CN113336776B - Plant growth promoter and its synthesis and application - Google Patents

Plant growth promoter and its synthesis and application Download PDF

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CN113336776B
CN113336776B CN202110601972.6A CN202110601972A CN113336776B CN 113336776 B CN113336776 B CN 113336776B CN 202110601972 A CN202110601972 A CN 202110601972A CN 113336776 B CN113336776 B CN 113336776B
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丁其春
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Zhangzhou Health Vocational College
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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Abstract

The invention discloses a plant growth promoter and a synthetic method and application thereof. Preparation of 3-methyl-4 amino-5-mercapto-4HThe target compound is prepared by reacting the triazole with substituted aromatic aldehyde and halogenated aryl ketone in one step. By testing the plant growth regulating activity of the obtained 10 compounds, all the compounds have obvious growth promoting effect on the growth of plants, and the growth promoting effect on radicle is basically generally stronger than the effect on stem. The compound synthesized by the invention can be used in the agricultural field as a powerful growth promoter for crops.

Description

Plant growth promoter and its synthesis and application
Technical Field
The invention belongs to the field of agriculture, and particularly relates to a plant growth promoter, a synthesis method and application thereof.
Background
In recent decades, 1,2, 4-triazole [3,4-b ] [1,3,4] thiadiazines have been widely studied at home and abroad because of their wide and important biological activities, but have very little research on 1,2, 4-triazolothiazines containing aroyl groups at the 7-position, namely 3, 6-disubstituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines and their biological activity-related relations, and the compounds are reported to have certain anticancer and bactericidal effects by a small number of documents at present, which has very important significance for the development and development of new drugs.
Disclosure of Invention
The invention aims to provide a plant growth promoter, and a synthesis method and application thereof.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the synthesis method of the 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines comprises the following steps: 30mL of absolute ethyl alcohol, 1mL of triethylamine (alkaline condition) and 0.001mol of 3-methyl-4-amino-5-mercapto-4H-1, 2, 4-triazole are added into a small 50mL flask to react with equimolar substituted aromatic aldehyde under reflux condition (115-120 ℃), TLC tracking is carried out, after the reaction is finished, equimolar halogenated aromatic ethanone is added, finally solvent is removed by rotary evaporation, and the target product is prepared by column chromatography.
The synthetic route is as follows:
the substituents of the substituted aromatic aldehyde and the halogenated aryl ethanone are respectively shown as above, and the obtained 10 compounds are sequentially:
no. 1: 3-methyl-6-phenyl-7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 2: 3-methyl-6-phenyl-7- (4-methoxybenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 3: 3-methyl-6- (3-chlorophenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 4: 3-methyl-6- (3-chlorophenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 5: 3-methyl-6-phenyl-7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 6: 3-methyl-6- (4-methoxyphenyl) -7- (4-methoxybenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
No. 7: 3-methyl-6- (4-methoxyphenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 8: 3-methyl-6- (4-methoxyphenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
No. 9: 3-methyl-6- (4-hydroxyphenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
Number 10: 3-methyl-6- (4-hydroxyphenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine.
According to the technical scheme, the 3-methyl-4 amino-5-mercapto-4H-homotriazole is prepared, and then reacts with substituted aromatic aldehyde and halogenated aryl ethanone to prepare the target compound in one step. The compound can be used in the agricultural field and used as a powerful growth promoter for crops. By testing the plant growth regulating activity of the obtained 10 novel compounds, all the compounds have obvious growth promoting effect on plants, the growth promoting effect on radishes and stems of dicotyledonous plants (radishes) is generally obviously stronger than that of monocotyledonous plants (wheat), and the growth promoting effect on radishes is basically generally stronger than that of stems. Wherein, the compounds with the highest growth promotion effect on dicotyledon (radish) radicle and stem are respectively compound No. 1, and the content of the compounds reaches 390 percent and 145 percent respectively at 20 ppm; the compound 6 with the highest growth promotion effect on monocot plant (wheat) radicle reaches 108% at 50ppm, while the compound 8 with the highest growth promotion effect on its stem reaches 199% at 50 ppm; but the most surprising is that the compound No. 8 has obvious growth promoting effect on radicle and stem of monocotyledonous and dicotyledonous plants (wheat and radish), and the highest promoting rate can reach about 200%.
The synthesis method has the advantages that: (1) The synthesis of the compound is completed by adopting a one-pot method, and the process is simple and convenient; (2) The whole system is alkaline, and triethylamine serving as a catalyst can catalyze the two-stage reaction; in addition, the whole process adopts alkaline triethylamine for catalysis, because the 2 nd stage is required to be carried out under alkaline conditions, if the 1 st stage system is acidic, the pH value is regulated to be alkaline again when the 2 nd stage is reached, so that the operation is inconvenient, and impurities are introduced. (3) Triethylamine is a liquid and is easily removed by rotary evaporation.
Drawings
FIG. 1 is a trans-form of the structure of Compound No. 4.
Detailed Description
The present invention will be described in detail with reference to the following specific embodiments.
Example 1
Synthetic route and method of 3, 6-disubstituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines
The synthesis method comprises the following steps: 30mL of absolute ethyl alcohol, 1mL of triethylamine, 0.001mol of 3-methyl-4-amino-5-mercapto-4H-1, 2, 4-triazole and equimolar substituted aromatic aldehyde are added into a small 50mL flask, the mixture is reacted under reflux (115-120 ℃) and tracked by TLC, after the reaction is finished, equimolar halogenated aromatic ethanone is added, finally solvent is removed by rotary evaporation, and a target product is prepared by column chromatography.
The synthetic route is as follows:
the substituents of the substituted aromatic aldehyde and the halogenated aryl ethanone are shown as above, and 10 compounds are obtained in turn: no. 1: 3-methyl-6-phenyl-7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:75％.M.p.:193-195℃.IR(cm -1 ):3423,3062,2966,1677,1631,702. 1 H NMR(500MHz,DMSO-d 6 )δ:2.34(s,3H),5.05(t,J＝5.8Hz,1H),5.76 (d,J＝5.2Hz,1H),7.04(d,J＝6.7Hz,1H),7.28(t,J＝7.2Hz,1H), 7.34(t,J＝7.6Hz,2H),7.50(d,J＝7.6Hz,2H),7.58(t,J＝7.8Hz, 2H),7.71(t,J＝7.4Hz,1H),8.06(d,J＝7.5Hz,2H)； 13 C NMR(125MHz, DMSO-d 6 )δ:10.15,42.67,57.83,127.71,128.46,129.02,129.30,129.56, 134.72,134.96,137.61,139.80,150.92,195.68.
No. 2: 3-methyl-6-phenyl-7- (4-methoxybenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:80％.M.p.:212-214℃.IR(cm -1 ):3415,2978,2839,1672,1598,694. 1 H NMR(500MHz,DMSO-d 6 )δ:2.33(s,3H),3.87(s,3H),4.97(t,J＝6.3 Hz,1H),5.71(d,J＝5.6Hz,1H),7.00(d,J＝7.2Hz,1H),7.09(d,J ＝8.8Hz,2H),7.27(t,J＝7.2Hz,1H),7.33(t,J＝7.4Hz,2H),7.49(d,J＝7.6Hz,2H),8.03(d,J＝8.8Hz,2H). 13 C NMR(125MHz,DMSO-d 6 ) δ:10.14,42.32,56.21,58.30,114.84,127.68,127.78,128.46,129.00,131.77,137.62,140.02,150.87,164.49,193.90.
No. 3: 3-methyl-6- (3-chlorophenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:84％.M.p.:203-205℃.IR(cm -1 ):3427,3053,2927,1678,1595, 775,686. 1 H NMR(500MHz,DMSO-d 6 )δ:2.35(s,3H),5.16(t,J＝5.2Hz, 1H),5.78(d,J＝4.5Hz,1H),7.13(d,J＝6.1Hz,1H),7.35-7.39(m, 2H),7.46(d,J＝7.1Hz,1H)；7.60(t,J＝7.6Hz,2H),7.65(s,1H),7.72(t,J＝7.4Hz,1H),8.10(d,J＝7.9Hz,2H)； 13 C NMR(125MHz,DMSO-d 6 ) δ:10.15,41.90,56.70,126.40,127.69,128.42,129.42,129.50,130.90,133.71,134.71,134.85,139.42,140.18,150.86,195.58.
No. 4: 3-methyl-6- (3-chlorophenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:78％.M.p.:191-193℃.IR(cm -1 ):3392,3076,2916,1705,1585, 756,698. 1 H NMR(500MHz,DMSO-d 6 )δ:2.36(s,3H),5.15(t,J＝5.7Hz, 1H),5.56(d,J＝4.8Hz,1H),7.13(d,J＝6.5Hz,1H),7.35-7.39(m, 3H),7.55(s,1H),7.58(dd,J 1 ＝1.9Hz,J 2 ＝8.4Hz,1H),7.77(d,J＝ 1.9Hz,1H),7.79(d,J＝8.5Hz,1H)； 13 C NMR(125MHz,DMSO-d 6 )δ:10.17, 46.56,56.76,126.34,127.59,128.01,128.55,130.58,130.94,131.79,132.96,133.74,135.57,137.58,139.16,139.69,150.86,196.35.
No. 5: 3-methyl-6-phenyl-7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:86％.M.p.:165-167℃.IR(cm -1 ):3396,3051,2916,1705,1583, 763,694. 1 H NMR(500MHz,DMSO-d 6 )δ:2.35(s,3H),5.03(t,J＝6.2Hz, 1H),5.53(d,J＝5.3Hz,1H),7.06(d,J＝7Hz,1H),7.28(t,J＝7Hz, 1H),7.34(t,J＝6.9Hz,2H),7.43(d,J＝7.4Hz,2H),7.54(dd,J 1 ＝ 1.8Hz,J 2 ＝8.4Hz,1H),7.63(d,J＝8.4Hz,1H),7.76(d,J＝1.7Hz, 1H)； 13 C NMR(125MHz,DMSO-d 6 )δ:10.17,47.33,58.04,127.30,127.62, 128.07,129.09,130.54,131.70,132.54,135.79,137.09,137.56,139.45, 151.02,196.75.
No. 6: 3-methyl-6- (4-methoxyphenyl) -7- (4-methoxybenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:84％.M.p.:187-189℃.IR(cm -1 ):3400,2997,2937,1666,1597, 700. 1 H NMR(500MHz,DMSO-d 6 )δ:2.32(s,3H),3.71(s,3H),3.87(s,3H), 4.87(t,J＝6.7Hz,1H),5.69(d,J＝5.9Hz,1H),6.89(d,J＝8.7Hz, 2H),6.93(d,J＝7.5Hz,1H),7.10(d,J＝8.8Hz,2H),7.42(d,J＝8.6Hz,2H),8.02(d,J＝8.8Hz,2H)； 13 C NMR(125MHz,DMSO-d 6 )δ:10.12, 42.44,55.53,56.21,58.10,114.35,114.86,127.74,129.10,129.41,131.73,140.15,150.91,159.34,164.50,193.87.
No. 7: 3-methyl-6- (4-methoxyphenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:82％.M.p.:184-186℃.IR(cm -1 ):3410,3068,2947,1654,1612, 692. 1 H NMR(500MHz,DMSO-d 6 )δ:2.39(s,3H),3.66(s,3H),4.92(dd, J 1 ＝1.7Hz,J 2 ＝11Hz,1H),5.77(d,J＝2.4Hz,1H),6.82(d,J＝8.7 Hz,2H),7.16(d,J＝11Hz,1H),7.27(d,J＝8.6Hz,2H),7.48(t,J ＝7.7Hz,2H),7.63(t,J＝7.4Hz,1H),7.86(d,J＝7.7Hz,2H)； 13 C NMR (125MHz,DMSO-d 6 )δ:10.28,40.56,55.53,59.31,114.23,128.47,128.64, 128.91,129.41,134.60,135.77,139.05,150.59,159.24,197.25.
No. 8: 3-methyl-6- (4-methoxyphenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:80％.M.p.:186-188℃.IR(cm -1 ):3431,3070,2924,1701,1606, 752,694. 1 H NMR(500MHz,DMSO-d 6 )δ:2.33(s,3H),3.71(s,3H),4.90(t, J＝6.5Hz,1H),5.49(d,J＝5.7Hz,1H),6.86(d,J＝8.7Hz,2H),6.97 (d,J＝7.4Hz,1H),7.33(d,J＝8.7Hz,2H),7.53(dd,J 1 ＝1.7Hz,J 2 ＝8.4Hz,1H),7.57(d,J＝8.4Hz,1H),7.76(d,J＝1.7Hz,1H)； 13 C NMR (125MHz,DMSO-d 6 )δ:10.13,47.71,55.61,58.01,114.45,128.55,128.97, 130.49,131.66,132.96,135.32,135.88,137.52,139.95,151.07,159.05, 196.84.
No. 9: 3-methyl-6- (4-hydroxyphenyl) -7-benzoyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:78％.M.p.:187-189℃.IR(cm -1 ):3425,3254,3005,2910,1682, 1612,686. 1 H NMR(500MHz,DMSO-d 6 )δ:2.33(s,3H),4.86(t,J＝8.0Hz, 1H),5.72(d,J＝7.1Hz,1H),6.71(d,J＝10.7Hz,2H),6.92(d,J＝ 9.2Hz,1H),7.31(d,J＝10.7Hz,2H),7.58(t,J＝9.7Hz,2H),7.70(t,J＝9.2Hz,1H),8.02(d,J＝9.3Hz,2H),9.52(s,1H)； 13 C NMR(125 MHz,DMSO-d 6 )δ:10.13,43.09,58.13,115.75,127.52,129.05,129.20, 129.55,134.71,135.03,140.19,151.02,157.61,195.65.
Number 10: 3-methyl-6- (4-hydroxyphenyl) -7- (2, 4-dichlorobenzoyl) -6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazine
Yield:80％.M.p.:200-202℃.IR(cm -1 ):3410,3240,3015,2895,1688, 1612,771,694. 1 H NMR(500MHz,DMSO-d 6 )δ:2.32(s,3H),4.79(t,J＝ 8.7Hz,1H),5.46(d,J＝7.6Hz,1H),6.69(d,J＝10.8Hz,2H),6.93 (d,J＝9.8Hz,1H),7.21(d,J＝10.8Hz,2H),7.47(dd,J 1 ＝2.3Hz, J 2 ＝10.6Hz,1H),7.60(d,J＝10.6Hz,1H),7.75(s,1H),9.55(s, 1H)； 13 C NMR(125MHz,DMSO-d 6 )δ:10.12,48.04,58.73,115.81,128.05, 129.04,130.48,131.59,132.38,135.30,135.97,137.56,139.91,151.13, 157.24,196.94.
Wherein, the structure diagram of the trans isomer of the compound No. 4 is shown in fig. 1, the crystal structure and data of the trans isomer structure of the compound No. 4 are shown in table 1, and the bond length and bond angle of the trans isomer structure of the compound No. 4 are shown in table 2.
Table 1.4 Crystal Structure and data of Trans Structure of Compound
Table 2 4 bond lengths and bond angles for the trans-structures of Compounds No. 2 4
Example 2
Application of 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines in plant growth regulation
1. The tested plant seeds were: wheat seeds (monocots) and radish seeds (dicots).
2. The experimental method comprises the following steps:
1) 5mg of the sample was weighed using an electronic balance, dissolved by adding a small amount of ethanol, and diluted to 20ppm, 50ppm, 100ppm of the pharmacological solution.
2) Selecting proper amount of full and similar seeds, washing with distilled water four times, and soaking at room temperature for 3 hr.
3) 2 layers of filter paper were spread on 9 cm diameter petri dishes, each with 20 of the above described wheat or radish seeds placed therein. 10ml of each of the above 20ppm, 50ppm and 100ppm of the drug solution was measured and poured into the above dish. In addition, 10ml of distilled water added with a small amount of ethanol was directly poured into the culture dish to perform a blank comparison experiment.
4) The culture dish is covered, and the culture is carried out at the constant temperature of 25 ℃, and a certain amount of distilled water can be added at regular time during the culture process so as to prevent the drying out in the culture dish.
5) After 5 days, checking the germination and growth conditions of seeds, selecting 10 plants with the best growth in each culture dish, calculating the length of stems and roots, and taking an average value.
3. Calculation method
Calculating plant growth regulating effect
And selecting 10 plants with the best growth in each culture dish, calculating the stem length and root length, taking an average value, comparing with a blank experiment, evaluating the drug effect, and carrying out positive expression promotion and negative expression inhibition on the result, thereby having weeding performance. The calculation method comprises the following steps:
effect = [ (average length of test plants-average length of blank experiments)/average length of blank experiments ] ×100% positive value indicates that the effect of promoting growth is stronger as the number is larger; negative values indicate a growth inhibitory effect, and smaller numbers indicate a stronger growth inhibitory effect.
4. Test results:
TABLE 3 plant growth regulating Effect
From the above, it can be seen that: all compounds exert a growth promoting effect on plants, and generally have a significantly stronger growth promoting effect on dicot (radish) radicle and stem than on monocot (wheat), and generally have a substantially stronger growth promoting effect on radicle than stem. Wherein, the compounds with the highest growth promotion effect on dicotyledon (radish) radicle and stem are respectively compound No. 1, and the content of the compounds reaches 390 percent and 145 percent respectively at 20 ppm; the compound 6 with the highest growth promotion effect on monocot plant (wheat) radicle reaches 108% at 50ppm, while the compound 8 with the highest growth promotion effect on its stem reaches 199% at 50 ppm; but the most surprising is that the compound No. 8 has obvious growth promoting effect on radicle and stem of monocotyledonous and dicotyledonous plants (wheat and radish), and the highest promoting rate can reach about 200%. Therefore, such compounds, particularly, no. 1, no. 6, no. 8, no. 10, etc., can be developed as potent plant growth promoters.
Example 3
Effect of 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazolo [3,4-b ] [1,3,4] thiadiazines on HepG2 cell proliferation potency
Testing cell lines: hepG2 (human liver cancer cell line)
And (3) observing the indexes: inhibition of HepG2 cell proliferation by 10 Compounds
The evaluation method comprises the following steps: SRB method
The action time is as follows: 72hr
Test batch: 3 batches
The experimental water is distilled water produced by national medicine group; other reagents were purchased from national pharmaceutical group chemical reagent limited; the plate reader is made of Molecular Device company, model number: spectraMax 190.
The test method comprises the following steps:
the growth inhibition test of HepG2 cells adopts the SRB method. The method comprises the following specific steps: cells in the logarithmic growth phase are inoculated into 96-well culture plates according to proper density, 90 mu L of each well is cultured overnight, 10 compounds with different concentrations are added for 72 hours, three compound wells are arranged at each concentration, and solvent control and cell-free zeroing wells with corresponding concentrations are arranged. After the completion of the reaction, the adherent cells were decanted from the culture, 10% (w/v) trichloroacetic acid (100. Mu.L/well) was added and fixed at 4℃for 1 hour, followed by washing with distilled water five times, after drying at room temperature, SRB solution (Sigma, st.Louis, MO, U.S.A) (4 mg/mL in 1% glacial acetic acid) was added to each well, after incubation and staining at room temperature for 15 minutes, unbound SRB was washed off five times with 1% glacial acetic acid, after drying at room temperature, 10mM Tris solution 100. Mu.L was added to each well, and the optical density (OD value) at 560nm was measured by a SpectraMax 190 enzyme-labeled instrument.
The inhibition of cell proliferation by the compounds was calculated from the following formula:
inhibition (%) = (OD Control wells -OD Drug delivery hole )/OD Control wells ×100％。
Inhibition of HepG2 proliferation by the compounds of Table 4
TABLE 5 inhibition of HepG2 proliferation by doxorubicin
From the above, it can be seen that the antiproliferative effect of the compound on liver cancer cells HepG2 in vitro is very weak compared to the antiproliferative ability of doxorubicin. Since the antiproliferative effect of drugs on cells is generally broad spectrum, the compounds may be harmless and environment-friendly compounds, and certainly require more intensive research to prove.

Claims (1)

  1. The application of 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines is characterized in that the 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazines is used as a plant growth promoter, and the plant is monocotyledonous plant or dicotyledonous plant;
    the synthesis method of the 3-methyl-6-substituted-7-aroyl-6, 7-dihydro-5H- [1,2,4] triazole [3,4-b ] [1,3,4] thiadiazine compound comprises the following steps: adding absolute ethyl alcohol, triethylamine, equimolar 3-methyl-4-amino-5-mercapto-4H-1, 2, 4-triazole and substituted aromatic aldehyde into a flask, reacting under the reflux condition of 115-120 ℃, tracking by TLC, adding equimolar halogenated aryl ethyl ketone after the reaction is finished, finally removing solvent by rotary evaporation, and preparing a target product by using column chromatography;
    wherein, according to the substituted aromatic aldehyde R 1 CHO and haloaryl ethanone R 2 COCH 2 Substituent R of X 1 And R is 2 To obtain 10 target products, namely 2a,2b,2c,2d,2e,2f,2g,2h,2i,2j,
    the structural formula of the target product is as follows:
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107266474A (en) * 2017-07-28 2017-10-20 漳州卫生职业学院 To toluene triazole thiadiazine Benzophenone and synthetic method and application, single crystal cultivation

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CN107266474A (en) * 2017-07-28 2017-10-20 漳州卫生职业学院 To toluene triazole thiadiazine Benzophenone and synthetic method and application, single crystal cultivation

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DING Qi-Chun等.Synthesis, Crystal Structure and Biological Activities of Phenyl(6-phenyl-3-p-tolyl-6,7-dihydro-5H-[1,2,4]triazolo-[3,4-b] [1,3,4]thiadiazin-7-yl)methanone.《Chinese Journal of Structural Chemistry》.2020,第39卷(第8期),第1531-1538页，尤其是摘要，第1532-1533页. *
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