CN103709158B - Pyrazolopyrimidine ureas compound and application thereof - Google Patents
Pyrazolopyrimidine ureas compound and application thereof Download PDFInfo
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- CN103709158B CN103709158B CN201310733458.3A CN201310733458A CN103709158B CN 103709158 B CN103709158 B CN 103709158B CN 201310733458 A CN201310733458 A CN 201310733458A CN 103709158 B CN103709158 B CN 103709158B
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- 235000013877 carbamide Nutrition 0.000 title abstract description 3
- -1 Pyrazolopyrimidine ureas compound Chemical class 0.000 title abstract 2
- 239000005648 plant growth regulator Substances 0.000 claims description 8
- 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 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 27
- 230000000694 effects Effects 0.000 abstract description 7
- 230000008635 plant growth Effects 0.000 abstract description 4
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 230000033228 biological regulation Effects 0.000 abstract 1
- 239000003226 mitogen Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 230000032823 cell division Effects 0.000 description 7
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MOGQNVSKBCVIPW-UHFFFAOYSA-N 1-methylpyrazol-3-amine Chemical compound CN1C=CC(N)=N1 MOGQNVSKBCVIPW-UHFFFAOYSA-N 0.000 description 4
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000003416 augmentation Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 2
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 2
- LGWYXNMGKLYGAX-UHFFFAOYSA-N C1(=CC=CC=C1)N=C=O.[Cl] Chemical compound C1(=CC=CC=C1)N=C=O.[Cl] LGWYXNMGKLYGAX-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000005979 Forchlorfenuron Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- GPXLRLUVLMHHIK-UHFFFAOYSA-N forchlorfenuron Chemical compound C1=NC(Cl)=CC(NC(=O)NC=2C=CC=CC=2)=C1 GPXLRLUVLMHHIK-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- OFGUYIOIURBMCI-UHFFFAOYSA-N CC1[IH]c(nccc2)c2C(N)=N1 Chemical compound CC1[IH]c(nccc2)c2C(N)=N1 OFGUYIOIURBMCI-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YDPLFBIGFQFIDB-UHFFFAOYSA-N N#Cc1ncccc1Cl Chemical compound N#Cc1ncccc1Cl YDPLFBIGFQFIDB-UHFFFAOYSA-N 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
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 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 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 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<
- A01N47/36—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
Abstract
The invention discloses a pyrazolopyrimidine ureas compound with a novel structure, wherein the structure is shown as formula I, and the definition of each group in the formula is shown in the specification. The compound represented by the formula I has excellent plant growth regulation activity, and particularly can be taken as plant cell mitogen for agriculturally regulating the plant growth and improving the yield.
Description
Technical field
The invention belongs to plant growth regulator field in agricultural chemicals, be specifically related to a kind of Pyrazolopyridine carbamide compounds and application thereof.
Background technology
Plant growth regulator, as the large class of one in agricultural chemicals, has played important function in increasing crop yield, precocity, quality improve and be degeneration-resistant, disease-resistant etc.
Plant growth regulator is divided into the large class of growth hormone, gibberellin, ethrel, the basic element of cell division and abscisic acid five, wherein the basic element of cell division in promotion plant cell division, delay plant leaf surface aging, increase in stem tuber and fruit yield etc. there is important function.
At present agriculturally conventional cell division have 6-benzyl aminopurine, forchlorfenuron and Thidiazuron, and wherein forchlorfenuron and Thidiazuron are the ureas basic element of cell division, wherein Thidiazuron be also used as cotton gather before cotton defoliant.
The weak point of above-mentioned cytokinin compound is that synthesis step is long, production cost is high, production process three-waste pollution is serious, and therefore Development and Production technique is simple, cost is low, the basic element of cell division kind of high-efficiency environment friendly is significant.
The people such as Mosaad Sayed Mohamed report compound (formula II) and active anticancer (Design thereof, Synthesis andCancer Cell Line Activities of Pyrazolo [3, 4-b] pyridine Derivatives, Mosaad SayedMohamed, Moustafa El-Araby, Open Journal of Medicinal Chemistry, 2012, 2, 78-88), although formula II compound structurally has similarity with the compounds of this invention, but in the prior art, physical property and the plant growth regulating activity thereof of Pyrazolopyridine carbamide compounds as described in the present invention have no report.
Summary of the invention
The object of the present invention is to provide a kind of Pyrazolopyridine carbamide compounds of novel structure, it can be used for agriculture increasing crop yield or growth regulation.
Technical scheme of the present invention is as follows:
The invention provides a kind of Pyrazolopyridine carbamide compounds, as shown in general formula I:
In formula: R
1be selected from H or CH
3;
R
2be selected from H or Cl;
R
3be selected from H or Cl.
Formula I can be obtained by following reaction:
In formula, each group definition is the same.
Formula III compound and formula IV compound room temperature reaction 2h in suitable solvent obtains the compounds of this invention (formula I).
Suitable solvent is selected from carrene, dichloroethane, ethyl acetate, acetonitrile, dioxane, DMF (DMF), dimethyl sulfoxide (DMSO) etc., and the preparation method of formula III compound is shown in that the present invention synthesizes example.
Table 1 lists structure and the physical property of segment bounds I.
The structure of table 1 segment bounds I and physical property
| Compound | R 1 | R 2 | R 3 | Outward appearance | Fusing point/DEG C |
| I a | H | H | H | Buff powder | 288-291 |
| I b | H | H | Cl | Buff powder | >300 |
| I c | H | Cl | Cl | Buff powder | >300 |
| I d | CH 3 | H | H | Buff powder | 245-248 |
| I e | CH 3 | H | Cl | Buff powder | 267-269 |
| I f | CH 3 | Cl | Cl | Buff powder | 251-254 |
The advantage of the compounds of this invention (formula I) and good effect:
The present invention makes public for the first time the plant growth regulating activity of Pyrazolopyridine carbamide compounds, compared with existing commercial phytocytomine (as Thidiazuron), have production technology simple, raw material is easy to get, production process safety and environmental protection and active high, low cost and other advantages; Cucumber cotyledons augmentation test shows, the compounds of this invention has the characteristic feature of the basic element of cell division, its activity is significantly better than the contrast agents " Thidiazuron " of same concentration, show cucumber cotyledons and significantly thicken increase, blade weightening finish is extremely remarkable, even if under 1ppm and 0.1ppm concentration, Cotyledon expansion test also reaches beyond thought significance level, and therefore the compounds of this invention also comprises the purposes as plant growth regulator.
The compounds of this invention, when using as plant growth regulator, can be used alone, and also can use with other active substance combination, to provide the combination property of product.
The present invention also comprises the plant growth regulator composition of formula I as active component, and said composition comprises formula I as active component and agriculturally acceptable carrier.
Composition of the present invention can use using the form of preparation: formula I is dissolved in or is scattered in as active component in carrier or solvent, adds appropriate surfactant and makes missible oil, suspending agent, microemulsion etc.
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 result of the test of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthesis example:
Example 1, Compound I
a, I
b, I
cpreparation
(1) 3-amino-pyrazol the synthesis of pyridine
13.8g(0.1mol is added respectively in 250mL there-necked flask) the chloro-nicotinonitrile of 2-and 100mL absolute ethyl alcohol, stir lower dropping 80% hydrazine hydrate 10.6g(0.2mol), stirring at room temperature reaction 2h, separate out a large amount of red-brown precipitations, suction filtration, use ethanol in proper amount washing leaching cake, dry, obtain light brown powder 13.0g, yield 98.0%, fusing point: 184-185 DEG C.
(2) I
athe synthesis of compound:
6.7g (0.05mol) 3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir the mixed liquor that lower room temperature drips 6.0g phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dries, obtain 12.2g buff powder, yield 97.0%.
(3) I
bthe preparation of compound
6.7g (0.05mol) 3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir lower room temperature and drip the mixed liquor of 7.8g to chlorine phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dries, obtain 13.6g buff powder, yield 94.6%.
(4) I
cthe preparation of compound
6.7g (0.05mol) 3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir lower room temperature and drip 9.6g3, the mixed liquor of 4-dichloro phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dry, obtain 14.6g buff powder, yield 90.6%.
Example 2, Compound I
d, I
e, I
fthe preparation of compound
(1) 1-N-methyl-3-amino-pyrazol the synthesis of pyridine
13.8g(0.1mol is added respectively in 250mL there-necked flask) the chloro-nicotinonitrile of 2-and 100mL absolute ethyl alcohol, methyl hydrazine 9.2g(0.2mol is added) under stirring, stirring at room temperature reaction 2h, separate out a large amount of red-brown precipitations, suction filtration, use ethanol in proper amount washing leaching cake, dry, obtain light brown powder 13.9g, yield 93.9%, fusing point: 104-106 DEG C.
(2) I
dthe preparation of compound
7.4g (0.05mol) 1-N-methyl-3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir the mixed liquor that lower room temperature drips 6.0g phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dries, obtain 12.5g buff powder, yield 93.6%.
(3) I
ethe preparation of compound
7.4g (0.05mol) 1-N-methyl-3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir lower room temperature and drip the mixed liquor of 7.8g to chlorine phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dries, obtain 14.2g buff powder, yield 94.2%.
(4) I
fthe preparation of compound
7.4g (0.05mol) 1-N-methyl-3-amino-pyrazol is added respectively and pyridine and 80mL ethyl acetate in 250mL there-necked flask, stir lower room temperature and drip 9.6g3, the mixed liquor of 4-dichloro phenyl isocyanate and 20mL ethyl acetate, drip and finish, continue at stirring at room temperature reaction 2h, suction filtration, filter cake 20mL ethyl acetate washs once, dry, obtain 15.9g buff powder, yield 94.6%.
I
a-I
fthe hydrogen spectrum nuclear magnetic data of compound is as follows:
I
acompound:
1hNMR (500MHz, DMSO), δ/ppm:7.749-8.596 (m, 3H, Pyridyl-H), 7.234-7.665 (m, 5H, Ar-H), 6.224 (s, 2H, NH), 13.696 (s, 1H, NH);
I
bcompound:
1hNMR (500MHz, DMSO), δ/ppm:7.751-8.598 (m, 3H, Pyridyl-H), 7.253-7.586(m, 4H, Ar-H), 6.225 (s, 2H, NH), 13.701 (s, 1H, NH);
I
ccompound:
1hNMR (500MHz, DMSO), δ/ppm:7.450-8.603 (m, 3H, Pyridyl-H), 7.234-7.637 (m, 3H, Ar-H), 6.209 (s, 2H, NH), 13.685 (s, 1H, NH);
I
dcompound:
1hNMR (500MHz, DMSO), δ/ppm:7.469-8.567 (m, 3H, Pyridyl-H), 7.016-7.642 (m, 5H, Ar-H), 6.198 (s, 2H, NH), 3.798 (s, 3H, CH3);
I
ecompound:
1hNMR (500MHz, DMSO), δ/ppm:7.508-8.587 (m, 3H, Pyridyl-H), 7.236-7.594 (m, 4H, Ar-H), 6.217 (s, 2H, NH), 3.771 (s, 3H, CH3);
I
fcompound:
1hNMR (500MHz, DMSO), δ/ppm:7.746-8.576 (m, 3H, Pyridyl-H), 7.183-7.648 (m, 3H, Ar-H), 6.202 (s, 2H, NH), 3.798 (s, 3H, CH3).
Biological activity determination
Example 3, cucumber cotyledons augmentation test
Examination cucumber variety is supplied to be that Tianjin grinds No. 4, after seed soaking, sowing is in the enamel tray with cover filling 0.7% agar, 72h is cultivated under being placed in 26 DEG C of dark situations, the cotyledon of selected size uniformity is stand-by, sample preparation adopts the filter paper enzyme in phytohormone activity substance-measuring, and sample test concentration is 10,1 and 0.1 μ gmL
-1, solvent is DMF(N, dinethylformamide).
Specific practice is: be 100,10,1 μ gmL by sample preparation
-1dMF(N, dinethylformamide) mother liquor, then get each mother liquor 0.3mL respectively and evenly drip on the filter paper of Φ 6cm, after solvent is air-dry, in the culture dish of Φ 6cm, respectively put into the filter paper 1 containing sample, add distilled water 3mL, cotyledon 10, be 10,1 and 0.1 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, record result, result of the test is in table 2.
Table 2 Compound I cucumber cotyledons augmentation test
Table 2 Activity Results shows, part of compounds of the present invention has more excellent cytokine activity compared with control compounds Thidiazuron.
Claims (2)
1. structure is such as formula the purposes of the Pyrazolopyridine carbamide compounds shown in I as plant growth regulator,
In formula: R
1be selected from H or CH
3; R
2be selected from H or Cl; R
3be selected from H or Cl.
2. a plant growth regulator composition, containing the formula I described in claim 1 as active component and agriculturally acceptable carrier.
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| CN104926809B (en) * | 2015-04-16 | 2016-09-07 | 青岛科技大学 | A kind of pyrido pyrazoles urea sulfonate and application thereof |
| CN105037358A (en) * | 2015-09-06 | 2015-11-11 | 青岛科技大学 | Pyrazole and pyridine urea benzenesulfonic acid and salt compound and application thereof |
| CN107827885A (en) * | 2017-11-17 | 2018-03-23 | 昌邑市龙港无机硅有限公司 | A kind of 2,4 two cinnamoyl chloride thioureas of Pyrazolopyridine substitution and its application |
| CN116874541B (en) * | 2023-07-17 | 2024-02-20 | 潍坊市阳光化工股份有限公司 | Plant growth regulator and preparation method thereof |
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| CN103709158A (en) | 2014-04-09 |
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