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A trans-structured lactone ring-containing nematocide and its preparation method and use

A technology of nematicides and lactone rings, applied in the field of nematicides containing lactone rings and its preparation, can solve the problems of high toxicity, phytotoxicity of crops, affecting use, etc., and achieve less harmfulness, less residue, Good insecticidal effect

Active Publication Date: 2017-09-19
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Compared with nematicides and fungicides, there are only a dozen special-purpose nematicides with better effects in the world at present, and because the existing nematicides with better effects are highly toxic to humans and animals, Some species have phytotoxicity to crops, affecting their use, so new, efficient and environmentally friendly nematicides need to be developed urgently

Method used

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  • A trans-structured lactone ring-containing nematocide and its preparation method and use
  • A trans-structured lactone ring-containing nematocide and its preparation method and use
  • A trans-structured lactone ring-containing nematocide and its preparation method and use

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preparation example Construction

[0031] Preferably, a trans-structured lactone ring-containing nematicide, R 2 =R 4 = CF 3 when R 1 =R 3 =R 5 =H. The present invention also provides a preparation method of a trans-structured lactone ring-containing nematicide, comprising the following steps:

[0032] ① The acid with cis-trans racemization Add to sulfuric acid solution with a volume fraction of 40-70%, stir at 50-70°C for 3-5 hours, filter, add the filter cake to ethyl acetate and water, extract and collect the organic phase, dry the organic phase over magnesium sulfate, and evaporate the solvent , recrystallized from toluene and dried to give the trans-structured acid

[0033] ② will and the acid of the trans structure obtained in step 1. Add to the solvent, add the acid binding agent, stir and react at 20-30°C for 22-26 hours, under the vacuum of 0.08-0.10kPa, distill off the solvent, add dichloromethane and water and stir evenly, let stand to separate and remove water , under the vacuum degre...

Embodiment 1

[0052] The compound of serial number 2 in the preparation table 1 comprises the following steps:

[0053] ①Add 1mol of o-tolualdehyde, 0.8mol of succinic anhydride and 1mol of anhydrous zinc chloride into 300ml of dichloromethane, add 3mol of triethylamine dropwise at 0°C, and the reaction solution is obtained after the addition is completed, and the reaction solution is placed in Stir at 20°C for 10 hours, add hydrochloric acid therein to adjust the pH of the reaction solution to 2, add 200ml of ethyl acetate for extraction, collect the organic phase, add 200ml of toluene to the organic phase for recrystallization to obtain 5-oxo-2-(2-methyl phenyl)tetrahydrofuran-3-carboxylic acid;

[0054] ②Add 5-oxo-2-(2-methylphenyl)tetrahydrofuran-3-carboxylic acid obtained in step ① into 40% sulfuric acid solution, stir at 50°C for 3h, filter, and add the filter cake to ethyl acetate and water , extract and collect the organic phase, dry the organic phase over magnesium sulfate, evapor...

Embodiment 2

[0059] The compound of sequence number 26 in the preparation table 1 comprises the following steps:

[0060] ① Add 1mol of 4-fluoro-5-phenoxybenzaldehyde, 1.2mol of succinic anhydride and 3mol of anhydrous zinc chloride into 400ml of dichloromethane, add 5mol of triethylamine dropwise at 5°C, and the reaction solution is obtained after the dropwise addition is completed. Stir the reaction solution at 30°C for 20 hours, add hydrochloric acid to adjust the pH of the reaction solution to 2, add 250ml of ethyl acetate for extraction, collect the organic phase, add 250ml of toluene to the organic phase for recrystallization to obtain 5-oxo-2 -(2-(4-fluoro-5-phenoxy)phenyl)tetrahydrofuran-3-carboxylic acid;

[0061] ②Add 5-oxo-2-(2-(4-fluoro-5-phenoxy)phenyl)tetrahydrofuran-3-carboxylic acid obtained in step ① into 70% sulfuric acid solution, stir at 40°C for 5h, filter, Add the filter cake to ethyl acetate and water, extract and collect the organic phase, dry the organic phase ove...

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Abstract

Disclosed is a nematicide of trans structure containing a lactone ring, characterized in that the general structural formula I is as shown in (I). R1, R2, R3, R4 and R5 are selected from hydrogen, cyano, fluorine, chlorine, bromine, an alkyl containing 1 to 4 carbon atoms, an alkoxy containing 1 to 4 carbon atoms, alkoxyphenyl, an alkoxy containing 1 to 4 carbon atoms and a hydrogen atom on the carbon atom substituted by one or more chlorine atoms, an alkoxy containing 1 to 4 carbon atoms and a hydrogen atom on the carbon atom substituted by one or more fluorin atoms, nitro or amino; R6 is selected from hydrogen, fluorine and chlorine; the nematicide of trans structure containing the lactone ring is used for controlling agricultural nematode diseases; because the nematicide of trans structure containing the lactone ring comprises the structure of a polyfluorobutene and a lactone ring, the nematicide has a good control effect on eggs and the second-stage juveniles of a root-knot nematodes, and in particular can fully inhibit the hatching of crop root-knot nematode eggs; and same has a low toxicity, and less residue in crops, thus improving the safety of agricultural production.

Description

technical field [0001] The invention relates to the technical fields of agrochemicals and medicines, in particular to a trans-structured lactone ring-containing nematicide and its preparation method and application. technical background [0002] Most of the nematodes live in the soil, some are parasitic in the plants, spread through the soil or seeds, can damage the root system of plants, or invade the organs of the above-ground parts, affect the growth and development of crops, and indirectly spread diseases caused by other microorganisms, causing agricultural pollution. huge economic losses. Existing nematicides penetrate through the epidermis of nematodes to kill nematodes. [0003] Compared with nematicides and fungicides, there are only a dozen special-purpose nematicides with better effects in the world at present, and because the existing nematicides with better effects are highly toxic to humans and animals, Some species have phytotoxicity to crops, affecting their...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/33A01N43/08A01P5/00
CPCA01N43/08C07D307/33
Inventor 唐剑峰潘光民刘杰赵恭文吴建挺李冬蓉牛芳
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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