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Thiadiazole thiourea derivative as well as preparation and application thereof as plant growth regulator

A technology of thiadiazole and derivatives is applied to thiadiazole thiourea derivatives and their preparation and application fields as plant growth regulators, and can solve problems such as strong toxicity

Active Publication Date: 2013-04-24
菏泽建数智能科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But it was banned for being too toxic

Method used

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  • Thiadiazole thiourea derivative as well as preparation and application thereof as plant growth regulator
  • Thiadiazole thiourea derivative as well as preparation and application thereof as plant growth regulator
  • Thiadiazole thiourea derivative as well as preparation and application thereof as plant growth regulator

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0040] Example 1: Preparation of N-(5-(2,5-dichlorophenyl)-N'-(4-methyl-1,2,3-thiadiazol-5-yl)-thiourea

[0041] In a 100mL round bottom flask, add 0.97g (10mmol) of NH 4 NCS dichloromethane PEG-600 solution (10mL, including 9.5 mL dichloromethane and 0.5 mL PEG-600), stirred and refluxed for 15 minutes, left to cool, and suction filtered to obtain an orange solution, and added 10 mmol of the above method 2,5-Dichloroaniline was dissolved in 5 mL of anhydrous acetonitrile, stirred at room temperature for 10 h, allowed to stand overnight, filtered with suction, and the filter cake was recrystallized with a mixed solvent of DMF and water at a volume ratio of 1:1 to obtain the product.

[0042] Yellow solid, yield 85.9 %, melting point%: 181-183 ℃; 1 H NMR: 8.35 (s, 1H, NH), 8.14 (s, 1H, NH), 7.39-7.44 (m, 1H, Ph), 7.18-7.30 (m, 1H, Ph), 7.13-7.17 (m, 1H , Ph), 2.81 (s, 3H, CH 3); ESI-MS: 346 (M-1) ; Anal. calcd. For C 11 h 8 Cl 2 N 4 OS 2 : C 38.05, H 2.32, N 16.13; fou...

example 2

[0043] Example 2: Preparation of N-(5-(4-fluorophenyl)-N'-(4-methyl-1,2,3-thiadiazol-5-yl)-thiourea

[0044] In a 100mL round bottom flask, add 0.97g (10mmol) of NH 4 NCS dichloromethane PEG-600 solution (10mL, of which dichloromethane 9.5 mL, PEG-600 0.5 mL), stirred and refluxed for 15min, left to cool, suction filtered to obtain an orange solution, added the prepared 10mmol 4- Dissolve fluoroaniline in 5 mL of anhydrous acetonitrile, stir at room temperature for 10 h, let stand overnight, filter with suction, take the filter cake and recrystallize it with a mixed solvent of DMF and water at a volume ratio of 1:2 to obtain the product.

[0045] Yellow solid, yield 83.8 %, melting point: 166-168 ℃; 1 H NMR: 11.96 (s, 1H, NH), 10.00 (s, 1H, NH), 7.63-7.66 (m, 1H, Ph), 7.26-7.29 (m, 2H, Ph), 2.80 (s, 3H, CH 3 ); ESI-MS: 295 (M-1) ; Anal. calcd. For C 11 h 9 FN 4 OS 2 : C 44.58, H 3.06, N 18.91; found: C 44.46, H 3.13, N 18.76.

example 3

[0046] Example 3: Preparation of N-(5-(3-nitrophenyl))-N'-(4-methyl-1,2,3-thiadiazol-5-yl)-thiourea

[0047] In a 100mL round bottom flask, add 0.97g (10mmol) of NH 4 NCS dichloromethane PEG-600 solution (10mL, of which dichloromethane 9.5 mL, PEG-600 0.5 mL), stirred and refluxed for 15min, left to cool, suction filtered to obtain an orange solution, added the prepared 10mmol 3- Nitroaniline was dissolved in 10 mL of anhydrous acetonitrile, stirred at room temperature for 10 h, allowed to stand overnight, filtered with suction, and the filter cake was recrystallized with a mixed solvent of DMF and water at a volume ratio of 2:1 to obtain the product.

[0048] Yellow solid, yield 85.8 %, melting point: 115-117 ℃; 1 H NMR: 12.20 (s, 1H, NH), 8.71 (s, 1H, NH), 8.13 (m, J =8.48Hz, 1H, Ph), 8.02 (d, J =7.72Hz, 1H, Ph), 7.71 (t, J =8.09Hz, 1H, Ph), 2.82 (s, 3H, CH 3 ); ESI-MS: 322 (M-1) ; Anal. calcd. For C 11 h 9 N 5 o 3 S 2 : C 40.86, H 2.81, N 21.66; found: C 40.89, H...

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Abstract

The invention discloses an N-4-methyl-1,2,3-thiadiazol-4-acyl-N-substituted phenyl thiourea derivative (I), and discloses a preparation method and an application of the N-4-methyl-1,2,3-thiadiazol-4-acyl-N-substituted phenyl thiourea derivative as a plant growth regulator. The invention provides the new N-4-methyl-1,2,3-thiadiazol-4-acyl-N-substituted phenyl thiourea derivative, and provides the preparation method and application thereof. The N-4-methyl-1,2,3-thiadiazol-4-acyl-N-substituted phenyl thiourea derivative provided by the invention has excellent plant-growth regulating activity.

Description

[0001] (1) Technical field [0002] The invention relates to an N-4-methyl-1,2,3-thiadiazole-4-acyl-N-substituted phenylthiourea derivative and its preparation method and application. (2) Background technology [0003] Heterocyclic compounds have become the mainstream in the development of new pesticides, and more than 90% of the newly developed pesticides are heterocyclic pesticides. Among the heterocyclic compounds, nitrogen-containing heterocyclic rings are the main ones. In recent years, the plant inducer thiadinal, BTH has been successfully developed and marketed, which has aroused everyone's research on thiadiazole compounds. [0004] [0005] Thiourea compounds have various biological activities. Many literatures report that thiourea derivatives have a wide range of biological activities and are used in the fields of medicine and pesticides. Some thiourea compounds have been developed into commercial pesticides, such as the fungicide thiophanate (1). In the so...

Claims

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Application Information

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IPC IPC(8): C07D285/06A01N47/34A01P21/00
Inventor 刘幸海曹耀艳翁建全谭成侠刘会君
Owner 菏泽建数智能科技有限公司
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