N-(1, 2-diphenyl-2-amino)-thiophosphoramide salt and application thereof

A thiophosphoramide and diphenyl technology, which is applied to N--thiophosphoramide salts and their application fields as pesticides, can solve the problems of being easily oxidized and limited use, and achieve enhanced stability and good chemical stability. Effect

Active Publication Date: 2015-12-09
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because N-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosphoramide contains primary amine functional groups, it is easily oxidized when placed in the air, thus limiting the use of such compounds in Other uses

Method used

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  • N-(1, 2-diphenyl-2-amino)-thiophosphoramide salt and application thereof
  • N-(1, 2-diphenyl-2-amino)-thiophosphoramide salt and application thereof
  • N-(1, 2-diphenyl-2-amino)-thiophosphoramide salt and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1. The chemical structural formulas and physical constants of some N-(1,2-diphenyl-2-amino)-thiophosphoramide salts are shown in Table 1:

[0020] Table 1. Some chemical structural formulas and physical constants of N-(1,2-diphenyl-2-amino)-thiophosphoramide salts

[0021]

[0022]

[0023]

[0024] Compared with the known parent compound N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylphosphorothioate, the above-mentioned preferred compound has outstanding advantages, which are specifically shown in : (1) The stability of light and heat is significantly enhanced. Under the same conditions, it is irradiated with a fluorescent lamp or controlled at 80°C for 24 hours and then qualitatively detected by NMR. The above compounds do not change, while the control sample N-(1R,2R)-( 1,2-Diphenyl-2-amino)-P,P-diphenylphosphorothioate has been mostly decomposed. (2) Enhanced water solubility, the control sample N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosp...

Embodiment 2

[0025] Example 2: Preparation of target compound N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosphoramide hydrochloride (1)

[0026] At 0°C, (1R,2R)-diphenylethylenediamine (2.12g, 0.01mmol) was dissolved in dichloromethane (10mL), triethylamine (1.4mL) was added, stirred in the reactor, Then diphenylphosphorylthiochloride (0.252g, 0.01mmol) was dissolved in dichloromethane (30mL), added dropwise to the reaction system with a constant pressure dropping funnel, and then detected by TLC. After phosphorus oxychloride disappears, vacuum precipitation, column chromatography purification, the obtained product N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosphoramide . White solid with a yield of 81% and a melting point of 118-120°C. [α] 2 D 0 –23.4 (c1.0, CHCl 3 ); 1 HNMR (CDCl 3 ,400MHz):1.80(s,2H),4.19(t,J=6.8Hz,1H),4.25(d,J=5.6Hz,1H),4.44-4.51(m,1H),7.05-7.08(m, 2H),7.11-7.15(m,3H),7.18-7.22(m,2H),7.24-7.38(m,9H),7.58-7.65(m,4H);31 PNMR (CDCl 3 ,161.7MHz):59....

Embodiment 3

[0028] Example 3: Preparation of target compound N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosphoramide hydrobromide (2)

[0029] Dissolve N-(1R,2R)-(1,2-diphenyl-2-amino)-P,P-diphenylthiophosphoramide (1mmol) in chloroform (10mL) and methanol (10mL) Hydrogen bromide solution (48%, 1 mL) was added dropwise to the mixed solution, and reacted at room temperature for 3 hours, then anhydrous sodium sulfate was added to dry it, and the corresponding salt was obtained by vacuum precipitation. White solid with a yield of 79% and a melting point of 174-177°C. 1 HNMR (CDCl 3 ,400MHz):4.70-4.79(m,1H),4.89(s,1H),5.76(t,J=10.8Hz,1H),6.95-6.97(m,2H),7.07-7.23(m,10H), 7.33-7.37(m,1H),7.44-7.50(m,3H),7.57-7.62(m,2H),7.89-7.94(m,2H),8.70(s,3H); 31 PNMR (CDCl 3 ,161.7MHz):64.16; 13 CNMR (CDCl 3 ,100.6MHz):59.7(d,J=2.8Hz),60.0,127.8,127.9,128.0,128.1,128.2,128.4,128.6,128.7,128.9,129.3,131.3,131.4,131.6,131.75,131.018,132. , 132.28, 132.31, 132.33, 132.6, 133.1, 134.2, 138.4 (d, ...

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Abstract

The invention relates to an N-(1, 2-diphenyl-2-amino)-thiophosphoramide salt compound and application thereof. The structural formula of the compound is shown as the specification (with the definitions of the groups being shown in the specification). The compound provided by the invention is applied to inhibition of tobacco mosaic virus, pepper virus, tomato virus, sweet potato virus, potato virus, cucurbit virus and maize dwarf mosaic virus, can effectively control the virus diseases of tobacco, hot pepper, tomatoes, cucurbites, grains, vegetables, beans and other crops, and is especially suitable for control of tobacco mosaic virus. (structural formula).

Description

technical field [0001] The present invention relates to N-(1,2-diphenyl-2-amino)-thiophosphoramide salt and its application as pesticide. Background technique [0002] Plant viruses are widely distributed in nature. They cause serious damage to the growth of crops, and then cause great losses to modern agricultural production. Tobacco mosaic virus (TMV), as a pathogen, can cause harm to many crops. According to statistics, it can infect about 198 kinds of individuals of 22 kinds of monocots, and can cause about 5% to 90% loss (Hari, V.; Das, P. Ultramicroscopic detection of plant viruses and their gene products. Inplant disease virus control. Hadidi, A.; Khetarpal , R.K.; Koganezawa, H., Eds.; APSPress: St. Paul, MN, 1998:417-427.). So far, no chemical pesticide has been able to completely protect crops from TMV. Likewise, there is no single drug that can completely cure TMV-infested crops. Although there are many types of anti-plant virus agents, such as benzothiadiazole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/36A01N57/28A01P1/00
Inventor 卢爱党张娅迪李玉山马园园陈建新
Owner HEBEI UNIV OF TECH
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