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A class of 4,5-dihydrothiadiazole alkylate derivatives containing 4-methyl-1,2,3-thiadiazole and its preparation method and use

A kind of dihydrothiadiazole alkyd ester, thiadiazole technology, applied in the field containing 1

Inactive Publication Date: 2016-03-30
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in recent years, the widespread and unscientific use of various fungicides has caused various pathogenic bacteria in my country's farmland to produce obvious resistance to existing traditional fungicides (Jia Junchao, Ma Lin, Fan Zhijin, etc. Journal of Pesticide Science, 2008 , 10(1):1-9.)

Method used

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  • A class of 4,5-dihydrothiadiazole alkylate derivatives containing 4-methyl-1,2,3-thiadiazole and its preparation method and use
  • A class of 4,5-dihydrothiadiazole alkylate derivatives containing 4-methyl-1,2,3-thiadiazole and its preparation method and use
  • A class of 4,5-dihydrothiadiazole alkylate derivatives containing 4-methyl-1,2,3-thiadiazole and its preparation method and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of intermediate 4-methyl-1,2,3-thiadiazole-5-carboxamide II:

[0041] Add 80 ml of ethanol, 5-methyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (17.2 g, 100 mmol), concentrated ammonia water (80 ml, 25 % aqueous solution), stirred at room temperature for 12 hours, cooled to 0 degrees Celsius, filtered, washed with a small amount of ethanol, and dried in vacuo to obtain 15.6 grams of white solid. The yield was calculated with the pure product obtained, and the yield was 98%; 1 HNMR (400MHz, CDCl 3 ): δ5.92 (s, br, 2H), 2.95 (s, 3H); the chemical structure and physicochemical parameters of 4-methyl-1,2,3-thiadiazole-5-carboxamide II are shown in Table 1 .

Embodiment 2

[0043] Preparation of intermediate 4-methyl-1,2,3-thiadiazole-5-thioformamide III:

[0044] Add starting reactant 4-methyl-1,2,3-thiadiazole-5-carboxamide II (14.3 grams, 100 mmoles), 150 milliliters of toluene, Lawson's reagent in 250 milliliters three-neck round bottom flask (Lawesson's Reagent) (24.2 g, 60 mmol), under nitrogen protection, stirred and refluxed for 4 hours. After the reaction was completed, the reaction solution was concentrated to remove toluene, and the residue was purified by 200-300 mesh silica gel column chromatography to obtain light yellow solid 4-formazan Base-1,2,3-thiadiazole-5-thioformamide III, the eluent is petroleum ether at 60 to 90 degrees centigrade: ethyl acetate, and the volume ratio is 3:1 depending on the product; Gained pure product calculation yield, yield 75%; 1 HNMR (400MHz, CDCl 3 ): δ6.12(s, br, 2H), 2.95(s, 3H).

Embodiment 3

[0046] Preparation of intermediate 2-(4-methyl-1,2,3-thiadiazol-5-yl)-4-(trifluoromethyl)-4,5-dihydrothiazol-4-ol IV:

[0047] Add 4-methyl-1,2,3-thiadiazole-5-thioformamide III (7.96 g, 50 mmol) and 60 ml of treated dehydrated alcohol into a 100 ml three-neck round bottom flask, 3-Bromo-1,1,1-trifluoroacetone (9.6 g, 50 mmol), stirred and refluxed under nitrogen protection for 16 hours; after the reaction, the reaction solution was concentrated to remove toluene, and the residue was subjected to 200-300 mesh silica gel column chromatography Purify to obtain 9.4 grams of light yellow solid 4-methyl-1,2,3-thiadiazole-5-thioformamide III, the eluent is petroleum ether at 60 to 90 degrees Celsius: ethyl acetate, and the volume ratio is 10: 1; Calculate the yield with the pure product obtained, and the yield is 70%; 1 HNMR (400MHz, CDCl 3 ): δ3.65(s, 2H), 3.00(s, 3H).

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Abstract

The invention provides a 4, 5-dihydro thiazole alcoholic ester derivative containing 4-methyl-1, 2, 3-thiadiazole and a preparation method and application thereof. The invention relates to heterocyclic compounds containing 1, 2, 3-thiadiazole. The compounds have the chemical structural formula shown as V. The invention discloses the structural formula and synthesis method of the compounds and application of the compounds as insecticide, insecticide and bactericide, as well as a processing process for preparing insecticide, insecticide and bactericide by using the mixture of the compounds and agriculturally acceptable assistants or synergists. The invention further discloses joint applicaiton of the compounds and the commercial insecticide, insecticide and bactericide, plant virus agents and plant activators for preventing and treating agricultural, forestal and gardening diseases, insect pests, acarid diseases and virus diseases as well as the preparation method.

Description

technical field [0001] The technical scheme of the present invention relates to containing 1,2-oxadiazole compound, specifically the 4,5-dihydrothiazole alkylate derivative of 4-methyl-1,2,3-thiadiazole, namely 2-(4 -Methyl-1,2,3-thiadiazol-5-yl)-4-(trifluoromethyl)-4,5-dihydrothiazol-4-ol carboxylate compounds. Background technique [0002] Viruses, fungi, bacteria, etc. are one of the important factors affecting modern agricultural production. Various diseases caused by these pathogens seriously affect the yield and quality of agricultural products. Various chemical fungicides are one of the important means to ensure the reduction of diseases and the yield and quality of agricultural products. However, in recent years, the widespread and unscientific use of various fungicides has caused various pathogenic bacteria in my country's farmland to produce obvious resistance to existing traditional fungicides (Jia Junchao, Ma Lin, Fan Zhijin, etc. Journal of Pesticide Science, 2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D417/14A01N43/828A01P7/04A01P3/00A01P1/00A01P7/02
Inventor 范志金毛武涛刘超伦李娟娟姬晓恬华学文宗广宁李凤云房震李岳东
Owner NANKAI UNIV
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