5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds, preparation method and application thereof

A kind of technology of amino imidazolidinone and butenolide, applied in the field of agricultural chemistry

Inactive Publication Date: 2015-02-25
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, there is no specific application of combining the butenolactone structure with imidazolinone compounds

Method used

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  • 5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds, preparation method and application thereof
  • 5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds, preparation method and application thereof
  • 5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the synthesis of compound TB-1

[0058]The structural formula of compound TB-1 is as follows:

[0059]

[0060] Among them, n=1, R 1 = H, R 2 =CH 3 , R 3 =H.

[0061] Concrete preparation steps are as follows:

[0062] 1) Synthesis of Compound Ia (n=1, R 1 = H, R 2 =CH 3 ):

[0063] Take 7.1g (50mmol) of 1-hydroxycyclohexyl methyl ketone and 1mL of triethylamine into a 100mL three-necked flask, heat the oil bath to 60°C, add 8.4g (100mmol) of diketene dropwise, and heat to After 12 hours of reaction at 70°C, the reaction was stopped, and the excess liquid was distilled off under reduced pressure. The residue was separated by column chromatography (200-300 mesh silica gel, petroleum ether / ethyl acetate as eluent, 5:1 gradient elution), Obtained 13.34g colorless crystal Ia, yield 51%;

[0064] After testing, Compound Ia: m.p.98~99℃.

[0065] 1 H NMR (300MHz, CDCl 3 )δ:2.57(s,3H),2.33(s,3H),1.86-1.67(m,7H),1.53-1.50(m,2H),1.30-1.23(m,1H). ...

Embodiment 2

[0078] The synthesis of embodiment 2 compound TB-10

[0079] The structural formula of compound TB-10 is as follows:

[0080]

[0081] Among them, n=1, R 1 = H, R 2 =C 6 h 5 , R 3 =H.

[0082] Compound TB-10 was prepared according to the method of Example 1, the difference being: the 1-hydroxycyclohexyl methyl ketone in step 1) was replaced by 1-hydroxycyclohexyl phenyl ketone to obtain compound Ib; correspondingly obtain IIb, IIIb, TB-10.

[0083] After testing, compound Ib was a colorless crystal with a yield of 99%, m.p.137-138°C. 1 H NMR (300MHz, CDCl 3 )δ:7.50-7.45(m,3H),7.20-7.16(m,2H),2.38(s,3H),1.84-1.61(m,9H),1.14-1.13(m,1H).

[0084] Compound IIb: white solid, yield 60%, m.p.284~286℃. 1 H NMR (300MHz, CDCl 3 )δ:12.20(s,1H),11.95(s,1H),7.50-7.43(m,3H),7.25-7.20(m,2H),1.82-1.46(m,12H),1.15-1.06(m, 1H); HR-ESI-MS m / z: C 20 h 21 N 2 o 3 S[M+H] + ,Cacld.369.1267,found369.1258.

[0085] Compound IIIb: yellow crystal, yield 90%, m.p.252~254℃. 1 H NMR (...

Embodiment 3

[0087] The synthesis of embodiment 3 compound TB-19

[0088] The structural formula of compound TB-19 is as follows:

[0089]

[0090] Among them, n=1, R 1 =CH 3 , R 2 =CH 3 , R 3 =H.

[0091] Compound TB-19 was prepared according to the method of Example 1, the difference being that 1-hydroxycyclohexyl methyl ketone was replaced by 1-hydroxyl-4-methylcyclohexyl methyl ketone in step 1) to obtain compound Ic; correspondingly IIc, IIIc, TB-19 were obtained.

[0092] After detection, compound Ic: colorless crystal, yield 61%, m.p.36~37℃. 1 H NMR (300MHz, CDCl 3 )δ:2.56(s,3H),2.41(s,1.5H),2.36(s,1.5H),2.12-1.33(m,9H),1.06(d,J=7.1Hz,1.5H),0.98( d,J=7.1Hz,1.5H).

[0093] Compound IIc: white solid, yield 54%, m.p.273~276℃. 1 H NMR (300MHz, CDCl 3 )δ:12.20-12.12(m,1H),11.96-11.71(m,1H),2.22-1.23(m,15H),1.05-0.92(m,3H); HR-ESI-MS m / z:C 16 h 21 N 2 o3 S[M+H] + ,Cacld.321.1267,found321.1259.

[0094] Compound IIIc: yellow crystal, yield 86%, m.p.151~152℃. 1 H NMR (3...

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Abstract

The invention relates to 5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds, a preparation method and application thereof. The imidazolinone compounds have a structure with general formula of TB. The 5-(butane lactone-3-ethylidene)-2-amino imidazolinone compounds with the general structure of TB have good bactericidal effect on various types of phytopathogen such as rice sheath blight disease, sclerotinia rot of colza and phytoph-thora capsici leonian germs.

Description

technical field [0001] The invention relates to a 5-(butenolactone-3-ethylene)-2-aminoimidazolinone compound, a preparation method and an application as an agricultural fungicide, belonging to the field of agricultural chemistry. Background technique [0002] Imidazolinone compounds are widely used as herbicides, and their commercial products include six kinds of imazaquin, imazapyr, imazethapyr, imazethapyr, imazethapyr, and imazethapyr. Obvious, but the bactericidal effect is general, especially for plant pathogenic bacteria, EC 50 larger. [0003] The butenolide structure widely exists in various natural products and has important applications in the field of medicinal chemistry research. In the field of pesticides, commercialized pesticides with butenolactone structural fragments include insecticides and acaricides, spirodiclofen, spiromethin, and spirotetramat. In recent years, different research groups at home and abroad have synthesized some new ones. The compounds...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06A01P3/00
CPCC07D405/06
Inventor 王明安汤博杜鹃杨明艳
Owner CHINA AGRI UNIV
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