CN104311598A - Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof - Google Patents
Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a phosphate compound containing a 1,2,3-triazole ring as well as a preparation method and an application thereof. The structural formula of the phosphate compound containing the 1,2,3-triazole ring is shown as a formula (I). According to the method for preparing the phosphate compound containing the 1,2,3-triazole ring disclosed by the invention, the raw materials are low in price and readily available, the reaction route is simple, and the phosphate compound containing the 1,2,3-triazole ring is high in herbicidal activity. The measurement result of the herbicidal activity plating method proves that the phosphate compound has strong effects of inhibiting growth of roots and stems of wheat and oilseed rapes. The pot experiment proves that the phosphate compound has a good effect of inhibiting growth of barnyard grass. The phosphate compound containing the 1,2,3-triazole ring has high plant growth regulation activity and high herbicidal activity during low concentration.
Description
Technical field
The present invention relates to a kind of phosphate compound containing 1,2,3-triazoles ring and its preparation method and application.
Background technology
Chemical structure very important in the research fields such as agricultural chemicals, medicine and veterinary drug containing the heteroatomic heterocyclic ring compounds such as N, S, P, because of the difference of its fine structure, this compounds often has unique sterilization, desinsection, kills mite, weeding and plant growth regulating isoreactivity, is agriculturally having a wide range of applications.The commercialization of current many such agricultural chemicals, has good biological activity.Contriver is containing 1, 3, multiple serial active structure is obtained in the compou nd synthesis of 4-thiadiazole ring structure and bioactivity research, as 2-hexa-methylene-5-(substituted imine base)-1, 3, 4-thiazoline, 2-ten dimethylene-5-(substituted imine base)-1, 3, 4-thiazoline, macrolide/lactan-1, 3, 4-thiazoline, 1 of furyl glycosyl modification, 3, 4-thiazole and containing chlorocyclopropane 1, 3, 4-3-triazole compounds etc. has good fungicidal activity mostly, part has the value of exploitation further, some compounds are especially containing 1 of chlorocyclopropane, 3, 4-3-triazole compounds demonstrates good plant growth regulating activity.
In plant-growth regulator, the uniconazole containing 1,3,4-triazole ring structure and paclobutrazol are comparatively early commercial kinds.Contriver showed the research of 1,3,4-3-triazole compounds in early stage, novel chloro cycloalkyl is introduced to the modification of these structures, in reservation with while improving 1,3,4-triazole plant growth regulating activity, the existing commercial kind longevity of residure can be overcome to a certain extent long, the deficiency that selectivity is low, however, the plant-growth regulator molecule of design, synthesis novelty, find efficient, high reactivity new plant growth regulator is the emphasis that contriver pays close attention to always.In New pesticides discovery, be the important channel that environment friendly agricultural guide finds based on target molecules design.Imidazoleglycerol phosphate dehydratase is the potential target enzymes that the class in recent years found has plant growth regulating activity.This enzyme is positioned at the 7th step of histidine biosynthesis reaction, and generating imidazole acetolphosphate by imidazoleglycerol phosphate through dehydration reaction, is one of key enzyme of histidine biosynthesis in involved in plant body.By regulating the activity of this enzyme system, the generation of imidazole acetolphosphate can be regulated, and then affect the biosynthesizing of Histidine, reach the object of growth of suppression, regulating plant.
Therefore, under country ten two five " 863 " plans the subsidy of problem (No:2011AA10A206) and National Nature fund (No.21172257), according to the basis of contriver seminar early-stage Study, we are based on the chemical structure of imidazoleglycerol phosphate Dehydratases catalyse intermediate transition state " phenodiazine fulvalene ", design a class and contain 1, 2, 3-triazole, phosphoric acid ester, the novel compound of carboxylicesters, and plant growth regulating activity mensuration has been carried out to this compounds, find that a class lower concentration has high plant growth regulating activity and has the novel structure of weeding activity concurrently.
Summary of the invention
The object of this invention is to provide a kind of phosphate compound or its pharmacy acceptable salt that contain 1,2,3-triazoles ring.
Phosphate compound (CAU2014-JY) containing 1,2,3-triazoles ring or its pharmacy acceptable salt, the structural formula of the described phosphate compound containing 1,2,3-triazoles ring is for shown in formula (I).
In formula (I), R
1for the phenyl of ethoxycarbonyl, chloromethyl, the tertiary butyl, phenyl or replacement, the substituting group on the phenyl of described replacement is any one halogen, substituting group be 2 replacements, 3 replace or 4 replacements;
R
2for methyl, 2-chloropyridine base, menaphthyl or with 1 ~ 2 substituent phenyl, described is halogen or nitro with the substituting group in 1 ~ 2 substituent phenyl, when phenyl is monosubstituted, substituting group be 2 replacements, 3 replace or 4 replacements; When phenyl is two replacement, substituting group is 2,4 two replacements.
The present invention also aims to the preparation method that the above-mentioned phosphate compound containing 1,2,3-triazoles ring is provided.
Shown in a kind of formula (I), the preparation method of Compound C AU2014-JY, comprises the steps:
(1) by compound formula (II) Suo Shi by with sodium azide generation substitution reaction, obtain falling nitrogen compound shown in formula III;
(2) will nitrogen compound be fallen shown in formula III and replace compound shown in alkine compounds formula IV generation click-reaction production (V);
(3) formula (V) and carboxylic acid compound formula VI esterification are generated formula I.
In above-mentioned preparation method:
Also add ammonium chloride in the reaction of step (1), react in a solvent, the mixed solvent of the optional methyl alcohol of solvent and water, wherein methyl alcohol: the volume ratio of water is 2:1 ~ 1:2, and optimum proportion is 1:1; Temperature of reaction is-10 DEG C ~ 40 DEG C, and best anti-temperature is room temperature 25 DEG C, and the reaction times is 5 ~ 12 hours;
Wherein, the mol ratio of compound shown in formula II and sodium azide is 1:1.0 ~ 2.5, and optimum mole ratio is 1:2; The mol ratio of compound shown in formula II and ammonium chloride is 1:1.0 ~ 3, and optimum mole ratio is 1:2.
Step also adds catalyzer sodium ascorbate and copper sulfate in (2), and solvent for use is the mixed solvent of methyl alcohol and water, wherein methyl alcohol: the volume ratio of water is 2:1 ~ 1:2, and optimum proportion is 1:1; Temperature of reaction is-10 DEG C ~ 40 DEG C, and best anti-temperature is room temperature 25 DEG C, and the reaction times is 5 ~ 12 hours;
Wherein, the mol ratio replacing alkine compounds shown in compound shown in formula III and formula IV is 1:0.8 ~ 2.5, and optimum response mol ratio is 1:1.1; The mol ratio of compound shown in formula III and catalyzer sodium ascorbate is 1:0.01 ~ 0.5, and optimum mole ratio is 1:0.1; The mol ratio of compound shown in formula III and catalyst sulfuric acid copper is 1:0.01 ~ 2.5, and optimum mole ratio is 1:0.1.
Step also adds condensing agent and catalyzer in (3), and temperature of reaction is-10 DEG C ~ 40 DEG C, and optimal reaction temperature is room temperature 25 DEG C, and the reaction times is 5 ~ 12 hours; Described condensing agent is dicyclohexylcarbodiimide, and described catalyzer is DMAP;
Wherein, shown in compound and formula VI shown in formula (V), the mol ratio of carboxylic acid compound is 1:1.0 ~ 2.0; Shown in formula (V), the mol ratio of compound and condensing agent dicyclohexylcarbodiimide (DCC) is 1:0.5 ~ 5, and optimum mole ratio is 1:1.5; The mol ratio of compound shown in formula III and catalyzer DMAP (DMAP) is 1:0.01 ~ 0.5, and optimum mole ratio is 1:0.1.
The present invention also aims to provide a plant growth regulators, its activeconstituents is the phosphate compound containing 1,2,3-triazoles ring shown in formula (I) or its pharmacy acceptable salt.
The present invention also aims to provide a kind of herbicide, its activeconstituents is the phosphate compound containing 1,2,3-triazoles ring shown in formula (I) or its pharmacy acceptable salt.
Described plant-growth regulator or herbicide are be pharmaceutically pharmaceutically acceptable formulation, such as: missible oil, wettable powder, suspension agent, pulvis, soluble powder, aqua, water dispersible granules, fumicants, granule, seed coat agent etc.
The present invention also aims to provide compound shown in formula I or its pharmacy acceptable salt is preparing the application in plant-growth regulator or coordinate plant growth.
In described application, the following at least one performance of described plant-growth regulator regulating plant:
1) plant-growth is delayed;
2) cane is suppressed to extend;
3) plant internode is shortened;
4) plant stress-resistance performance is improved, as improved plant lodging resistance;
Described plant is paddy rice, rape or corn.
Object of the present invention also there are provided the phosphate compound (CAU2014-JY) containing 1,2,3-triazoles ring shown in formula I or its pharmacy acceptable salt is being prepared herbicide or killed the application in weeds.
Described weeds are Herba Eleusines Indicae, barnyard grass, Horseweed Herb, cogongrass, amur foxtail, Bermuda grass, Herba Setariae Viridis, Sorghum halepense, Herba Clinopodii Polycephali or Semen Euphorbiae.
The preparation method of the phosphate compound containing 1,2,3-triazoles ring of the present invention, raw material is cheap and easy to get, and reaction scheme is simple, and the described phosphate compound weeding activity containing 1,2,3-triazoles ring is better.Weeding activity Plating measurement result shows, have very strong restraining effect to the root of wheat and rape, Stem nematode, potted plant experiment shows, has good Developing restraint effect to barnyard grass.Phosphate compound containing 1,2,3-triazoles ring of the present invention has high plant growth regulating activity when lower concentration and has weeding activity concurrently.
Accompanying drawing explanation
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of Compound C AU2014-JY-A3.
Fig. 2 is the carbon-13 nmr spectra figure of Compound C AU2014-JY-A3.
Fig. 3 is the nucleus magnetic resonance phosphorus spectrogram of Compound C AU2014-JY-A3.
Fig. 4 is that Compound C AU2014-JY-A3, CAU2014-JY-B4 are to weeding pot experiment barnyard grass picture.
Embodiment
Below by specific embodiment, the present invention will be described.
Experimental technique described in following embodiment, if no special instructions, is ordinary method; Described reagent and material, if no special instructions, all can obtain from commercial channels.
Embodiment 1 Compound C AU2014-JY-A3, (R
1for phenyl, R
2for menaphthyl) preparation and Structural Identification.
(1) in the round-bottomed flask of 100ml, 1.65g (10mmol) intermediate is added successively, compound shown in formula II, 30mL methyl alcohol: water 1:1 solution, ammonium chloride 1.06g (20mmol), sodium azide 1.30g (20mmol) is added, room temperature for overnight after dissolving.After having reacted, extract three times by methylene dichloride-aqueous systems, get organic phase, add anhydrous sodium sulphate, hold over night, except the thick product of the compound obtaining structure shown in formula III after desolventizing.
(2) compound shown in products therefrom and formula III is without the need to purifying in (1) more than, directly be dissolved in 30mL methyl alcohol: in water 1:1 solution, add sodium ascorbate 0.2g (1mmol) successively, phenylacetylene (11mmol), cupric sulfate pentahydrate 0.16g (1mmol), stirring at room temperature, reaction is spent the night.After having reacted, extract three times by methylene dichloride-aqueous systems, get organic phase, add anhydrous sodium sulfate drying, hold over night, concentrated, silicagel column obtains white solid after being separated crude product, is 1,2,3-triazole compounds, i.e. compound shown in formula (V), two-step reaction productive rate is 60%.
(3) 1,2,3-triazoles compound 5mmol shown in modus ponens (V) is dissolved in 20mL methylene dichloride, adds DCC 1.03g, stirring at room temperature one hour.Separately get intermediate (IV) 4mmol to be dissolved in 20mL methylene dichloride, add DMAP 0.06g (0.5mmol), under ice bath, add system, stir 10 minutes, react under then system being placed in room temperature and spend the night.After having reacted, system suction filtration is got filtrate, be separated with silicagel column and obtain the CAU2014-JY-A3 of target product shown in formula I, productive rate is 90%.
CAU2014-JY-A3 structural identification data, are shown in Fig. 1-3.
1H?NMR(300MHz,CDCl3)δ：1.27(t,J＝7.1Hz,6H),1.98-2.10(m,2H),4.01-4.11(m,6H),4.55(d,J＝4.6Hz,2H),5.49-5.53(m,1H),7.17(s,1H),7.29-7.40(m,8H),7.62-7.74(m,4H),7.86-7.89(m,1H)；13C?NMR(75.5MHz,CDCl3)δ:15.91(d,JC-P＝5.7Hz),27.58(d,JC-P＝141.0Hz),38.52,52.04(d,JC-P＝8.1Hz),61.68(d,JC-P＝4.4Hz),61.77(d,JC-P＝4.3Hz),67.45,120.22,123.09,124.96,125.34,125.44,126.09,127.61,127.81,128.21,128.28,129.33,129.95,131.42,131.56,133.21,147.13,169.69；31P?NMR(121.5MHz,CDCl3)δ:25.49。
Other general formulas are that the series compound of CAU2014-JY prepares all according to the method described above.Their compound number, R
1, R
2the substituted radical that group is corresponding, high resolution mass spectrum data, outward appearance and yield are in table 1, and the proton nmr spectra of Structural Identification, carbon spectrum, phosphorus modal data are in table 2.
Table 1 general formula is the numbering of the series compound of CAU2014-JY, substituted radical, high resolution mass spectrum data, outward appearance and yield (wherein, Et is ethyl)
Table 2 general formula is nuclear-magnetism carbon spectrum, hydrogen spectrum, the phosphorus modal data of the series compound of CAU2014-JY
The preparation of embodiment 2, Compound C AU2014-JY-A3 missible oil (5%)
In 100mL volumetric flask, add Compound C AU2014-JY-A35g, agriculture breast 0203B 15g, penetrating agent JFC-10.6g, then obtains with solvent toluene constant volume the missible oil that content is 5%.
Other general formulas are that the missible oil of CAU2014-JY compound all can prepare according to the method described above.
Embodiment 3 general formula be the compound of CAU2014-JY delay plant-growth determination of activity
Test, with reference to gibberellin biological method for measuring, adopts rice leaf sheath point sample method to carry out.Rice varieties is Japan fine (Oryza sativa L.japonica.cv.Nipponbare, genetic breeding system of China Agricultural University).
Seed is transferred in the beaker filling 1% agar through seed soaking, vernalization after cultivating, (now seedling height about 1cm) when about about 2mm is stretched out from the imperfect leaf of first in first intact leaves top is cultured in illumination box, use the series concentration liquid of microsyringe drop 1.0 μ L between the first imperfect blade and the first intact leaves (by a small amount of dissolve with methanol of compound prepared by embodiment 1, carry out dilution with the distilled water containing 1% tween-80 to obtain), take paclobutrazol as contrast medicament, not contain the distilled water of medicament for blank.Seedling after process moves in illumination box and cultivates, by the length measuring seedling second leaf sheath after 3d, data Excel2007 software processes, the second leaf sheath length inhibiting rate and log concentration carry out linear regression, drug concentration IC corresponding during the elongation suppression 20% of calculating leaf sheath
20, determination of activity result is as shown in table 4.
Table 4CAU2014-JY series compound is to delaying rice leaf sheath growth activity (mg/L)
| Compound | IC20 | Compound | IC20 |
| Paclobutrazol | 119 | Uniconazole | 55 |
| CAU2014-JY-A1 | 225 | CAU2014-JY-C1 | >1000 |
| CAU2014-JY-A2 | 483 | CAU2014-JY-C2 | 150 |
| CAU2014-JY-A3 | 36 | CAU2014-JY-C3 | 32 |
| CAU2014-JY-A4 | 352 | CAU2014-JY-C4 | 229 |
| CAU2014-JY-A5 | >1000 | CAU2014-JY-C5 | 921 |
| CAU2014-JY-A6 | 241 | —— | —— |
| CAU2014-JY-A7 | 31 | CAU2014-JY-C7 | 23 |
| CAU2014-JY-A8 | 767 | CAU2014-JY-C8 | >1000 |
| CAU2014-JY-B1 | 356 | CAU2014-JY-D1 | 240 |
| CAU2014-JY-B2 | >1000 | CAU2014-JY-D2 | 655 |
| CAU2014-JY-B3 | 57 | CAU2014-JY-D3 | 39 |
| CAU2014-JY-B4 | 415 | CAU2014-JY-D4 | 671 |
| CAU2014-JY-B5 | 197 | CAU2014-JY-D5 | 216 |
| CAU2014-JY-B6 | 196 | —— | —— |
| CAU2014-JY-B7 | 63 | CAU2014-JY-D7 | 59 |
| CAU2014-JY-B8 | 854 | CAU2014-JY-D8 | 657 |
Can be learnt by the data in table 4, test compound is except CAU2014-JY-A5, CAU2014-JY-B2, CAU2014-JY-C1 and CAU2014-JY-C8 do not show obvious retarding of growing effect, all the other test compounds all show rice seedling leaf sheath delayed growth effect, and wherein Compound C AU2014-JY-A3, CAU2014-JY-A7, CAU2014-JY-B3, CAU2014-JY-B7, CAU2014-JY-C3, CAU2014-JY-C7, CAU2014-JY-D3 and CAU2014-JY-D7 eight kinds of medicament postponed effects are better than contrast medicament uniconazole and paclobutrazol.
Embodiment 4 eight kinds of new medicaments control growth test result to rice seedling
Target compound is prepared into 5% missible oil (its composition is with the missible oil in embodiment 2) and carries out field test, determine that its delayed growth is active further.
Rice varieties is Japan fine (Oryza sativa L.japonica.cv.Nipponbare, genetic breeding system of China Agricultural University is so kind as to give).
When field growing to 1 leaf 1 heart, 8 kind of 5% missible oil, the 1000 times of diluents getting above-mentioned preparation carry out foliar spray, with 5% uniconazole wettable powder, 1000 times of diluents and the 500 times of diluent contrasts of 15% paclobutrazol wettable powder, and establish clear water to contrast.Process latter 14 days, sampling survey Plant Height of Rice and tiller number.Determination of activity result is as shown in table 5.
Table 5CAU2014-JY series compound new medicament controls rice seedling growth result
Can be learnt by the data in table 5, reagent agent prepared by the present invention all shows certain delayed growth effect to rice seedling, promotes the generation of tillering simultaneously.Compound C AU2014-JY-A7, CAU2014-JY-B3, CAU2014-JY-B7, CAU2014-JY-C7, CAU2014-JY-D3 and CAU2014-JY-D7 six kinds of medicament postponed effects are better than contrast medicament uniconazole and paclobutrazol, are better than contrast medicament or with to contrast medicament suitable to the control of plant height.
Embodiment 5 eight kinds of new medicaments control growth test result to corn
Target compound is prepared into 5% missible oil (its composition is with the missible oil in embodiment 2) and carries out corn control growth field test, determine that its delayed growth is active further.
Corn variety is No. 5 (Zea mays L., purchased from the Jin Hai Zhong Ye company limited of Laizhou City) in gold sea.
When grown in field is to the jointing initial stage, 8 kind of 5% missible oil, the 1000 times of diluents getting above-mentioned preparation carry out foliar spray, with 5% uniconazole wettable powder, 1000 times of diluents and the 500 times of diluent contrasts of 15% paclobutrazol wettable powder, and establish clear water to contrast.During harvest corn, sampling survey plant height and Ear height.Determination of activity result is as shown in table 6.
Table 6CAU2014-JY series compound new medicament regulating corn growth result
Data in table 6 can be learnt, reagent agent prepared by the present invention controls corn base portion 1-2 and saves internode elongation, and be all better than contrasting medicament to the control of plant height, these effects contribute to preventing corn lodging.
Embodiment 6 general formula is that the compound of CAU2014-JY is to the mensuration of the preliminary weeding activity of barnyard grass
Choosing barnyard grass respectively as test plant, adopt Plating, take acetochlor as contrast medicament, and the long and long size judging medicament virulence of stem with the root of barnyard grass, determination of activity result is as shown in table 7.In table, A1 represents CAU2014-JY-A1, and other by that analogy.
Table 7 Compound C AU2014-JY is to the preliminary Herbicidal of barnyard grass
Primary dcreening operation data in table 7 can be learnt, reagent agent prepared by the present invention has good weeding activity to barnyard grass, and especially Compound C AU2014-JY-A3, CAU2014-JY-B1, CAU2014-JY-B2, CAU2014-JY-B3, CAU2014-JY-B4, CAU2014-JY-C2, CAU2014-JY-C3 and CAU2014-JY-D3 are better than contrast medicament acetochlor.
Embodiment 7 Compound C AU2014-JY is to the potted plant Herbicidal of barnyard grass.
Choose barnyard grass as test plant, acetochlor is medicament in contrast, adopts pot-culture method, and select active 8 kinds of best compounds in Compound C AU2014-JY, 4 kinds of concentration, seedling aftertreatment, judges the size of medicament virulence with the fresh weight of barnyard grass.General formula be the compound of CAU2014-JY to the inhibit activities of barnyard grass in table 8.
Table 8 Compound C AU2014-JY is to the potted plant Herbicidal of barnyard grass
Potted plant data in table 8 can be learnt, reagent agent prepared by the present invention has good weeding activity to barnyard grass, especially Compound C AU2014-JY-B1 and CAU2014-JY-C3 is under the spraying medicine concentration of 62.5g/ha, is better than contrast medicament acetochlor to the barnyard grass effect of preventing and kill off.
Claims (13)
1. the phosphate compound containing 1,2,3-triazoles ring or its pharmacy acceptable salt, the structural formula of the described phosphate compound containing 1,2,3-triazoles ring is such as formula shown in (I);
In formula (I),
R
1for the phenyl of ethoxycarbonyl, chloromethyl, the tertiary butyl, phenyl or replacement, the substituting group on the phenyl of described replacement is any one halogen, substituting group be 2 replacements, 3 replace or 4 replacements;
R
2for methyl, 2-chloropyridine base, menaphthyl or with 1 ~ 2 substituent phenyl, described is halogen or nitro with the substituting group in 1 ~ 2 substituent phenyl, when phenyl is monosubstituted, substituting group be 2 replacements, 3 replace or 4 replacements; When phenyl is two replacement, substituting group is 2,4 two replacements.
2. the preparation method of the phosphate compound containing 1,2,3-triazoles ring described in claim 1, is characterized in that, comprise the steps:
(1) by compound shown in formula II by with sodium azide generation substitution reaction, obtain falling nitrogen compound shown in formula III;
(2) compound shown in alkine compounds generation click-reaction production (V) is replaced by falling shown in formula III shown in nitrogen compound and formula IV;
(3) carboxylic acid compound esterification shown in formula (V) Yu formula VI is generated formula I.
3. preparation method according to claim 2, is characterized in that, step also adds ammonium chloride in (1), and wherein the mol ratio of compound shown in formula II and sodium azide is 1:1.0 ~ 2.5; The mol ratio of compound shown in formula II and ammonium chloride is 1:1.0 ~ 3; Temperature of reaction is-10 DEG C ~ 40 DEG C; Reaction times is 5 ~ 12 hours.
4. preparation method according to claim 2, is characterized in that, step also adds catalyzer sodium ascorbate and copper sulfate in (2); Temperature of reaction is-10 DEG C ~ 40 DEG C, and the reaction times is 5 ~ 12 hours; Wherein, the mol ratio replacing alkine compounds shown in compound shown in formula III and formula IV is 1:0.8 ~ 2.5; The mol ratio of compound shown in formula III and sodium ascorbate is 1:0.01 ~ 0.5; The mol ratio of compound shown in formula III and copper sulfate is 1:0.01 ~ 2.5.
5. preparation method according to claim 2, is characterized in that, step also adds condensing agent and catalyzer in (3); Temperature of reaction is-10 DEG C ~ 40 DEG C, and the reaction times is 5 ~ 12 hours; Wherein, shown in compound and formula VI shown in formula (V), the mol ratio of carboxylic acid compound is 1:1.0 ~ 2.0.
6. preparation method according to claim 5, is characterized in that, described condensing agent is dicyclohexylcarbodiimide, and described catalyzer is DMAP; Wherein, the mol ratio of compound shown in formula (V) and condensing agent is 1:0.5 ~ 5; Shown in formula (V), the mol ratio of compound and catalyzer is 1:0.01 ~ 0.5.
7. a plant growth regulators, its activeconstituents is the phosphate compound or its pharmacy acceptable salt that contain 1,2,3-triazoles ring according to claim 1.
8. a herbicide, its activeconstituents is the phosphate compound or its pharmacy acceptable salt that contain 1,2,3-triazoles ring according to claim 1.
9. phosphate compound containing 1,2,3-triazoles ring according to claim 1 or its pharmacy acceptable salt are preparing the application in plant-growth regulator or coordinate plant growth.
10. application according to claim 9, is characterized in that, described coordinate plant growth is following at least one performance:
1) plant-growth is delayed;
2) cane is suppressed to extend;
3) plant internode is shortened;
4) plant stress-resistance performance is improved.
11. application according to claim 9, is characterized in that, described plant is paddy rice, rape or corn.
12. phosphate compounds containing 1,2,3-triazoles ring according to claim 1 or its pharmacy acceptable salt are being prepared herbicide or are being killed the application in weeds.
13. application according to claim 12, is characterized in that, described weeds are Herba Eleusines Indicae, barnyard grass, Horseweed Herb, cogongrass, amur foxtail, Bermuda grass, Herba Setariae Viridis, Sorghum halepense, Herba Clinopodii Polycephali or Semen Euphorbiae.
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| CN106719820A (en) * | 2016-12-26 | 2017-05-31 | 东莞市联洲知识产权运营管理有限公司 | A kind of agricultural bactericidal composition containing triazole bactericidal agent and preparation method thereof |
| CN108558945A (en) * | 2018-05-04 | 2018-09-21 | 大连理工大学 | The method that the trisubstituted 1,2,3- triazoles of 4- phosphoryls -1,4,5- are prepared in water phase or Biomedia |
| CN109265681A (en) * | 2018-08-29 | 2019-01-25 | 华南理工大学 | Copper ion liquid catalyst prepares the method for 1,4- stereoregular polytriazoles, 1,4- stereoregular polytriazoles and its application |
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| GLOWACKA, IWONA E.ET AL: "Synthesis of novel 1-hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates", 《PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS》 * |
| 余治华等: "含吡啶（或噻唑）和1,2,3-三唑双杂环的a -氨基膦酸酯衍生物的合成与除草活性", 《华中师范大学学报（自然科学版）》 * |
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| CN106719820A (en) * | 2016-12-26 | 2017-05-31 | 东莞市联洲知识产权运营管理有限公司 | A kind of agricultural bactericidal composition containing triazole bactericidal agent and preparation method thereof |
| CN108558945A (en) * | 2018-05-04 | 2018-09-21 | 大连理工大学 | The method that the trisubstituted 1,2,3- triazoles of 4- phosphoryls -1,4,5- are prepared in water phase or Biomedia |
| CN109265681A (en) * | 2018-08-29 | 2019-01-25 | 华南理工大学 | Copper ion liquid catalyst prepares the method for 1,4- stereoregular polytriazoles, 1,4- stereoregular polytriazoles and its application |
| CN109265681B (en) * | 2018-08-29 | 2021-05-14 | 华南理工大学 | Method for preparing 1, 4-stereoregular polytriazole under catalysis of copper ion liquid, 1, 4-stereoregular polytriazole and application thereof |
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| Publication number | Publication date |
|---|---|
| CN104311598B (en) | 2016-06-01 |
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