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Preparation and plant activate antipathogen activity of benzo carboxylate derivatives of 1,2,3-thiadiazole

A technology of thiadiazole and derivatives, applied in the field of plant activation and disease resistance activity, can solve the problems of unsatisfactory water solubility and slow action speed, and achieve the effects of good water solubility, disease resistance activity, and damage prevention.

Inactive Publication Date: 2012-10-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But as this kind of compound they have obvious disadvantages: namely, their water solubility is not very ideal, so that its action speed is slow, and it needs to be made into various preparations, such as benzo[1,2,3]thiadiazole- 7-Carboxylic acid is insoluble in water, slightly soluble in organic solvents, it needs to be made into emulsion, suspension
Very hydrophilic drugs cannot pass through the lipid layer of the biomembrane, while very hydrophobic drugs remain as part of the biomembrane for similar and compatible reasons, so they cannot effectively enter the inner cytoplasm

Method used

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  • Preparation and plant activate antipathogen activity of benzo carboxylate derivatives of 1,2,3-thiadiazole
  • Preparation and plant activate antipathogen activity of benzo carboxylate derivatives of 1,2,3-thiadiazole
  • Preparation and plant activate antipathogen activity of benzo carboxylate derivatives of 1,2,3-thiadiazole

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Embodiment Construction

[0045] The following examples and bioassay results can be further used to illustrate the plant-activated disease resistance activity of the compounds of the present invention, but are not meant to limit the present invention.

[0046] Synthetic example

[0047] Synthesis of compound 1

[0048] 1. Preparation of benzo[1,2,3]-thiadiazole-7formyl chloride

[0049] Add 1.80 g (0.01 mol) of benzo[1,2,3]-thiadiazole-7-carboxylic acid and 10 ml of thionyl chloride into a 50 ml round-bottomed flask, heat and reflux at 80-90°C for 8 hours, Evaporate excess thionyl chloride under reduced pressure to obtain a brownish-yellow solid, and the intermediate benzo[1,2,3]-thiadiazole-7-formyl chloride is sealed and stored in a vacuum desiccator for subsequent use. The amount of the compound can be scale up or down accordingly.

[0050] 2. Compound 1: Synthesis of benzo[1,2,3]-thiadiazole-7-carboxylic acid (N,N-dimethyl)ethyl ester

[0051] Add 3.60 g (0.02 moles) of benzo[1,2,3]-thiadiazole...

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Abstract

The invention provides water-oil soluble benzo[1,2,3]-thiadiazole-7-carboxylate derivatives with plant activate antipathogen activity and salts thereof. The derivatives are shown as a general formula (I, II), wherein X is an oxygen, a nitrogen atom or a sulfur atom; n is 0, 1, 2, 3, 4, 5 and so on or (CH2)n represents alkyl carrying a branched chain; Y is Cl<->, Br<->, F<->, I<->, AcO<->, acetylsalicylic acid radical, nitric acid radical, salicylic acid radical, p-toluenesulfonic acid radical, bisulfate radical or other negative ions; R<1> is alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, or aryl; R<2> is alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, alkenyl of 1-6 atoms, or aryl; or the R<1> and the R<2> are selected from the structure in the specification.

Description

technical field [0001] The invention relates to the preparation of benzocarboxylate derivatives of 1,2,3-thiadiazole and the activation of disease-resistant activity in plants. Background technique [0002] 1,2,3-thiadiazole heterocyclic compounds have a wide range of biological activities (Bakulev V A, Dehaen W. The Chemistry of 1,2,3-thiadiazole, 2004, John Wiley & Sons.Inc.), have been successfully developed There are three compounds in the pesticide products including BTH and thiazil (TDL) and TDZ is a derivative of 1,2,3-thiadiazole, BTH and TDL are typical plant activators, of which BTH is the first to develop A successful artificially synthesized plant activator, it is a product of Syngenta, and is currently the most successfully developed compound with the best inducing activity. Benzo[1,2,3]thiadiazole-7-carboxylate methyl ester (BTH) and its derivatives have been reported in some documents, and Walter Kunz of Ciba-Geigy Co., Ltd. is researching and developing sulf...

Claims

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Application Information

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IPC IPC(8): C07D285/14A01N43/828A01P21/00A01P3/00
Inventor 邹小毛王瑞花李伟刘殿甲傅翠蓉杨华铮丁会娟臧福坤单鹏程刘俊黄纯陈森
Owner NANKAI UNIV
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