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Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof

A technology of double quaternary ammonium salt and pyridine urea, applied in the field of pesticides, can solve the problems of high production cost, complex synthesis process, limited use and promotion, etc., and achieve the effect of solving poor water solubility, good water solubility, and promoting plant cell division

Active Publication Date: 2016-04-20
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After nearly half a century of rapid development, many phenylurea derivatives have become commercialized plant growth regulators with cytokinin activity, including diphenylurea, forchlorfenuron (1-(2-chloro- 4-pyridine)-3-phenylurea), thiadiuron (1-phenyl-3-(1,2,3-thiadiazole)-5-urea), etc., but due to their poor solubility in water, And some phenylurea derivatives have complex synthesis process and high production cost, which limits their use and promotion to a certain extent

Method used

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  • Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof
  • Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof
  • Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of 1,3-bis(N-octyl-3-pyridyl)urea bromide diquaternary ammonium salt

[0021] (1) Preparation of 1,3-di(3-pyridyl)urea: In a reaction flask, add 4.51g (48mmol) 3-aminopyridine, 3.53mL (48mmol) triethylamine and 80mL dichloromethane, start stirring , cooled to 0°C with an ice-water bath, dropwise added 2.85g (9.6mmol) of triphosgene in dichloromethane solution, controlled the rate of addition to keep the temperature of the reaction system below 5°C, the dropwise addition was completed in about half an hour, and then heated to reflux for reaction After 5 hours, cool, filter, wash with 10% aqueous sodium carbonate solution, wash with water, and dry to obtain 4.16 g of 1,3-bis(3-pyridyl)urea with a yield of 81%. 1 HNMR (300MHz, δppm, DMSO-d 6 ):8.97(s,2H),8.59(s,2H),8.18(d,2H),7.91(d,2H),7.30(t,2H).

[0022] (2) In the reaction flask, add 3.00g (14mmol) 1,3-bis(3-pyridyl)urea and 20mL (114.8mmol) n-octane bromide, heat to 120°C for 3 hours, cool, filter, Wash...

Embodiment 2

[0024] Preparation of 1,3-bis(N-decyl-3-pyridyl)urea bromide diquaternary ammonium salt

[0025] (1) The preparation of 1,3-bis(3-pyridyl)urea is the same as in Example 1;

[0026] (2) In the reaction flask, add 3.00g (14mmol) 1,3-bis(3-pyridyl)urea and 20mL (96.7mmol) brominated n-decane, heat to 110°C for 4 hours, cool, filter, Wash with acetone and dry to obtain 8.37 g of 1,3-di(N-n-decyl-3-pyridyl)urea diquaternary ammonium bromide, with a yield of 91.2% and a melting point of 252-253°C. 1 HNMR (300MHz, δppm, CDCl 3 ):10.99(s,2H),9.27(m,4H),8.45(m,2H),8.04(d,2H),4.80(t,4H),2.04(m,4H),1.44-1.21(m, 28H),0.83(m,6H).

Embodiment 3

[0028] Preparation of 1,3-bis(N-n-dodecyl-3-pyridyl)urea bromide diquaternary ammonium salt

[0029] (1) The preparation of 1,3-bis(3-pyridyl)urea is the same as in Example 1;

[0030] (2) In the reaction flask, add 3.00g (14mmol) 1,3-bis(3-pyridyl)urea and 20mL (83.5mmol) n-dodecane bromide, heat to 100°C for 5 hours, cool and filter , washed with acetone, and dried to obtain 9.00 g of 1,3-bis(N-n-dodecyl-3-pyridyl)urea diquaternary ammonium bromide, yield 90.3%, melting point: 254-255°C (dec) . 1 HNMR (300MHz, δppm, CDCl 3 ):11.04(s,2H),9.28(d,2H),9.21(s,2H),8.48(d,2H),8.09(m,2H),4.85(t,4H),2.08-1.24(m, 40H), 0.88(t,6H).

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Abstract

The invention relates to a pyridylurea biquaternary ammonium salt as well as a preparation method and application thereof. The preparation method of the pyridylurea biquaternary ammonium salt comprises the following steps: using 3-aminopyridine as a staring material, conducting reaction on 3-aminopyridine and triphosgene to obtain 1,3-bi(3-pyridyl)urea, and conducting reaction on 1,3-bi(3-pyridyl)urea and alkyl bromide under the solvent-free condition to prepare the pyridylurea biquaternary ammonium salt. According to the method, a solvent-free method is adopted to prepare the pyridylurea biquaternary ammonium salt, so that the environment can be protected, and the yield is relatively high. The provided pyridylurea biquaternary ammonium salt can be used as a plant growth regulator to promote plant cell division, and the problem that the traditional phenylurea plant growth regulator is poor in water solubility is solved.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a pyridineurea diquaternary ammonium salt and a preparation method thereof, and the application of the compound as a plant growth regulator in promoting plant cell division. Background technique [0002] Plant growth regulators are substances with similar physiological and biological effects to plant hormones, which can effectively regulate the growth and development of plants, including cell growth, division, rooting, germination, flowering, fruiting, maturation and shedding. A series of plant life processes are widely used in agriculture, forestry and horticultural crops, and play an increasingly important role. The composition of plant growth regulators is different, and their functions are also different. According to the different functions of plant growth regulators, we can roughly divide them into 3 categories: plant growth promoters, plant growth inhibitors and herbic...

Claims

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Application Information

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IPC IPC(8): C07D213/75A01N47/36A01P21/00A01P3/00A01P1/00
CPCA01N47/36C07D213/75
Inventor 郝俊生张永斌王攀于海英
Owner SHANXI UNIV
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