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Benzo [1,2,3] thiadiazole derivative its synthesis method and use

A technology of benzothiadiazole and synthetic method, which is applied in the fields of biocides, chemicals for biological control, organic chemistry, etc., can solve the problem of inducing tobacco anti-tobacco mosaic virus activity, unreported synthetic method and Screening results of induced disease resistance activity, no screening of induced disease resistance biological activity, etc., to achieve a good induction effect

Inactive Publication Date: 2006-06-14
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Among the benzothiadiazole derivatives disclosed in domestic and foreign patent documents, except for the patents applied by the applicants themselves, none of them involve the activity of inducing tobacco anti-tobacco mosaic virus (abbreviated as TMV), nor have relevant inductive anti-tobacco In order to further search for new BTH derivatives with higher inductive activity and lay the foundation for the study of structure-activity relationship (QSAR), the patent of this invention further carried out structural modification on the basis of previous research, and synthesized 20 There is no new compound reported in the literature. We cultured single crystal of BLLB14 and reported its single crystal structure (Bao Lili, Fan Zhijin, Song Haibin, Nie Kaisheng. N-Phenyl-N′-(1,3 -thiazol-2-yl)-1,2,3-benzothiadiazole-7-carboxamidine.Acta Crystallographica E, 61(11):o3817~o3818.), but the synthesis method and screening results of inducing disease resistance activity were not reported

Method used

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  • Benzo [1,2,3] thiadiazole derivative its synthesis method and use
  • Benzo [1,2,3] thiadiazole derivative its synthesis method and use
  • Benzo [1,2,3] thiadiazole derivative its synthesis method and use

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Experimental program
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Effect test

Embodiment 1

[0036] Preparation of benzo[1,2,3]thiadiazole-7-carbonyl chloride:

[0037] Add 27.0g of benzo[1,2,3]thiadiazole-7-carboxylic acid, 200mL of anhydrous toluene, 1mL of DMF, and 20mL of SOCl in a 500mL three-neck flask 2 , slowly raise the temperature to 80-90°C, keep this temperature and continue to react for 6 hours, filter after cooling, and desolvate the filtrate under reduced pressure to obtain 28g of the product benzo[1,2,3]thiadiazole-7-carbonyl chloride, the product does not need Purified and stored in a desiccator for direct use in the next reaction.

Embodiment 2

[0039] Synthesis and structure identification of compound B2:

[0040] Add 0.47g of 2-aminopyridine, 25mL of absolute anhydrous tetrahydrofuran and 0.32g of sodium hydride into a 100mL three-necked flask to prepare the sodium salt suspension of the corresponding amine, stir at room temperature for 1.5 hours, and dropwise add 1g of benzo[1,2,3] Thiadiazole-7-carbonyl chloride in 15 mL absolute anhydrous tetrahydrofuran solution, stirred at room temperature for 2 hours, filtered after the reaction, desolvated under reduced pressure to obtain 0.52 g of crude product, yield 41.1%, purified by silica gel column chromatography to obtain pure product , the eluent used is petroleum ether and ethyl acetate at 60-90° C., and their volume ratio is 2:1. Determination of melting point and 1 H NMR, its chemical structural formula and physical and chemical parameters are shown in Table 1 and Table 2, as seen from Table 1 and Table 2, this compound 1 H NMR shows the chemical shift correspon...

Embodiment 3

[0042] Synthesis and structure identification of compound B4:

[0043] Add 0.50g of 2-aminothiazole, 25mL of absolute anhydrous tetrahydrofuran and 0.23g of sodium hydride into a 100mL three-necked flask to prepare the sodium salt suspension of the corresponding amine, stir at room temperature for 1.5 hours, and dropwise add 1g of benzo[1,2,3] Thiadiazole-7-carbonyl chloride in 15 mL absolute anhydrous tetrahydrofuran solution, stirred at room temperature for 2 hours, filtered after the reaction, and precipitated under reduced pressure to obtain 0.71 g of crude product, yield 54.2%, purified by silica gel column chromatography to obtain pure product , the eluent used is petroleum ether and ethyl acetate at 60-90° C., and their volume ratio is 5:1. Determination of melting point and 1 H NMR, its chemical structural formula and physical and chemical parameters are shown in Table 1 and Table 2, as seen from Table 1 and Table 2, this compound 1 H NMR shows the chemical shift cor...

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Abstract

The present invention provides a kind of benzothiobiazole substituent formamidine derivative and benzothiobiazole methanamide derivative, their synthesis method and application. Said invention also provides their structure formulae in which 10 formamidine derivatives containing benzo [1,2,3] thiobiazole substituent and 10 substituted benzo [1,2,3] thiobiazole-7-methanamide derivatives. These compounds have the activity for resisting tobacco mosaic virus and inducing tobacco to resist tobacco mosaic virus and microbiostatic action for inhibiting agricultural fungi.

Description

technical field [0001] The technical solution of the present invention relates to a 1,2-oxadiazole-containing heterocyclic compound fused with a carbocycle, in particular to a benzothiadiazole derivative. Background technique [0002] The plant-induced disease resistance activator has a novel mechanism of action, is environmentally friendly, and belongs to the category of green pesticides. The main varieties that have been successfully researched and developed are S-methylbenzo[1,2,3]thiadiazole-7-thiocarboxylate Ester (English abbreviation is BTH, English common name: acibenzolar-S-methyl), 2,6-dichloroisonicotinic acid and β-aminobutyric acid, methyl jasmonate, allyl isothiazole and thiazamide ( Common name in English: Tiadinil, referred to as TDL), etc. (Bao Lili, Liu Fengli, Fan Zhijin, Lead compounds with plant-induced disease resistance activity and their structural modifications, Acta Pesticide Science, 2005, 7(3): 201-209; Michiko Yasuda; Hideo Nakashita ; Shigeo Yo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/14A01P3/00C07D417/12
Inventor 范志金鲍丽丽刘秀峰范志银张永刚苑建勋聂开晟石祖贵
Owner NANKAI UNIV
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