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N, S-containing heterocyclic compound with nematicidal activity, preparation method and application thereof

A compound and heterocyclic technology, which is applied in the field of pesticides, can solve the problems of secondary infection by pathogens, plundering of host plants, and increasing difficulty in nematode control.

Inactive Publication Date: 2014-08-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Plant parasitic nematodes are extremely harmful to plants. They can parasitize almost any part of the plant. They can cause mechanical damage to the host plant through feeding activities and plunder the nutrition of the host plant. In particular, their esophageal gland secretions can cause host plants to develop A series of pathological changes will also spread other pathogens or promote the secondary infection of other pathogens, causing diseases of host plants and resulting in yield loss
Globally, the harm of plant parasitic nematodes is becoming more and more serious, usually causing crop yield reduction of 10-40%, and causing economic losses of up to 80-100 billion U.S. dollars every year, which seriously limits the development of agricultural economy
[0003] At present, the control of nematodes in agriculture is mainly based on chemical control. The widely used chemical nematicides include aldicarb, thifamifos, carbofuran, profenphos, fenamiphos, thiazophos, thiazophos and Terbuphos, etc., which are highly toxic and highly residual organophosphorus or carbamate pesticides, have low safety to humans and non-target organisms, and will also cause pollution to soil, water sources and agricultural products
In addition, the excessive and frequent use of such nematicides has caused serious drug resistance, making the control of nematodes more difficult.

Method used

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  • N, S-containing heterocyclic compound with nematicidal activity, preparation method and application thereof
  • N, S-containing heterocyclic compound with nematicidal activity, preparation method and application thereof
  • N, S-containing heterocyclic compound with nematicidal activity, preparation method and application thereof

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preparation example Construction

[0117] The preparation method of the compound of the present invention

[0118] The compound represented by the general formula (I) of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactant, solvent, base, compound used, reaction temperature, reaction time required, etc. are not limited to the following explanations . The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0119] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at a reaction temperature of 0-60°C (preferably 20-40°C). The reaction time is usually 2-24 hours, preferably 4-12 hours.

[0120] The base used in the reaction includes (but is not limited t...

Embodiment 1

[0146] Example 12-(1-cyano-1-methyl carboxylate)-3-N-(2-fluorophenyl)-1,3-thiazol-4-one

[0147] 1.1 Preparation of 2-fluorophenylisothiocyanate

[0148]

[0149] Add 1.11g (10mmol) of 2-fluoroaniline and 3.36g of triethylenediamine (30mmol) into 15ml of acetone, stir to dissolve them, add dropwise 45ml of carbon disulfide, and stir the reaction at room temperature. The reaction was tracked by TLC. After the reaction of 2-fluoroaniline was complete, it was filtered and dried to obtain a powdery solid. It was added in 30ml chloroform, stirred to make it into a suspension, down to 0°C, slowly added dropwise 10ml chloroform solution of 0.99g (3.34mmol) bis(trichloromethyl)carbonate (BTC), added, The temperature was raised to room temperature for reaction, followed by TLC. After the reaction, the insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure to obtain 1.23 g of a yellow solid, which was directly used in the next step without...

Embodiment 2

[0153] Example 22-(1-cyano-1-methyl carboxylate)-3-N-(4-nitrophenyl)-1,3-thiazol-4-one

[0154]

[0155] The preparation method of 4-nitrophenyl isothiocyanate is similar to step 1.1 of Example 1, except that 4-nitroaniline is used instead of 2-fluoroaniline.

[0156] Add 0.56g (10mmol) potassium hydroxide to 20ml DMF, stir to make it into a suspension, add 0.5 g (5mmol) methyl cyanoacetate, be down to 0 ℃, dropwise add the 5ml DMF solution of 0.9g (5mmol) 4-nitrophenyl isothiocyanate, add, be warming up to room temperature reaction. The reaction was tracked by TLC. After the reaction of 4-nitrophenylisothiocyanate was complete, the temperature was lowered to 0°C, and 0.565 g (5 mmol) of chloroacetyl chloride was slowly added dropwise. After the addition was completed, the temperature was raised to room temperature for 8 hours. The reaction solution was poured into ice water, a large amount of yellow solids were precipitated, filtered, and recrystallized from ethyl acetate...

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Abstract

The invention relates to an N, S-containing heterocyclic compound with nematicidal activity, a preparation method and application thereof. Specifically, the invention discloses a compound as formula (I) or optical isomers, cis-trans-isomers of the compound or agricultural pharmacology acceptable salts, and the preparation method thereof. The invention also discloses agricultural compositions containing the compound and application thereof. The compound has excellent nematicidal activity. (formula I).

Description

technical field [0001] The invention belongs to the field of pesticides. Specifically, the present invention relates to a compound containing N, S heterocyclic structure with nematicide activity and its preparation method and application. Background technique [0002] Plant parasitic nematodes are extremely harmful to plants. They can parasitize almost any part of the plant. They can cause mechanical damage to the host plant through feeding activities and plunder the nutrition of the host plant. In particular, their esophageal gland secretions can cause host plants to develop A series of pathological changes will also spread other pathogens or promote the secondary infection of other pathogens, causing diseases of host plants and resulting in yield loss. Worldwide, the harm of plant parasitic nematodes is becoming more and more serious, usually causing 10-40% crop yield reduction, and causing economic losses as high as 80-100 billion US dollars every year, which seriously l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/34C07D279/06C07D417/06C07D417/04C07D471/04A01N43/78A01N47/30A01N43/86A01N43/90A01N47/36A01P5/00
CPCC07D417/14A01N43/78A01N43/86A01N43/90A01N47/30A01N47/36C07D277/30C07D277/34C07D279/06C07D417/04C07D417/06C07D471/04
Inventor 徐晓勇李忠李春燕王高磊廖聘宋恭华邵旭升须志平
Owner EAST CHINA UNIV OF SCI & TECH
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