Preparation method for novel insecticide indoxacarb

A technology of indoxacarb and insecticide, which is applied in the field of preparation of new insecticide indoxacarb, can solve problems such as danger, and achieve the effects of good purity, good product purity and high yield

Inactive Publication Date: 2014-12-10
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention adopts the production technology of green cleaning process, that is, protects with fluorenylmethoxycarbonyl chloride, deprotects in alkaline solution, and then reacts with methyl (chlorocarbonyl)[4-(trifluoromethoxy)phenyl]carbamate The method for preparing indoxacarb by condensation

Method used

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  • Preparation method for novel insecticide indoxacarb
  • Preparation method for novel insecticide indoxacarb

Examples

Experimental program
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Effect test

example 1

[0021] Example 1: Preparation of hydrazine carboxylate fluorene methyl ester

[0022] 80% hydrazine hydrate (24.5g, 0.40mol) was added to a 500mL reaction flask, and a solution of Fmoc-Cl (51.8g, 0.20mol) in tetrahydrofuran (280ml) was added dropwise at -20°C. After the dropwise addition was completed in about 2 hours , then continue to stir for 30min, stop the reaction, pour it into a separatory funnel, stand still, separate the upper organic layer, evaporate the solvent under reduced pressure, cool the residue, and filter to obtain the crude hydrazine carboxylic acid fluorene methyl ester, which is washed with ethyl acetate. After recrystallization, 32.7 g of hydrazine carboxylate fluorene methyl ester was obtained as white needle crystals. Yield: 85.7%, melting point: 168-170°C. 1 HNMR(DMSO)δ(ppm): 4.05(s, 2H), 4.16-4.31(m, 3H), 7.31(t, 2H, J=7.3Hz), 7.40(t, 2H, J=7.3Hz), 7.67 (d, 2H, J=7.3 Hz), 7.86 (d, 2H, J=7.3 Hz), 8.36 (s, 1H).

example 2

[0023] Example 2: Preparation of hydrazine carboxylate fluorene methyl ester

[0024]80% hydrazine hydrate (26.8g, 0.60mol) was added to a 500mL reaction flask, and a solution of Fmoc-Cl (51.8g, 0.20mol) in tetrahydrofuran (360ml) was added dropwise at -10°C, and the dropwise addition was completed within about 2 hours. , and then continue to stir for 60 min, stop the reaction, pour it into a separatory funnel, stand still, separate the upper organic layer, remove the solvent by distillation under reduced pressure, cool the residue, and filter to obtain the crude hydrazine carboxylate fluorene methyl ester, which is washed with ethyl acetate. After recrystallization, 33.2 g of hydrazine carboxylate fluorene methyl ester was obtained as white needle crystals. Yield: 87.0%.

example 3

[0025] Example 3: Preparation of (+)[5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-ylidene]hydrazine carboxylate fluorene methyl ester

[0026] Into a 500mL reaction flask, add (+) methyl 5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-indene-2-carboxylate (24.1g, 0.10mol), hydrazine carboxylic acid Fluorene methyl ester (25.3 g, 0.10 mol), p-toluenesulfonic acid (3.0 g, 0.015 mol) and methanol (250 ml). Heated reflux reaction for 20h, after the reaction,

[0027] Cool and filter to obtain) [5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-idene] hydrazine carboxylic acid fluorene methyl ester crude product, recrystallize from methanol, filter , dried in vacuo to give a white solid [5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-idene]hydrazine carboxylate fluorene methyl ester 39.5g, yield For 82.8%, melting point: 172-174 ℃. 1 HNMR (CDCl 3 ), δ(ppm): 3.633(d, 1H, J=5.7Hz), 3.812(d, 1H, J=5.7Hz), 4.122(s, 3H), 4.532(m, 1H), 4.754(m, 2H) ), 7...

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Abstract

The invention discloses a preparation method for a novel insecticide indoxacarb. The preparation method comprises the following steps: taking (+)5-chlorine-1,3-dihydro-2-hydroxyl-1-oxo-2H-indene-methyl carboxylate and 4-(trifluoromethoxy)benzenaime as raw materials, protecting (+)5-chlorine-1,3-dihydro-2-hydroxyl-1-oxo-2H-indene-methyl carboxylate by virtue of fluorenylmethyl chloroformate, and carrying out cyclization to prepare 2-( fluorenylmethyl)-7-chlorinindene-[1,2-e][1,34]] oxadiazine-2,4a(3H, 5H)-dicarboxylic acid-4a-methyl ether; reacting trifluoromethoxyaniline and methylchloroformate with phosgene to prepare (chlorocarbonyl)[4-(trifluoromethoxy)phenyl] methyl carbamate; carrying out deprotection on 2-( fluorenylmethyl)-7-chlorinindene-[1,2-e][1,34]] oxadiazine-2,4a(3H, 5H)-dicarboxylic acid-4a-methyl ether in alkaline solution and then carrying out condensation reaction with (chlorocarbonyl)[4-(trifluoromethoxy)phenyl] methyl carbamate to prepare the indoxacarb. The process yield of the indoxacarb is high and the purity of the indoxacarb is good.

Description

technical field [0001] The invention relates to a preparation method of a novel insecticide indoxacarb, in particular to a preparation method with (+)5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-indene-2 -Methyl carboxylate (formula 2) and p-trifluoromethoxyaniline (formula 7) as raw materials, through fluorene methoxycarbonyl chloride (formula 3) protection, cyclization carbonylation and other reactions to prepare key two key intermediates 2 -(Fluorenylmethyl)-7-chloroindeno[1,2-e][1,3,4]]oxadiazine-2,4a(3H,5H)-dicarboxylic acid-4a-methyl ester ( formula 5) and methyl (chlorocarbonyl)[4-(trifluoromethoxy)phenyl]carbamate (formula 9), which are then combined with (chlorocarbonyl)[4-(trifluoromethoxy) through deprotection A method for preparing indoxacarb by condensation reaction of methyl phenyl]carbamate (Formula 9) belongs to the field of agricultural chemistry. Background technique [0002] According to the statistics of the World Food and Agriculture Organization, the loss ...

Claims

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Application Information

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IPC IPC(8): C07D273/04
CPCC07D273/04
Inventor 徐德锋柳丽
Owner CHANGZHOU UNIV
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