt aforesaid method to prepare forchlorfenuron sulfonic acid, then with 20%NaOH solution, reaction solution is neutralized to about pH=7.Revolve and steam except desolventizing ethylene dichloride, refluxing toluene dehydration is to anhydrous, and suction filtration, with recrystallisation from isopropanol, obtains white solid powder forchlorfenuron sodium sulfonate.
Replace sodium hydroxide with strong aqua, according to above method, forchlorfenuron sulfonic acid ammonium salt can be obtained.
Prepared by example 2, forchlorfenuron sulfonate aqua
(1) 2% forchlorfenuron sulfonic acid potassium salt aqua preparation
Take 2.0g forchlorfenuron sulfonic acid potassium salt, add 93g tap water, stirring and dissolving, to clear solution, then adds 5g tween-80, stirs and obtains 2% forchlorfenuron sulfonic acid potassium salt aqua.
(2) 5% forchlorfenuron sulfonate sodium aqua preparations
Take 5.0g forchlorfenuron sulfonate sodium, add 90g tap water, stirring and dissolving, then add 5gNP-10 (polyoxyethylene nonylphenol ether), namely stirring and dissolving to clear obtains 5% forchlorfenuron sulfonate sodium aqua.
(3) 10% forchlorfenuron sulfonic acid ammonium salt aqua preparations
Take 10g forchlorfenuron sulfonic acid ammonium salt, add 80g tap water, stirring and dissolving, to clear solution, then adds 10g alkyl glycoside, stirs and obtains 10% forchlorfenuron sulfonic acid ammonium salt aqua.
Biological activity determination
Example 3, cucumber cotyledons augmentation test
Supply examination cucumber variety to be that Tianjin grinds No. 4, after seed soaking, sowing is in the enamel tray with cover filling 0.7% agar, and cultivate 72h under being placed in 26 DEG C of dark situations, the cotyledon of selected size uniformity is stand-by, the filter paper enzyme in sample preparation employing phytohormone activity substance-measuring.
Specific practice is: type I compound forchlorfenuron sulfonate and formula II potassium Compound Salt are prepared into 2% forchlorfenuron sulfonic acid potassium salt aqua according to example 2 method (1) and are prepared as 100 μ gmL with distilled water again
-1, 10 μ gmL
-1the aqueous solution.Forchlorfenuron ethanol in proper amount is dissolved, to add water and 5% tween-80 is prepared into 0.5% missible oil, then be diluted with distilled water into 100 μ gmL
-1, 10 μ gmL
-1solution.Getting each mother liquor 0.3mL respectively evenly drips on the filter paper of Φ 6cm, after solvent is air-dry, in the culture dish of Φ 6cm, respectively puts into the filter paper 1 containing sample, adds distilled water 3mL, cotyledon 10, be 10 and 1 μ gmL
-1process.Take distilled water as contrast, be placed in 26 DEG C, cultivate under 3000Lux light intensity environment, after 72h, measure every 10 slice, thin piece leaf fresh weights.Often process and repeat for 2 times, results averaged, test-results is in table 1.
Table 1 cucumber cotyledons expansion simultaneous test
From table 1 testing data, type I compound of the present invention is significantly better than contrast II compound to cucumber cotyledons expansion activity.
Example 4, Development of Peanut are tested
At the aqueous solution of peanut seedling spraying forchlorfenuron sulfonate, investigate the impact on Development of Peanut, spraying concentration is 1ppm, and the results are shown in Table 2.
Table 2 Development of Peanut is tested
| Compound | Plant height (cm) | Side shoot long (cm) | Branch amount (bar) | Individual plant flower amount (piece) | Individual plant young fruit number (individual) |
| Type I compound sylvite | 17.2 | 23.2 | 14 | 37 | 32 |
| Type I compound sodium salt | 17.0 | 23.0 | 13 | 36 | 32 |
| Type I compound ammonium salt | 17.3 | 23.2 | 14 | 36 | 31 |
| Forchlorfenuron | 16.0 | 21.5 | 12 | 33 | 29 |
| Formula II potassium Compound Salt | 14.2 | 18.2 | 9 | 26 | 22 |
| Clear water contrasts | 12.0 | 17.0 | 7 | 24 | 20 |
As can be seen from Table 2, after spraying the compounds of this invention, obviously facilitate the robust growth of peanut, absolutely prove that the compounds of this invention can regulate and control peanut nutrition growth and reproductive growth, for increasing yield and improving quality has laid solid foundation effectively as plant-growth regulator.
Example 5, grape experiment
The longan grape of growth selection gesture, plant that fruitful branch fineness degree is suitable is as test maternal plant, 7 days florescences, full-bloom stage, spend after within 15 days, respectively spray with the liquid of 1ppm concentration, take clear water as contrast, gather after maturation and process and contrast fruit ear and get 30 fruits at random in the middle part of each process fruit ear, measure Single seed weight, statistics Single seed weight and output, measure soluble solid content with hand-held saccharous detector, the results are shown in Table 3.
Table 3 grape experiment result
As can be seen from table 3 data, formula I is expanded at promotion grape fruit, while increase yield, can also be improved grape sugar content.
Example 6, apple are tested
Field experiment: 3 process are established altogether to apple experiment, the bough that the new Gala apple of each processing selecting sets upper 3 growth potentials suitable carries out, test gets strain at random, tree-plot, repeat for 3 times, respectively spray once (concentration is 1ppm) at red fuji apple young fruit period and fruit expanding period respectively, foliage-spray clear water in contrast, after results, measure the quality parameter of apple respectively, wherein, VC content adopts 2,6-Dichlorophenol indophenol method measures, and soluble sugar content adopts anthrone colorimetry to measure, and result is as following table 4.
Table 4 apple quality index Test data
As can be seen from table 4 data, after formula I carries out foliage-spray to apple, improve while apple production, be also significantly improved to the outward appearance of apple and interior quality, VC and soluble sugar content are obtained for raising.
To sum up data, can find out that compound of the present invention is a kind of plant-growth regulator of excellent combination property.
Claims (3)
1. a forchlorfenuron sulfonate, structure is as shown in general formula I:
In formula: M is selected from K, Na or NH
4.
2. the purposes of a kind of forchlorfenuron sulfonate according to claim 1, is characterized in that formula I can be used as plant-growth regulator for promoting plant cell division and crop yield.
3. a plant growth regulator composition, containing formula I according to claim 1 as acceptable carrier in active ingredient and agricultural or forestry.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105503711A (en) * | 2016-01-30 | 2016-04-20 | 山西大学 | Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof |
| CN106986732A (en) * | 2017-05-22 | 2017-07-28 | 金正大生态工程集团股份有限公司 | A kind of urea fertilizer of sustained-release synergistic and preparation method thereof |
| CN107129368A (en) * | 2017-05-22 | 2017-09-05 | 金正大生态工程集团股份有限公司 | A kind of fertilizer synergist and preparation method and application |
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| CN1223789A (en) * | 1998-01-23 | 1999-07-28 | 山西大学 | Plant growth regulator and its preparing process |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503711A (en) * | 2016-01-30 | 2016-04-20 | 山西大学 | Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof |
| CN105503711B (en) * | 2016-01-30 | 2017-10-17 | 山西大学 | A kind of pyridine urea bi-quaternary ammonium salt and its preparation method and application |
| CN106986732A (en) * | 2017-05-22 | 2017-07-28 | 金正大生态工程集团股份有限公司 | A kind of urea fertilizer of sustained-release synergistic and preparation method thereof |
| CN107129368A (en) * | 2017-05-22 | 2017-09-05 | 金正大生态工程集团股份有限公司 | A kind of fertilizer synergist and preparation method and application |
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