Preparation and application of cyanoacrylate compound with pyridine diarylamine structures

A technology of cyanoacrylate and pyridine diarylamine, which is applied in the field of pesticides, can solve problems such as environmental pollution, and achieve excellent control effects

Active Publication Date: 2016-07-06
NANTONG NTEC MONOFILAMENT TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the continuous expansion of the application scale of herbicides, the problem of drug resistance of traditional pesticide varieties has become increasingly prominent, and has brought serious environmental pollution, making the continued research and development of new pesticides an inevitable choice

Method used

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  • Preparation and application of cyanoacrylate compound with pyridine diarylamine structures
  • Preparation and application of cyanoacrylate compound with pyridine diarylamine structures
  • Preparation and application of cyanoacrylate compound with pyridine diarylamine structures

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] In a 50mL round bottom flask, add 5mmolIIa, 4mmolIII and 20mL absolute ethanol, heat to reflux for 8 hours, evaporate the solvent to dryness, add 30mL water to the residue, extract with 30mL ethyl acetate, combine the organic layers, wash with water, anhydrous Dried over magnesium sulfate, filtered with suction, evaporated the solvent under reduced pressure, separated and purified by column chromatography to obtain the target compound Ia with a yield of 61%; 1 HNMR (400MHz, d 6 -DMSO): δ10.20(s,1H,NH),9.67(s,1H,NH),8.49(s,1H,Py-H),7.87(dd,J 1 =2.4Hz,J 2 =2.0Hz,1H,Py-H),7.71(d,J=8.4Hz,2H,Ar-H),7.27(d,J=8.4Hz,2H,Ar-H),6.83-6.96(m,5H ,Ar-HandPy-H),4.75-4.76(m,2H,CH 2 ),4.40(t,J=4.4Hz,2H,CH 2 ), 4.14(t, J=4.4Hz, 2H, CH 2 ),3.69(s,3H,OCH 3 ),2.62(s,3H,SCH 3 ).

Embodiment 2

[0029]

[0030] In a 50mL round bottom flask, add 4mmolIIb, 4.4mmolIII and 20mL DMF, stir at room temperature for 6 hours, pour the reaction solution into 20mL ice water, extract with 30mL ethyl acetate, combine the organic layers, wash with water, dry over anhydrous magnesium sulfate, pump Filtration, evaporation of the solvent under reduced pressure, separation and purification by column chromatography gave the target compound Ib with a yield of 58%; 1 HNMR (400MHz, d 6 -DMSO): δ10.19(s,1H,NH),9.67(s,1H,NH),8.48(s,1H,Py-H),7.86(d,J=8.0Hz,1H,Py-H) ,7.70(d,J=8.0Hz,2H,Ar-H),7.44(d,J=8.0Hz,2H,Ar-H),7.27(d,J=12.0Hz,2H,Ar-H),6.93 -6.96(m,3H,Ar-HandPy-H),4.75(s,2H,CH 2 ),4.42(t,J=4.0Hz,2H,CH 2 ), 4.21(t, J=4.0Hz, 2H, CH 2 ),2.62(s,3H,SCH 3 ).

Embodiment 3

[0032]

[0033] In a 50mL round bottom flask, add 5mmolIIc, 6mmolIII and 25mL acetonitrile, heat to reflux for 6 hours, evaporate the solvent to dryness, add 20mL ice water to the reaction residue, extract with 30mL ethyl acetate, combine the organic layers, wash with water, Dry over magnesium sulfate, filter with suction, evaporate the solvent under reduced pressure, separate and purify by column chromatography to obtain the target compound Ic with a yield of 55%; 1 HNMR (400MHz, d 6 -DMSO): δ10.18(s,1H,NH),9.66(s,1H,NH),8.48(s,1H,Py-H),7.86(d,J=8.0Hz,1H,Py-H) ,7.70(d,J=8.0Hz,2H,Ar-H),7.30-7.37(m,1H,Ar-H),7.26(d,J=8.0Hz,2H,Ar-H),6.81-7.14( m,3H,Ar-HandPy-H),4.75(d,J=4.0Hz,2H,CH 2 ),4.42(t,J=4.0Hz,2H,CH 2 ), 4.22(t, J=4.0Hz, 2H, CH 2 ),2.62(s,3H,SCH 3 ).

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PUM

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Abstract

The invention relates to a cyanoacrylate compound (I) with pyridine diarylamine structures, a method for preparing the cyanoacrylate compound and application thereof.The method includes carrying out reaction on 3, 3-dimethyl sulfide-2-cyanoacrylate and diarylamine benzyl ammonia with pyridyl to obtain the cyanoacrylate compound.The cyanoacrylate compound with the pyridyl diarylamine structures, the method and the application have the advantages that excellent effects of preventing and controlling broadleaf weeds can be realized by the cyanoacrylate compound with the pyridyl diarylamine structures, and the cyanoacrylate compound can be used for preparing herbicides in the field of agriculture, horticulture and the like.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a cyanoacrylate compound containing a pyridine diarylamine structure and a preparation method and application thereof. Background technique [0002] The control of weeds has always been the core field of pesticide scientific research. The widespread use of herbicides has effectively controlled the weeds in crops. However, with the continuous expansion of the application scale of herbicides, the problem of drug resistance of traditional pesticide varieties has become increasingly prominent, and has brought serious environmental pollution, making the continued research and development of new pesticides an inevitable choice. [0003] Cyanoacrylate compounds were first seen in a French patent in 1969, but it was not until Huppatz first reported the Hill reaction inhibitory activity of such compounds in 1981 that they aroused great interest. Cyanoacrylate compounds are a class o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74A01N43/40A01P13/00
CPCA01N43/40C07D213/74
Inventor 戴红石玉军何海兵陈佳李阳葛书山叶林玉方源
Owner NANTONG NTEC MONOFILAMENT TECH CO LTD
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