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Synthetic method and agricultural biological activity of benzothiadiazine compound

A technology of benzothiadiazine and synthesis method, which is applied in the fields of chemicals for biological control, biocides, organic chemistry, etc., and can solve the problem of expensive consumption of benzothiadiazine compound solutions and metal rhodium catalysts , poor selectivity and other problems, to achieve the effect of cheap and easy to obtain dosage, less catalyst dosage and simple reaction system

Inactive Publication Date: 2019-06-21
QINGDAO AGRI UNIV
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  • Application Information

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Problems solved by technology

However, in the above-mentioned preparation process, the metal rhodium catalyst used is expensive and used in a large amount, and silver nitrate and carboxylate are used as additives, the experimental cost is high, the selectivity is not good and the yield is medium
Therefore, the method currently provided is not economical, nor is it the optimal solution in the experimental synthesis of benzothiadiazines

Method used

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  • Synthetic method and agricultural biological activity of benzothiadiazine compound
  • Synthetic method and agricultural biological activity of benzothiadiazine compound
  • Synthetic method and agricultural biological activity of benzothiadiazine compound

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preparation example Construction

[0021] The embodiment of the present invention provides a synthesis method of benzothiadiazine compounds, comprising the following steps:

[0022] S1: Add sulfinimide compounds and nitrobenzene compounds to the reactor respectively, under the action of nickel diacetylacetonate or nickel chloride and solvent, seal and react at 80-110°C for 5-8 hours in air .

[0023] In this step, benzothiadiazine compounds are synthesized by using sulfinimide compounds and nitrobenzene compounds. Specifically, under the action of catalyst nickel, sulfenimide compounds react with nickel to form five The membered ring compound is then further reacted with nitrobenzene compounds to introduce amino groups, and finally continues to react with another molecule of nitrobenzene compounds to generate the target product. What needs to be explained here is that this step reaction does not need to be heated, and the reaction can be carried out under air conditions. The catalyst dosage of nickel diacetyla...

Embodiment 1

[0040] Add 1mmol to the reactor 2.3mmol 0.02mmol of nickel diacetylacetonate and 3ml of 1,1-dichloroethane were sealed and reacted at 100°C in air for 5 hours; after the reaction, column chromatography was performed to obtain the following C1 compound:

[0041]

[0042] Carry out nuclear magnetic spectrum analysis to above-mentioned light yellow solid powder, data is as follows:

[0043] 1 H NMR (500MHz, CDCl 3 )δ=8.29(d, J=8.4Hz, 2H), 8.17(d, J=8.4Hz, 2H), 7.95(d, J=7.6Hz, 2H), 7.67-7.62(m, 5H), 7.53( t,J=7.6Hz,2H),7.37-7.31(m,2H),6.83(d,J=8.5Hz,1H),6.72(t,J=7.6Hz,1H),6.21(s,1H), 5.16(d, J=17.6Hz, 1H), 4.61(d, J=17.1Hz, 1H);

[0044] 13 C NMR (125MHz, CDCl 3)δ=148.8, 147.7, 147.4, 144.3, 144.3, 140.2, 134.8, 133.4, 129.2, 128.6, 128.4, 127.8, 127.6, 124.4, 124.0, 121.6, 118.3, 114.7, 75.9, 53.8;

[0045] After identification, the spectral data corresponded to the structural formula, proving that the synthesized product was (1S,3R)-4-(4-nitrobenzyl)-3-(4-nitrophen...

Embodiment 2

[0047] Add 1mmol to the reactor 2.3mmol 0.02mmol of nickel chloride and 3ml of 1,1-dichloroethane were sealed and reacted at 110°C for 8 hours in the air; after the reaction, column chromatography was performed to obtain the following C2 compound:

[0048]

[0049] Carry out nuclear magnetic spectrum analysis to above-mentioned light yellow solid powder, data is as follows:

[0050] 1 H NMR (500MHz, CDCl 3 )δ=8.26(d, J=8.4Hz, 2H), 8.17(d, J=8.8Hz, 2H), 7.83(d, J=8.0Hz, 2H), 7.66(d, J=8.4Hz, 2H) ,7.61(d,J=8.4Hz,2H),7.32(t,J=8.0Hz,2H),7.21(d,J=8.0Hz,1H),6.63(s,1H),6.54(d,J= 8.0Hz, 1H), 6.21(s, 1H), 5.11(d, J=17.2Hz, 1H), 4.58(d, J=17.6Hz, 1H), 2.43(s, 3H), 2.25(s, 3H) ;

[0051] 13 C NMR (125MHz, CDCl 3 )δ=149.1, 147.7, 147.5, 145.9, 144.6, 144.4, 144.2, 137.6, 130.1, 128.6, 128.3, 127.8, 127.6, 124.4, 123.9, 119.6, 119.4, 114.8, 75.8, 53.8, 21.4, 262.4;

[0052] After identification, the spectral data corresponded to the structural formula, proving that (1S,3R)-6-...

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Abstract

The invention provides a synthetic method and agricultural biological activity of a benzothiadiazine compound and belongs to the field of organic synthesis. The synthetic method is simple in reactionsystem, a used catalyst is cheap, easy to obtain and less in dosage, other metals and carboxylates are not needed as additives, the yield is high, and the benzothiadiazines compound can be efficientlysynthesized. The invention adopts the technical scheme that the synthetic method comprises the following steps: respectively adding a sulfonimide compound and a nitrobenzene compound into a reactor and sealing under the air condition of 80-110 DEG C under the action of nickel diacetylacetone or nickel chloride and a solvent to react for 5-8 hours; after the end of reaction, performing column chromatography separation to obtain the benzothiadiazine compound. The benzothiadiazine compound can be applied to physalospora piricola.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of benzothiadiazine compounds and their agricultural biological activity. Background technique [0002] Benzothiadiazines have a variety of biological activities, and have achieved satisfactory multi-faceted effects in recent years, and have attracted more and more attention from chemical researchers all over the world. At present, the existing available preparation method of benzothiadiazine compounds is to utilize sulfenimide compounds and nitrobenzene compounds in an expensive metal rhodium catalyst, and have silver nitrate and carboxylate as additives It was prepared by reacting at high temperature for 24 hours under certain conditions (Org. Chem. Front., 2019, DOI: 10.1039 / C9QO00112C). However, in the above-mentioned preparation process, the metal rhodium catalyst used is expensive and used in a large amount, and silver nitrate and carboxylate...

Claims

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Application Information

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IPC IPC(8): C07D285/24A01P3/00
Inventor 王祖利董道青王艳丽杨洪迪丁彩真陈德茂韩晴晴吴琼李光辉
Owner QINGDAO AGRI UNIV
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