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3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-n-3-ene-4-alcohol and derivatives thereof

A technology of o-methylphenyl and oxaspiro, applied in biocides, chemicals for biological control, biocides, etc., to prevent crops from being attacked by insects and/or mites

Active Publication Date: 2012-12-12
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 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, miticides, and fungicides

Method used

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  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-n-3-ene-4-alcohol and derivatives thereof
  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-n-3-ene-4-alcohol and derivatives thereof
  • 3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-n-3-ene-4-alcohol and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] This example illustrates the preparation method of compound 01 in Table 1.

[0056]

[0057] Preparation of 1-cyanocyclopentanol (IV-b) Add cyclopentanone (20.0g) to a three-necked flask equipped with a constant pressure dropping funnel, a thermometer, and mechanical stirring, turn on the stirring, and control the temperature in an ice bath -10 ℃~15℃, respectively add potassium cyanide (18.6g dissolved in 34mL water) and sodium bisulfate (29.7g dissolved in 36mL water), at -10℃~15℃, first add one third of cyanide dropwise Sodium aqueous solution, and then one third of sodium bisulfate aqueous solution is added dropwise, the dropping time is 15 minutes respectively, the pH value of the reaction system is monitored 3-4, and the reaction is stirred for 1 hour, and then the above operation is repeated twice. Separate the layers, extract three times with ethyl acetate, combine the organic layers, and anhydrous NaSO 4 After drying and concentrating on a rotary evaporator, 19.6 g...

Embodiment 2

[0063] This example illustrates the preparation method of compound 02 in Table 1.

[0064]

[0065] Synthesis of 3-(2-methylphenyl)-2-oxo-1-oxaspiro[4,4]-non-3-en-4-yl-chloropivalate (No in Table 1 .02) In a 100 mL three-necked flask equipped with a magnetic stirrer, a thermometer and a condenser, was added 3-(2-methylphenyl)-2-oxo-1-oxaspiro (prepared by the method of Example 1). 4,4]-non-3-en-4-ol (0.49g), dichloromethane (40ml) and triethylamine (0.3g), fully dissolved and stirred, and dissolved in dichloromethane ( 10ML) chloropivaloyl chloride (0.42g), after dripping, react at room temperature for 3-5 hours, wash the reactants with water, saturated brine, dry with anhydrous magnesium sulfate, concentrate, and purify by silica gel column chromatography (petroleum ether: acetic acid Ethyl ester 10:1) to obtain 0.35 g of the title compound, with a content of 95.5% and a yield of 45.8%. Melting point of white solid: 95.5~98.2℃. 1 H NMR(CDCl 3 )1.171(s, 6H, C(CH 3 ) 2 ), 1.847-...

Embodiment 3

[0067] This example illustrates the preparation method of compound 03 in Table 1.

[0068]

[0069] Preparation of 2-Methylthiopropionic acid Under stirring at room temperature, 2-chloropropionic acid (4.63g) was added 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%.

[0070] The preparation of 2-methylthiopropionyl chloride was added to a 100mL single-necked flask wit...

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Abstract

Disclosed are 3-ortho-methylphenyl-2-oxo-1-oxaspiro[4,4]non-3-en-4-ol of formula (I), derivatives and preparation method thereof, wherein (II) is described as the description. The compounds of formula (I) can be used as pesticides, acaricides and fungicides.

Description

technical field [0001] The present invention relates to 3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-non-3-en-4-ol with insecticidal, acaricidal and fungicidal biological activities and its Derivatives and methods for their preparation. Background technique [0002] 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 fungic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94A01N43/12A01P7/02A01P7/04A01P3/00
CPCA01N43/12A01N47/06C07D307/94A01N53/00
Inventor 柳爱平任叶果黄路裴晖胡志彬林雪梅成四喜黄明智祝小星韦天龙
Owner HUNAN CHEM RES INST