3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-decyl-3-alkene-4-ol derivative

A technology of o-methylphenyl and alcohol derivatives, applied in the direction of biocides, chemicals for biological control, biocides, etc., to achieve the effect of preventing infringement

Active Publication Date: 2010-12-29
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many pests, pest mites, and germ control agents on the market, due to the continuous expansion of the market, the resistance of pests, pest mites, and diseases, the service life of drugs, and the econ

Method used

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  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-decyl-3-alkene-4-ol derivative
  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-decyl-3-alkene-4-ol derivative
  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-decyl-3-alkene-4-ol derivative

Examples

Experimental program
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Example Embodiment

Example 1

This example illustrates the preparation method of compound 01 in Table 1.

Preparation of 2-methylthio-2 methyl propionyl chloride

Preparation of 2-methylthio-2 methyl propionyl chloride

Under stirring at room temperature, add 2-chloropropionic acid (4.63g) dropwise to 6% NaHCO 3 (60ML) in the aqueous solution, react until there are no bubbles in the solution, remove most of the water on the rotary evaporator to obtain an aqueous solution of sodium 2-chloropropionate, and then add dimethylformamide (DMF, 20mL) and 20% sodium methyl mercaptan (20ML) aqueous solution, heated to 80℃, stirred for 10-20 hours, cooled to room temperature and slowly poured into water (20-50ML), acidified with 2N hydrochloric acid to PH=3-4, ethyl acetate Ester extraction, washing organic phase, anhydrous NaSO 4 After drying and concentrating on a rotary evaporator, 3.96 g of 2-methylthiopropionic acid liquid was obtained with a yield of 76%.

The preparation of 2-methylthiopropionyl chlori...

Example Embodiment

Example 2

This example illustrates the preparation method of compound 02 in Table 1.

3-(2-Methylphenyl)-2-oxo-1-oxaspiro[4,5]-dec-3-en-4-yl-2-methylthio-2-methylpropionate Synthesis (No.03 in Table 1)

Add 3-(2-methylphenyl)-2-oxo-1-oxaspiro[4,5]-dec-3-ene into a 100mL three-necked flask equipped with a magnetic stirrer, thermometer and condenser -4-ol (0.50g), dichloromethane (40ml) and triethylamine (0.3g), fully dissolve and stir, add dropwise chloropivaloyl chloride (0.42) dissolved in dichloromethane (10ML) under ice bath conditions g) After dripping, react at room temperature for 3-5 hours. The reactants are washed with water, saturated brine, dried over anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography (petroleum ether: ethyl acetate 10:1) to obtain the title compound 0.32 g, the content is 94.5%, and the yield is 41.4%. Melting point of white solid: 97.1~98.8℃. 1 HNMR(CDCl 3 ) 1.161(s, 6H, 2CH 3 ), 1.791 (m, 10H, cyclohexane)...

Example Embodiment

Example 3

This example illustrates the preparation method of compound 03 in Table 1.

Preparation of 2-methylthio-2 methyl propionyl chloride

Preparation of 2-Methylthio-2 Methylpropionic Acid To a 100 mL three-necked flask equipped with a thermometer, condenser, and constant pressure dropping funnel, add 20% sodium methyl mercaptan aqueous solution (41.2 g), under ice water bath, After dissolving 2-bromo-2-methylpropionic acid (6.68g) in 20mL of water, add it dropwise to the above solution. After 25min, the addition is complete. After reacting at 10~15℃ for 3h, react at room temperature overnight. After the reaction is complete , 20Ml concentrated hydrochloric acid was slowly added dropwise, adjusted to Ph=3~4, the reaction mixture was extracted three times with 20mL ether and twice with 20mL chloroform, the organic layers were combined, and anhydrous NaSO 4 After drying and concentrating on a rotary evaporator, 4.01 g of light yellow liquid was obtained, with a yield of 75.0%...

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Abstract

The invention discloses a 3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-decyl-3-alkene-4-ol derivative with insecticidal, acaricidal and antifungal biological activities and a preparation method thereof, wherein R is a substituent shown as the description.

Description

technical field The present invention relates to 3-o-methylphenyl-2-oxo-1-oxaspiro[4,5]-dec-3-en-4-ol derivatives with insecticidal, acaricidal and fungicidal biological activities and their preparation methods. Background technique The control of pests, harmful mites and pathogens is very important in the process of realizing efficient agriculture. At the same time, the control of pests, harmful mites, and germs is also very important in forestry, animal husbandry, sideline, fishery, and public health. Although there are many pests, pest mites, and germ control agents on the market, due to the continuous expansion of the market and the problems of resistance to pests, pest mites, and diseases, the service life of drugs, and the economics of drugs and people's increasing emphasis on the environment , Scientists need to continue to study, and then develop new efficient, safe, economical and different types of insecticides, acaricides, and fungicides. Bayer company disclos...

Claims

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Application Information

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IPC IPC(8): C07D307/94A01N43/12A01P7/02A01P7/04A01P3/00
CPCA01N43/12A01N47/06C07D307/94A01N53/00
Inventor 王晓光柳爱平裴晖祝小星刘兴平喻快胡礼刘卫东刘民华毛冠群
Owner HUNAN CHEM RES INST
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