CN109896988A - A kind of synthesis of indole amides analog derivative and its application as plant growth regulator - Google Patents
A kind of synthesis of indole amides analog derivative and its application as plant growth regulator Download PDFInfo
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- CN109896988A CN109896988A CN201910211556.8A CN201910211556A CN109896988A CN 109896988 A CN109896988 A CN 109896988A CN 201910211556 A CN201910211556 A CN 201910211556A CN 109896988 A CN109896988 A CN 109896988A
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- indoles
- indole amides
- analog derivative
- indole
- acyl chlorides
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- -1 indole amides Chemical class 0.000 title claims abstract description 59
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 41
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 39
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 title claims description 14
- 238000003786 synthesis reaction Methods 0.000 title claims description 14
- 150000002475 indoles Chemical class 0.000 claims abstract description 15
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010189 synthetic method Methods 0.000 claims abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 230000001376 precipitating effect Effects 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-ethyl-N-phenylamine Natural products CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 241000209140 Triticum Species 0.000 abstract description 12
- 235000021307 Triticum Nutrition 0.000 abstract description 12
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 7
- 230000012010 growth Effects 0.000 abstract description 5
- 150000001408 amides Chemical class 0.000 abstract description 4
- 238000012271 agricultural production Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 4
- 239000012086 standard solution Substances 0.000 description 4
- IGOKKRACOOYNCR-UHFFFAOYSA-N 4-[2-(4-cyanophenoxy)ethoxy]benzonitrile Chemical compound C1=CC(C#N)=CC=C1OCCOC1=CC=C(C#N)C=C1 IGOKKRACOOYNCR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 244000230712 Narcissus tazetta Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
Abstract
It the invention discloses a kind of indole amides analog derivative and its synthetic method, has been synthesized by Conventional solvents method and ultrasonic irradiation a kind of using indyl as the amide derivatives of skeleton using indoles, oxalyl chloride, arylamine as primary raw material.Due to both containing indolyl radical in indole amides molecule, there is amide structure again, it is shown under the conditions of optium concentration to the apparent facilitation of wheat growth, has more promotion advantage than heteroauxin, therefore be applied to that there is good prospect in agricultural production as plant growth regulator.
Description
The present invention relates to a kind of synthetic method of indole amides compound, the present invention also relates to indole amides compound
In the regulation performance of plant growth kind, belong to compound synthesis field and.
Background technique
Indoles, also known as benzopyrrole, indoles are widely present in nature, are primarily present in natural flower oil, such as jasmine
Flower, daffodil, fragrant rowland etc..Indoles has good bioactivity, obtains in fields such as pesticide, medicine, antifouling, dyestuff and fragrance
To be widely applied.Indole derivatives are very wide in distributed in nature, all contain indole ring in the structure of many native compounds, some
The derivative of indoles is closely related with vital movement, can be widely used for efficient plant growth regulator, fungicide etc., such as indoles second
Acid, indole -3-butyric acid are a kind of important plant modifying agents.However, at present for indole amides class as plant growth regulating
The report of agent is not too much common.
Summary of the invention
The object of the present invention is to provide a kind of using indyl as the synthetic method of the indole amides derivative of skeleton, to make
It is applied in agricultural production for plant growth regulator.
One, indole amides analog derivative
For the present invention using indyl as the indole amides derivative of skeleton, structure is as follows:
The synthetic method of indole amides analog derivative, comprising the following steps:
(1) indoles the synthesis of indoles acyl chlorides: is dissolved in anhydrous ether；It is slowly added into after oxalyl chloride is diluted with anhydrous ether
In indoles solution, it is stirred to react generation bright yellow precipitate under stirring strongly under ice-water bath conditional, filters, is washed with anhydrous ether
It washs, obtains glassy yellow crystal indoles acyl chlorides；Wherein the molar ratio of indoles and oxalyl chloride is 1:1 ~ 1:1.5；Be stirred to react the time be 60 ~
70min。
(2) synthesis of indole amides: indoles acyl chlorides is dissolved in ethyl acetate, and aniline and phase transfer catalyst is added
PEG-400, is stirred to react 10 ~ 12 minutes at room temperature or Ultrasonic Radiation reacts 8 ~ 10 minutes under 23 ~ 27 DEG C of constant temperature；It adds
NaOH aqueous solution the reaction was continued generation in 0.7 ~ 1 hour precipitating, filters, inorganic salts is first washed with water, then washed with ethyl acetate solution
Precipitating is washed, dry, crude product DMF-H2O mixed solvent recrystallization, obtains indole amides, is labeled as A1.
The molar ratio of indoles acyl chlorides and aniline is 1:0.8 ~ 1:1.25.
The molar ratio of indoles acyl chlorides and phase transfer catalyst is 1:0.3 ~ 1:0.5.
NaOH effect is to neutralize the hydrochloric acid that indoles acyl chlorides and aniline reaction generate, and promotes the reaction to carry out completely, indoles acyl
The molar ratio of chlorine and NaOH are 1:0.1 ~ 1:0.3.
The mixing speed being stirred to react is 250 ~ 300 revs/min.
The synthesis formula of indole amides A1 is as follows:
The product of above-mentioned synthesis shows that the product of synthesis is indole amides through FT-IR and elemental analysis.Anal. Found: C,
71.10%; H, 4.69%; N, 10.42%。Calcd. for C16H12N2O2 (264.28): C, 72.71%; H,
4.59%; N, 10.60%。
Two, the plant growth regulating performance of indole amides analog derivative
Measuring method:
(1) wheat seed is taken to be rinsed with water for several times, drain well is coated with moist towel, and coating makes its sprouting in 12 hours；
(2) the indole amides A1 of 0.2643g is weighed in 10 mL test tubes, and 2 drops emulsifier (Tween-80,0.08g) are added, with
DMSO dilution is settled to 10 mL, is configured to the A1 concentrated solution of 26.43g/L, for use；
(3) 38 are added into 5 10mL test tubes respectivelyμL、3.8μL、0.38μL、0.038μL、0.0038μThe above-mentioned A1 concentrated solution of L,
It is settled to 10mL with distilled water dilution, being made into concentration is respectively 100mg/L, 10 mg/L, 1 mg/L, 0.1 mg/L, 0.01 mg/
The series standard solution of L；
(4) weigh a certain amount of heteroauxin, according to the method described above compound concentration be respectively 100 mg/L, 10 mg/L, 1 mg/L,
The series standard solution of 0.1 mg/L, 0.01 mg/L；
(5) secondary distilled water, above-mentioned various concentration A1 series standard solution and heteroauxin series standard solution are respectively taken 8 ~
10mL in the culture dish that diameter is 10cm, respectively plus open, and so that liquid level is just submerged filter paper, puts on filter paper by circular filter paper piece two
6 ~ 8 pieces of the wheat seed sprouted, then covers lid, allows its sprouting to show money or valuables one carries unintentionally, removes lid after showing money or valuables one carries unintentionally by it and grow five naturally
By seven days, every morning supplemented corresponding solution；
(6) length of wheat seed root and bud in each culture dish is measured with ruler, blank is done with distilled water result, with heteroauxin
As a result it compares, according to the following formula inhibitory effect or facilitation effect of the indole amides A1 to wheat growth under calculating various concentration:
Wherein, positive value indicates that facilitation effect, negative value indicate inhibitory effect.Blank group is distilled water.
Test effect: calculated value is as shown in Table 1 and Table 2:
As seen from the results in Table 1, indole amides A1 when concentration is 0.01 mg/L to the growth-promoting effect of wheat seed root most
It is good, and concentration more Seedling height inhibiting effect is more serious, it is maximum to the growth inhibition effect of wheat seed root in 100 mg/L.With
Same concentrations heteroauxin compares, and when promoting optium concentration, indole amides A1 shows the growth of wheat seed root stronger
Facilitation.
As seen from the results in Table 2, indole amides A1 when concentration is 1 mg/L to the growth-promoting effect of wheat seed bud most
It is good, and concentration is maximum to the growth inhibition effect of wheat seed bud in 0.1 mg/L.Compared with same concentrations heteroauxin,
When promoting optium concentration, indole amides A1 still shows stronger facilitation to the growth of wheat seed bud.
In conclusion the present invention using indoles, oxalyl chloride, arylamine as primary raw material, passes through Conventional solvents method and ultrasonic amplitude
The method of penetrating has synthesized a kind of using indyl as the amide derivatives of skeleton.Due to both containing indolyl radical in indole amides molecule,
There is amide structure again, shown under the conditions of optium concentration to the apparent facilitation of wheat growth, had more than heteroauxin
Promotion advantage, therefore it is applied to that there is good prospect in agricultural production as plant growth regulator.
Specific embodiment
The synthesis of indole amides A1 of the present invention and performance are described further below by specific embodiment.
Embodiment 1
(1) 1.172 g(0.01 mol the synthesis of indoles acyl chlorides: are weighed) indoles, be added 40 mL anhydrous ethers indoles is dissolved
In 250mL round-bottomed flask, weighs equimolar amounts oxalyl chloride and diluted with a small amount of anhydrous ether, then stirred strongly in ice-water bath
It mixes down and is slowly added in flask, be stirred to react 1 hour, there is bright yellow precipitate generation, filter, washed three times, obtained with anhydrous ether
It is spare to glassy yellow crystal indoles acyl chlorides.Yield: 90%；
(2) synthesis of indole amides: 2.075 g indoles acyl chlorides (0.01mol) are weighed, are dissolved in 250mL with 40mL ethyl acetate
In round-bottomed flask, the aniline and 12 drop (about 0.6mL) phase transfer catalyst PEG-400 of 1.25 times of moles is added, 300 under room temperature
Rev/min mixing speed under react 10 minutes, the NaOH aqueous solution that 10mL concentration is 5% is added, is further continued for reaction 1 hour, has big
Amount precipitating generates, and filters, inorganic salts is washed with water, then wash precipitating with ethyl acetate solution, dry.Crude product DMF-H2O
Mixed solvent is recrystallized to give target compound indole amides A1, yield 61.4%.
A1 (C16H12N2O2): for light yellow crystal, fusing point: 247.2 ~ 248.1 DEG C. Anal. Found: C, 71.10;
H, 4.69; N, 10.42. Calcd. for C16H12N2O2 (264.28): C, 72.71; H, 4.59; N, 10.60.
FT-IR (KBr, cm-1): 3300.62,3227.45,1680.89,1627.96,1619.95,1527.33,1501.48,
1486.26,1425.52,1312.21,1240.75,1138.08,1129.79,893.28,754.94,742.78,664.45,
651.73,609.44.
Embodiment 2
(1) synthesis of indoles acyl chlorides: with embodiment 1；
(2) synthesis of indole amides: 2.075 g indoles acyl chlorides (0.01mol) are weighed, are dissolved in 250mL with 40mL ethyl acetate
In round-bottomed flask, the aniline and 12 drop (about 0.6mL) phase transfer catalyst PEG-400 of 1.25 times of moles, 25 DEG C of constant temperature are added
Lower Ultrasonic Radiation reacts 8 minutes, and the NaOH aqueous solution that 10mL concentration is 5% is added, is further continued for reaction 41 minutes, and there have to be a large amount of heavy
It forms sediment and generates, filter, inorganic salts are washed with water, then wash precipitating with ethyl acetate, it is dry.Crude product DMF-H2O mixed solvent
It is recrystallized to give target compound indole amides A1.Yield obtained by ultrasonic irradiation is 71.7%.The characterize data of A1 is the same as implementation
Example 1.
Through comparing embodiment 1,2, the reaction time needed for ultrasonic irradiation is shorter, and products collection efficiency is higher, compares Conventional solvents
Method has more advantage.
Claims (9)
1. a kind of indole amides analog derivative, structure are as follows:
。
2. the synthetic method of indole amides analog derivative as described in claim 1, comprising the following steps:
(1) indoles the synthesis of indoles acyl chlorides: is dissolved in anhydrous ether；It is slowly added into after oxalyl chloride is diluted with anhydrous ether
In indoles solution, it is stirred to react generation bright yellow precipitate under stirring strongly under ice-water bath conditional, filters, is washed with anhydrous ether
It washs, obtains glassy yellow crystal indoles acyl chlorides；
(2) synthesis of indole amides: indoles acyl chlorides is dissolved in ethyl acetate, and aniline and phase transfer catalyst PEG- is added
400, it is stirred to react at room temperature 10 ~ 12 minutes or Ultrasonic Radiation reacts 8 ~ 10 minutes under 23 ~ 27 DEG C of constant temperature；Add NaOH
Aqueous solution the reaction was continued generation in 0.7 ~ 1.0 hour precipitating, filters, inorganic salts is first washed with water, then washed with ethyl acetate solution
Precipitating, dry, crude product DMF-H2O mixed solvent recrystallization, obtains indole amides.
3. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (1), indoles and grass
The molar ratio of acyl chlorides is 1:1 ~ 1:1.5.
4. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (1), be stirred to react
Time is 60 ~ 70min.
5. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (2), indoles acyl chlorides
Molar ratio with aniline is 1:0.8 ~ 1:1.25.
6. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (2), indoles acyl chlorides
Molar ratio with phase transfer catalyst is 1:0.3 ~ 1:0.5.
7. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (2), indoles acyl chlorides
Molar ratio with NaOH is 1:0.1 ~ 1:0.3.
8. the synthetic method of indole amides analog derivative as described in claim 1, it is characterised in that: in step (2), be stirred to react
Mixing speed be 250 ~ 300 revs/min.
9. application of the indole amides analog derivative as described in claim 1 as plant growth regulator.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112973714A (en) * | 2021-03-24 | 2021-06-18 | 甘肃农业大学 | Catalyst for preparing cyclopentene, preparation method and application thereof |
| CN114403150A (en) * | 2022-02-09 | 2022-04-29 | 中国农业大学 | Application of indoleamide compound as trehalose-6-phosphate synthase inhibitor |
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Cited By (3)
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| CN112973714A (en) * | 2021-03-24 | 2021-06-18 | 甘肃农业大学 | Catalyst for preparing cyclopentene, preparation method and application thereof |
| CN114403150A (en) * | 2022-02-09 | 2022-04-29 | 中国农业大学 | Application of indoleamide compound as trehalose-6-phosphate synthase inhibitor |
| CN114403150B (en) * | 2022-02-09 | 2022-11-04 | 中国农业大学 | Application of indoleamide compound as trehalose-6-phosphate synthase inhibitor |
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Application publication date: 20190618 |