Urea carbamate methyl substituted arly ester with bactericidal activity

A technology of ureamethyl carbamate and bactericidal activity, which is applied in the field of pesticides to achieve the effects of easy-to-obtain raw materials, simple synthesis, and broadened biological activity spectrum

Inactive Publication Date: 2011-04-20
HUNAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the excessive use of carbamate insecticides in re

Method used

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  • Urea carbamate methyl substituted arly ester with bactericidal activity

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example 1

[0050] Example 1: Synthesis of 4-(N-methyl-N'-phenylureidomethyl)phenyl N-methylcarbamate.

[0051] 4-(anilinomethyl)phenol (1.99g, 0.01mol), Et 3 N (5.06mg, 0.05mmol) was dissolved in chloroform, stirred continuously at room temperature (about 30°C), slowly added methyl isocyanate (CH 3 NCO, 2.85g, 0.05mol), after adding dropwise for 10 minutes, continue to react at 60~65°C for 1 hour, stop the reaction, desolvate under reduced pressure to obtain a yellow oily substance, separate and purify by flash column chromatography to obtain a white solid Product, yield: 66.8%, melting point (mp): 151.2-153.1°C.

[0052] 1 H NMR (CDCl 3 , 500MHz) δ : 7.33~7.36(m, 2H), 7.27~7.29(m, 1H), 7.21~7.23(m, 2H), 7.07~7.09(m, 2H), 7.00~7.02(m, 2H), 4.84(s, 2H, CH 2 ), 2.95(s, 3H, CH 3 ), 2.75(s, 3H, CH 3 ). 13 C NMR (CDCl 3, 125MHz) δ : 157.73, 155.21, 150.05, 141.46, 135.59, 129.87(2C), 129.22(2C), 128.61(2C), 127.69(2C), 121.29, 52.48, 27.59, 27.44. IR (KBr) n: 3383, 3310, 3289, 29...

example 2

[0053] Example 2: Synthesis of 4-(N-methyl-N'-(4-methylphenyl)ureidomethyl)phenyl N-methylcarbamate.

[0054] 4-((4-methylanilino)methyl)phenol (2.13g, 0.01mol), Et 3 N (5.06mg, 0.05mmol) was dissolved in chloroform, stirred continuously at room temperature (about 30°C), slowly added methyl isocyanate (CH 3 NCO, 2.85g, 0.05mol), after adding dropwise for 10 minutes, continue to react at 60~65°C for 1 hour, stop the reaction, desolvate under reduced pressure to obtain a yellow oily substance, separate and purify by flash column chromatography to obtain a white solid Product, yield: 66.9%, melting point (mp): 143.1-144.7°C.

[0055] 1 H NMR (CDCl 3 , 500MHz) δ : 7.20~7.22(m, 2H), 7.11~7.13(m, 2H), 6.99~7.00(m, 2H), 6.92~6.94(m, 2H), 4.80(s, 2H, CH 2 ), 2.94(s, 3H, CH 3 ), 2.73(s, 3H, CH 3 ), 2.32(s, 3H, CH 3 ). 13 C NMR (CDCl 3, 125MHz) δ : 157.93, 155.26, 150.03, 138.65, 137.68, 135.67, 130.47(2C), 129.24(2C), 128.41(2C), 121.26(2C), 52.45, 27.57, 27.41, 20.96. IR ...

example 3

[0056] Example 3: Synthesis of 4-(N-methyl-N'-(4-methoxyphenyl)ureidomethyl)phenyl N-methylcarbamate.

[0057] 4-((4-Methoxyanilino)methyl)phenol (2.28g, 0.01mol), Et 3 N (5.06mg, 0.05mmol) was dissolved in chloroform, stirred continuously at room temperature (about 30°C), slowly added methyl isocyanate (CH 3 NCO, 2.85g, 0.05mol), after adding dropwise for 10 minutes, continue to react at 60~65°C for 1 hour, stop the reaction, desolvate under reduced pressure to obtain a yellow oily substance, separate and purify by flash column chromatography to obtain a white solid Product, yield: 69.6%, melting point (mp): 123.9-126.1°C.

[0058] 1 H NMR (CDCl 3 , 500MHz) δ : 7.21~7.23(m, 2H), 7.00~7.02(m, 2H), 6.95~6.97(m, 2H), 6.83~6.85(m, 2H), 4.79(s, 2H, CH 2 ), 3.79(s, 3H, OCH 3 ), 2.88(s, 3H, CH 3 ), 2.75(s, 3H, CH 3 ). 13 C NMR (CDCl 3, 125MHz) δ : 158.77, 158.09, 155.24, 150.05, 135.61, 133.74, 129.93(2C), 129.33(2C), 121.24(2C), 114.93(2C), 55.30, 52.53, 27.54, 27.40. ...

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Abstract

The invention belongs to the technical field of pesticide and particularly relates to a urea carbamate methyl substituted arly ester compound with bactericidal activity. The urea carbamate methyl replaced arly ester comprises N-methyl carbamate 4-(N-methyl-N'-arly ureido methyl) phenyl ester and N-methyl carbamate 2-(N-methyl-N'-arly ureido methyl) phenyl ester, and the constitutional formulas ofthe compound are respectively shown in a formula (I) and a formula (II). In the formula (I) and the formula (II), a benzene ring connected with an N atom has a substituent R, and the R can be H, 4-CH3, 4-CH3O, 4-Cl, 2-CH3, 2-CH3O, 2-Cl and 3-Cl. The compound can be applied to germ prevention and control of crops and is simple to synthesis, in addition, the used raw materials are easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of pesticides, in particular to a carbamate carbamate substituted aryl ester compound with bactericidal activity. Background technique [0002] Since the discovery of carbaryl with excellent insecticidal activity in 1958, carbamate pesticides have developed rapidly and become one of the three traditional insecticides, playing a very important role in agricultural protection and pest control. At present, there are more than 50 kinds of carbamate compounds used as pesticides, including insecticides, acaricides, herbicides and fungicides. The development of carbamate insecticides has roughly gone through three stages. In the early 1960s, since carbaryl was developed, many new agents have been developed, such as: Zikewei, methcarb and This is the period with the most species emerging and the fastest development. This stage is called the first development stage of carbamate insecticides. In the late 1960s, oxi...

Claims

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Application Information

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IPC IPC(8): C07C275/28C07C275/34C07C275/30C07C273/18A01P3/00
Inventor 唐子龙张超逸刘汉文常书红朱中华
Owner HUNAN UNIV OF SCI & TECH
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